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100 worst romantic comedies of all time

  • 1/ Entertainment Pictures / Alamy Stock Photo

    100 worst romantic comedies of all time

    From Ernst Lubitsch and Billy Wilder, to Nora Ephron and Nancy Meyers, there’s so much to love about the romantic comedy genre. How can we forget the iconic lines whispered into lovers’ ears the moment they’re finally united onscreen, or better yet, how can we live our own lives thinking we’re not somehow eventually going to end up with our own version of a meet-cute-turned-romance?

    Given our commitment to smart, beautiful romcoms and the legends who both designed and protected the genre for decades, it’s heartbreaking to see it gutted by clunkers that don’t quite hit the right mark. Between poor acting performances, inadequate scripts and comedy that simply doesn’t have a punch, it’s been said that studios have ample reason to largely abandon the form. Only the studios seem to think that the problem is in the audience, not the talentless sauce of recent attempts at ill-fated remakes and confused romcom mashups.

    To fully investigate this mess, Stacker has ranked the worst 100 romcom movies of all time (with the biggest offenders hovering within the last decade or so—take note, studio execs). For our analysis, we’ve built an index (the ‘Stacker Score’) that combines IMDb ratings and Rotten Tomatoes Audience Scores. To qualify, a film needed to have at least 1,500 IMDb votes. Stacker Scores are based on a 1-100 scale; and now, we present the 100 worst romantic comedy movies of all time.

  • 2/ MWM (MadisonWellsMedia)

    #100. From Prada to Nada

    Stacker Score: 38.00

    IMDb rating: 5.5

    Tomatometer: 21%

    This Latin spin on Jane Austen’s classic Sense & Sensibility was perhaps ahead of its time. Released in 2011, wealthy sisters Nora and Mary are transported from Rodeo Drive to East LA after their father suddenly dies. Critics found the modern update too predictable and forced, and wrapped up in too many clichés. Few viewers came for the romance nor the comedy; the limited release film grossed only $3 million.

  • 3/ Universal Pictures

    #99. You, Me and Dupree

    Stacker Score: 38.00

    IMDb rating: 5.6

    Tomatometer: 20%

    Using what Roger Ebert called “the idiot plot,” this Russo brothers (Arrested Development) 2006 film couldn’t be saved by Kate Hudson’s nor Owen Wilson’s charm. Hudson and Matt Dillon are newlyweds, with Wilson in the titular role of Randy “Dupree”—a most unwelcome guest who comes between the happy couple in more ways than one with silly gimmicks and humor that doesn’t quite land. The film brought in $75.6 million at the domestic box office on a $54 million budget.

  • 4/ Lionsgate

    #98. Employee of the Month

    Stacker Score: 37.50

    IMDb rating: 5.5

    Tomatometer: 20%

    Shot at a local Costco store in Albuquerque, New Mexico, comedian Dane Cook and Jessica Simpson starred as employees at the fictional “Superclub,” where Cook is vying for her heart and the title at work that gives the film its namesake. They both heavily promoted the film, hosting the Teen Choice Awards together and getting Cook booked to open the season of Saturday Night Live as host. While Cook’s performance was likable, Simpson earned herself a Razzie Award nomination, losing out to Sharon Stone for her performance in Basic Instinct 2.

  • 5/ Warner Bros.

    #97. Rumor Has It...

    Stacker Score: 37.50

    IMDb rating: 5.5

    Tomatometer: 20%

    Directed by Rob Reiner (When Harry Met Sally) and based on a premise related to Mike Nichols’ groundbreaking 1967 hit The Graduate, this film should have been at least decent, particularly given the starpower of the cast, which included Jennifer Aniston, Kevin Costner and Shirley MacLaine. But it was panned for being too bland and even creepy by some, earning a modest $89 million on a $70 million budget.

  • 6/ Twentieth Century Fox

    #96. Just Married

    Stacker Score: 37.50

    IMDb rating: 5.5

    Tomatometer: 20%

    The late Brittany Murphy stars with Ashton Kutcher in this lovable 2003 comedy about two newlyweds navigating the realities of holy matrimony on their honeymoon while a number of issues bubble up—some funny, some not. A box office success, critics were not impressed with the predictable storyline, and both actors earned Razzie Award nominations individually and as a couple.

  • 7/ New Line Cinema

    #95. Valentine's Day

    Stacker Score: 37.50

    IMDb rating: 5.7

    Tomatometer: 18%

    Sadly, Valentine’s Day, one of the last films of the late iconic director and producer Garry Marshall, left critics frustrated with the lame dialogue and scenes that “didn’t last longer than a New York minute.” The all-star ensemble cast (Julia Roberts, Ashton Kutcher, Jennifer Garner, Patrick Dempsey, Taylor Swift and more) find and lose love throughout the film’s namesake holiday. Still, it was a huge box office success, opening No. 1 and raking in $110 domestically.  

  • 8/ Fox Searchlight Pictures

    #94. I Think I Love My Wife

    Stacker Score: 37.00

    IMDb rating: 5.5

    Tomatometer: 19%

    With a screenplay by comedian Louis C.K. (pre-disgraced-status) and Chris Rock (who also directed), plus Kerry Washington (Scandal) and Rock playing lovers onscreen, one might assume I Think I Love My Wife (a remake of the 1972 film Chloe in the Afternoon) would be a hit —but no such luck. Critics panned the punch-line-driven screenplay and thought Rock’s character ended up looking more pathetic than empathetic, as he wandered into the world of cheating with a too-scantily-clad Washington for their liking.

  • 9/ The Weinstein Company

    #93. The Ex

    Stacker Score: 37.00

    IMDb rating: 5.5

    Tomatometer: 19%

    Amanda Peet plays the pregnant wife to slacker Zach Braff in The Ex, but their romance is sidetracked by a film whose comedy was described by critics as “half-baked.” Despite praise for Braff and co-star Jason Bateman, the marketing for the movie as a romcom never seemed to quite fit, and the finished product was so bad, the screenwriters essentially disowned it. It grossed only $5 million overall.

  • 10/ Revolution Studios

    #92. Little Black Book

    Stacker Score: 37.00

    IMDb rating: 5.3

    Tomatometer: 21%

    When a cameo by Carly Simon can’t save your movie, you know you’re in trouble. This 2004 film starred the late Brittany Murphy (Clueless), who looked into the “little black book” of her commitment-phobic boyfriend played by Ron Livingston (Office Space) in order to learn more about his past. Critics for the most part didn’t give praise for Murphy’s acting or for the script, and it lost money for Sony at the box office.

  • 11/ Paramount Pictures

    #91. Grease 2

    Stacker Score: 37.00

    IMDb rating: 4.2

    Tomatometer: 32%

    John Travolta and Olivia Newton-John are a tough act to follow, even if you’re Michelle Pfeiffer. This 1982 sequel just felt like recycled materials without the stars, said critics, while it seemed to please about half of the audience (except for Newton-John, who eviscerated it). Patricia Birch, who choreographed the original musical romcom hit, directed the deflated sequel.

  • 12/ BET Pictures

    #90. Diary of a Mad Black Woman

    Stacker Score: 36.50

    IMDb rating: 5.7

    Tomatometer: 16%

    In Tyler Perry’s feature film debut, Diary of A Mad Black Woman, viewers first get to meet grandmother Madea (played by Perry), who would later take on her own set of franchise films. But it’s Madea’s sassiness that steals too much of the show in what could have been a romantic dramedy focused on the blossoming love affair of newly separated Helen (Kimberly Elise) and Orlando (Shemar Moore, Criminal Minds). Perry’s popular stage play of the same name resonated with audiences, but not with critics, who didn’t care for the confusing mashup of genres.

  • 13/ Columbia Pictures

    #89. Aloha

    Stacker Score: 36.50

    IMDb rating: 5.4

    Tomatometer: 19%

    Awash in the whitewashing controversy caused by miscasting Emma Stone, Aloha couldn’t rise up despite an all-star cast (Rachel McAdams, Bradley Cooper, Bill Murray, among other A-listers) and famed director Cameron Crowe’s best efforts. Set in Hawaii (though no native Hawaiians are present), one critic said it was “paced like a record on the wrong speed,” and “Crowe’s worst film.” It was a bomb for Sony, who lost an estimated $65 million when all was said and done.

  • 14/ Warner Bros.

    #88. Her Alibi

    Stacker Score: 36.00

    IMDb rating: 5.7

    Tomatometer: 15%

    A “bad” mystery writer (Tom Selleck) gets swept up by the affections of Nina (Paulina Porizkova), a beautiful immigrant he presumes is wrongfully accused of murder until a series of failed gimmicks raise doubts in this forgettable 1989 farce. Roger Ebert gave it a half star, calling it “endless, pointless and ridiculous.” It grossed only $18 million at the domestic box office. 

  • 15/ Caravan Pictures

    #87. I Love Trouble

    Stacker Score: 36.00

    IMDb rating: 5.2

    Tomatometer: 20%

    Competing journalists (Julia Roberts and Nick Nolte) must learn to trust each other and work together when they discover a dark scandal—and build some chemistry in the process. But critics found the thriller subplot too distracting despite Roberts’ graceful performance, and it didn’t help that Nolte and Roberts didn’t get along on set, each calling it the worst experience of their careers.

  • 16/ Touchstone Pictures

    #86. When in Rome

    Stacker Score: 36.00

    IMDb rating: 5.6

    Tomatometer: 16%

    Top critics didn’t care for the dullness and lack of depth in this Kristen Bell and Josh Duhamel-helmed Disney flick. Bell is a New Yorker who has given up on romance until she throws some “magic” coins into a fountain in Rome and finds herself with more strange suitors to choose from than stars in the reviews, sadly. Dax Shepard (Bell’s husband), Will Arnett and Jon Heder all throw their hats in the ring, and some viewers found it hard not to like Bell’s performance, but ultimately, the film’s over-reliance on clichés left critics wanting more.

  • 17/ Columbia Pictures

    #85. Whatever It Takes

    Stacker Score: 35.50

    IMDb rating: 5.5

    Tomatometer: 16%

    A young James Franco and Shane West couldn’t save this teen update of the classic Cyrano de Bergerac tale, in which nerdy West falls for the cute, popular girl in school, and Franco looks for help from West in getting the attention of his best friend and fellow nerdy pal, Maggie (Marla Sokoloff). Critics panned it, and the movie was a commercial flop, bringing in only $9 million at the domestic box office, well below its $32 million budget.

  • 18/ Lila 9th Productions

    #84. Syrup

    Stacker Score: 35.50

    IMDb rating: 5.7

    Tomatometer: 14%

    In a blend of social satire and romantic comedy, Syrup didn’t quite stick with critics despite the popular source material (Max Barry’s novel of the same name). Amber Heard stars as Six, the business partner and love interest of ambitious marketing executive Scat, who comes up with a million-dollar idea, but can’t seem to see it through due to trust issues with his new love. The VOD release raked in more than $600 million domestically on a $25 million budget, but critics panned it for a sluggish script and unsatisfying commentary.

  • 19/ CBS Films

    #83. The Back-up Plan

    Stacker Score: 35.50

    IMDb rating: 5.3

    Tomatometer: 18%

    Jennifer Lopez stars as a single New York woman who meets Mr. Right just a little too late: She’s just visited a sperm bank and is expecting twins when he turns up. What ensues is a mildly amusing but less-than-original romcom that left critics displeased with the script and audiences somewhat disinterested overall after the movie was leaked online days before its release in 2010.

  • 20/ New Line Cinema

    #82. Monster-in-Law

    Stacker Score: 35.50

    IMDb rating: 5.5

    Tomatometer: 16%

    The "evil mother-in-law" trope takes center stage in this film starring Jennifer Lopez. The mother of her love interest sets out to ruin their relationship when things in her own personal and professional life spiral out of control. Her attempt to destroy their relationship is seen by viewers as a bit trite, but the film still did well at the box office earning $83 million domestically. 

  • 21/ Columbia Pictures

    #81. The Wedding Planner

    Stacker Score: 34.50

    IMDb rating: 5.3

    Tomatometer: 16%

    Critics wanted to love this 2001 film led by megastars Jennifer Lopez and Matthew McConaughey, but they couldn’t buy in to the premise in the end, despite first-time director Adam Shankman’s best efforts to pull it off. Lopez, the wedding planner, finds herself in an obnoxious meet-cute with McConaughey by getting her high heel caught on the street and nearly going face first into a dumpster before he catches her. Acclaimed critic Roger Ebert would have preferred Ben Affleck or Alec Baldwin in the role to make the material work.

  • 22/ Crossfire Sound & Pictures

    #80. Waking Up in Reno

    Stacker Score: 34.00

    IMDb rating: 5.5

    Tomatometer: 13%

    This redneck romcom, co-produced by country singer Dwight Yoakam, centers on infidelity between two trashy couples on their way to see a monster truck show in Reno. Charlize Theron, Patrick Swayze, Natasha Richardson and Billy Bob Thornton top off the bill. Despite the best efforts of the eclectic cast, the script’s hillbilly humor didn’t fly with most critics, and audiences largely ignored the yokel-fest, which flopped at the box office.

  • 23/ High School Sweethearts

    #79. The Beautician and the Beast

    Stacker Score: 34.00

    IMDb rating: 5.3

    Tomatometer: 15%

    A New York City cosmetologist, through a series of mixups, is hired to educate the children of an ornery Eastern European dictator. Fran Drescher plays the female lead with the same nasal ditziness she employed in the TV show The Nanny. Timothy Dalton plays her unlikely employer, with whom things soon take a romantic turn. Critics chastised Drescher for playing so safely within her wheelhouse, and audiences, not finding much new on display, stayed home. The final take was $11 million domestically.

  • 24/ Touchstone Pictures

    #78. My Father the Hero

    Stacker Score: 34.00

    IMDb rating: 5.4

    Tomatometer: 14%

    This is a remake that, along with the story, borrows the star from the French original. Gerard Depardieu reprises his role as an absentee father who tries to mend his relationship with his daughter (a young Katherine Heigl) by taking her on vacation to the Bahamas. Unbeknownst to him, however, his daughter tells their fellow vacationers that he is her lover and an ex-con. Critics balked at the iffy premise and the heavy reliance on double entendre humor. The box office take was $25 million.

  • 25/ Fine Line Features

    #77. Feeling Minnesota

    Stacker Score: 34.00

    IMDb rating: 5.4

    Tomatometer: 14%

    The title of this comes from the 1996 Soundgarden song "Outshined," which features the line "I'm looking California / and feeling Minnesota." The story centers on a stripper (Cameron Diaz) being strong-armed into marrying a sleazebag (Vincent D'Onofrio) and then skipping town with his ex-con brother (Keanu Reeves). Although the movie had its sights set on being a black comedy, critics found zero laughs to add any buoyancy to the cliché story beats. It grossed only $3 million.

  • 26/ Twentieth Century Fox

    #76. Fat Albert

    Stacker Score: 34.00

    IMDb rating: 4.3

    Tomatometer: 25%

    This 2004 live-action adaptation of the ’70s and ’80s cartoon Fat Albert and the Cosby Kids (created, produced, voiced and hosted by Bill Cosby) stars SNL’s longest-running cast member, Kenan Thompson, in the titular role. The story sees the animated Fat Albert (and his pals) magically stepping out from the world of the TV show to help a struggling teenage girl deal with not fitting in. Once in the real world, Fat Albert falls in love with the girl’s foster sister. Critics were split: Some gave the film a pass for its harmlessness, but others found it too lame even for kiddie fare. Several remarked on the Bill Cosby cameo as a touching highlight, an assessment that surely would not fly in 2018. Box office receipts totalled a somewhat-hefty $48.12M.

  • 27/ TriStar Pictures

    #75. High School High

    Stacker Score: 34.00

    IMDb rating: 5.5

    Tomatometer: 13%

    Jon Lovitz plays a teacher at a snooty private academy who gives up his job to take a position at a tough urban school, where he becomes enamored with a fellow teacher played by Tia Carrere. Of all the films on this list, this one features the least buyable chasm in attractiveness between its romantic leads, which is maybe forgivable since it’s meant to be a farcical sendup of serious dramas in the Dangerous Minds vein. But critics found the jokes too reliant on dated references to ’70s movies for the satire to sustain interest. U.S. box office was a C-minus worthy $20.95M.

  • 28/ Metro-Goldwyn-Mayer (MGM)

    #74. Sleepover

    Stacker Score: 34.00

    IMDb rating: 5.3

    Tomatometer: 15%

    Four unpopular high school girls have a sleepover that turns into an all-night scavenger hunt against a rival cool girl clique. Critics found this tween-oriented fluffball excruciating to sit through, citing the romance subplot as particularly saccharine. To give an idea of how lazy this movie is, consider this: The lead “mean cool girl” is actually named Staci. Domestic box office did not reach $10M.

  • 29/ New Regency Pictures

    #73. Just My Luck

    Stacker Score: 34.00

    IMDb rating: 5.4

    Tomatometer: 14%

    This 2006 screwball romcom failed to right Lindsay Lohan’s tabloid-mired career. Lohan’s character Ashley is a happy-go-lucky success until a magic party kiss with perpetually unlucky Jake (Chris Pine) switches their fortunes. Critics found the picture insipid, pointing out that many of the scenes intended to portray “bad luck” really just showcased Ashley’s stupidity. Fortune did not favor the box office take, which came in at an unprofitable $17.32M

  • 30/ Warner Bros.

    #72. Fool's Gold

    Stacker Score: 34.00

    IMDb rating: 5.7

    Tomatometer: 11%

    Amazingly, this is the first Matthew McConaughey film on this list. The movie sees the breezy Texan re-teaming with his How to Lose a Guy in 10 Days co-star Kate Hudson (who, conversely, has already graced this list several times). The plot centers around a recently-divorced treasure hunting duo who rekindles their marriage through the search for a legendary haul of sunken booty. Critics found the charming moments too spaced out and the characters underdeveloped. Despite its mediocrity, the movie managed to loot $70.23M from the box office.

  • 31/ Columbia Pictures

    #71. Sex Tape

    Stacker Score: 34.00

    IMDb rating: 5.1

    Tomatometer: 17%

    Jason Segel and Cameron Diaz play a married couple who attempt to spice up their boring love life by making a sex tape. When the footage (which has them assuming every position listed in The Joy of Sex) falls into the wrong hands, they embark on a one-night quest to reclaim it. Despite its R-rating, critics chided the film for having a PG sensibility and being too gun-shy to capitalize on its premise. Banking only $38.54M, the movie failed to perform.

  • 32/ Columbia Pictures

    #70. The Bounty Hunter

    Stacker Score: 34.00

    IMDb rating: 5.5

    Tomatometer: 13%

    The plot of this 2010 film is a grab bag of recycled concepts: A bounty hunter (Gerard Butler) is tasked with bringing in his bail-skipping ex-wife (Jennifer Aniston) but instead finds himself caught up in her attempt to solve a high-profile murder. Critics dismissed the film as assembly-line Hollywood product and snubbed the phoned-in performances. Even so, the film made $67.06M at the box office, turning a profit.

  • 33/ Columbia Pictures

    #69. Mo' Money

    Stacker Score: 33.50

    IMDb rating: 5.4

    Tomatometer: 13%

    A small-time crook played by Damon Wayans tries to go straight to win over a girl (Stacey Dash) but is drawn back into a life of crime when he steals one last credit card in order to impress her with a shopping spree. Bernie Mac, in his feature film debut, plays a doorman. The film, whose cast also includes Marlon Wayans in a supporting role, debuted at No. 1 at the U.S. box office, despite poor critical reception. Reviewers saw the attempt to combine action, comedy and romance as an overreach, resulting in a watered-down final product. Failing to heed the poor reviews, filmgoers were swindled out of $40.23M.

  • 34/ Emmett/Furla/Oasis Films (EFO Films)

    #68. Lay the Favorite

    Stacker Score: 33.50

    IMDb rating: 4.8

    Tomatometer: 19%

    Based on a memoir of the same name by Beth Raymer, Lay the Favorite follows the story of a free-spirited woman navigating the high-stakes world of sports gambling and getting into various romantic entanglements along the way. Rebecca Hall plays Beth, with Bruce Willis filling the role of her mentor (and one of the film’s two love interests) in a supporting role. Critics bet against the film, citing a disconnected story that never built momentum. Audiences stayed away—the movie grossed less than a million dollars at the box office. Not a good payout.

  • 35/ Lakeshore Entertainment

    #67. The Next Best Thing

    Stacker Score: 33.50

    IMDb rating: 4.7

    Tomatometer: 20%

    Madonna and Rupert Everett (who co-wrote the screenplay) star in this comedy about a straight woman and a gay man who decide to conceive and raise a child together. Critics found the delivery heavy-handed and the tearjerker moments forced. The $14.99M box office receipts did little to convince producers that Madonna was a bankable star outside the music business.

  • 36/ Epsilon Motion Pictures

    #66. Alex & Emma

    Stacker Score: 33.50

    IMDb rating: 5.6

    Tomatometer: 11%

    This Is Spinal Tap and Princess Bride director Rob Reiner failed to inject any laughs or charm into this 2003 paint-by-numbers romcom starring Kate Hudson and Luke Wilson. Wilson plays an author scrambling to complete a novel in 30 days in order to meet his deadline to pay back some murderous loan sharks. Hudson plays the stenographer he hires to help him complete this task. Their collaboration develops into a predictable romance. Critics sniped at the unrealistic portrayal of the publishing industry and the writing life, and generally reported finding the comedy flat. Its characters may have escaped their debt by the closing credits, but box office receipts of only $14.21M left this picture in the red.

  • 37/ Gold Circle Films

    #65. Over Her Dead Body

    Stacker Score: 33.50

    IMDb rating: 5.2

    Tomatometer: 15%

    The plot revolves around a ghost (Eva Longoria) trying to sabotage a relationship between her former fiance (Paul Rudd) and a psychic (Lake Bell). Critics called it a lightweight Ghost and found the pacing slow, the plot implausible and the characters lacking in charm. Making only $7.56M, this one vapored off the mortal plane without leaving much of a trace.

  • 38/ Fox Atomic

    #64. I Love You, Beth Cooper

    Stacker Score: 33.50

    IMDb rating: 5.3

    Tomatometer: 14%

    Based on a novel of the same name by former Simpsons writer Larry Doyle, this 2009 teen romcom stars Hayden Panettiere and Paul Rust as the romantic leads. The plot kicks off with a nerdy graduating senior declaring his love for the prettiest girl in school during his valedictorian speech. To his great shock, that evening she shows up at his door to take him out on a wild night. Critics dubbed Rust’s performance overly weird and felt the rest of the cast lacked the comedy chops to land the script’s jokes. It underperformed at $14.79M.

  • 39/ MWM (MadisonWellsMedia)

    #63. Mortdecai

    Stacker Score: 33.50

    IMDb rating: 5.5

    Tomatometer: 12%

    This action/comedy slots in some romcom elements. Mortdecai (Johnny Depp) is an art dealer tasked with tracking down a painting rumored to contain the code to a trove of Nazi gold. His adventures lead to romantic complications with his wife (Gwyneth Paltrow) along the way. By 2015, critics and audiences alike were burned out on Depp playing one caricature after another. Reviews commented on the strained attempts at comedy and felt the character was too old-fashioned to resonate with audiences. The strange spelling of his name also hampered SEO marketing. Pulling in only $7.61M domestically, Mortdecai was a massive financial flop.

  • 40/ Balcor Film Investors

    #62. Soul Man

    Stacker Score: 33.00

    IMDb rating: 5.2

    Tomatometer: 14%

    A white college student (C. Thomas Howell), hellbent on attending Harvard Law at any cost, darkens his skin to gain eligibility for a scholarship for African Americans. The premise makes the film sound like a polemical against affirmative action, but actually the script has Howell’s character learning life lessons about bigotry as he falls for an African-American student (played by Rae Dawn Chong, daughter of stoner comedian Tommy Chong). Nevertheless, the image of a Canadian actor in what was essentially blackface onscreen riled some members of the black community. Spike Lee spoke out against the film (without having seen it), the NAACP publicly denounced the movie as “racist,” and some screenings were picketed. Upon its release, Roger Ebert acknowledged that the idea was “genuinely interesting” but thought the delivery lacked “true moral courage,” preferring to opt for sitcom humor rather than mining the depths of its premise. It’s difficult to say whether the $27.82M gross was helped or hurt by the controversy, but given the movie’s low budget, it amounted to a healthy profit.

  • 41/ IFC Films

    #61. I Hate Valentine's Day

    Stacker Score: 33.00

    IMDb rating: 4.7

    Tomatometer: 19%

    IFC Films attempted to capitalize on the runaway success of My Big Fat Greek Wedding by re-teaming its co-stars Nia Vardalos and John Corbett for this 2009 romcom. The concept and story are totally boilerplate: A woman with a “five-date max” rule is forced to reconsider when she meets a guy worth going the distance for. Critics thought the dating, as portrayed, was outdated and, at best, considered it a cheap guilty pleasure. Audiences barely noticed it: Gross was less than a million dollars at the box office.

  • 42/ Sherwood Productions

    #60. Blame It on Rio

    Stacker Score: 33.00

    IMDb rating: 5.7

    Tomatometer: 9%

    An aging executive played by Michael Caine is surprised to find the attractive daughter of his best friend coming onto him on vacation. Caine churned out a lot of movies in the ’80s, and this 1984 release is one of his least distinguished outings. It managed to double its budget in domestic returns of $18.64M, despite the fact that even at the time, critics found the script creepy in its endorsement of dirty old man behavior. Needless to say, the film has not aged well and probably wouldn’t have a chance of being made today.

  • 43/ 10th Hole Productions

    #59. The Romantics

    Stacker Score: 33.00

    IMDb rating: 5.1

    Tomatometer: 15%

    Conflict brews in the lead up to a wedding whose bride (Anna Paquin) and maid of honor (Katie Holmes) have had a longtime rivalry over the groom. The writer of the novel the film is based on adapted the screenplay and directed the feature, which came and went in limited release with a box office of around $100K.

  • 44/ New Regency Pictures

    #58. Simply Irresistible

    Stacker Score: 33.00

    IMDb rating: 5.3

    Tomatometer: 13%

    Sarah Michelle Gellar stars as an heiress to a restaurant who is blessed with magical cooking and seduction abilities by a crab in a tuxedo. The title begs for oppositional review bylines, which critics were eager to deliver given that the plot never rises above its absurd premise. Domestic grosses of $4.39M reflected a disconnected marketing campaign. A somewhat ominous movie poster featured Gellar pouting in front a full moon, a tableau that was perhaps attempting to recall her iconic TV role in Buffy The Vampire Slayer but wasn’t in the least bit reflective of the film’s goofy tone.

  • 45/ Media 8 Entertainment

    #57. Lovewrecked

    Stacker Score: 33.00

    IMDb rating: 4.9

    Tomatometer: 17%

    Amanda Bynes stars as a teen who ends up marooned on a desert island with the rock star she has a crush on. The rub is, they’re only stranded a few miles from a luxury resort, a fact she knows but is eager to keep secret in the hopes that a tropical romance will blossom. Critics shrugged this one off as teenybopper fluff that sent a questionable message to its target audience. The gross was a meager $480K.

  • 46/ Miramax

    #56. View from the Top

    Stacker Score: 33.00

    IMDb rating: 5.2

    Tomatometer: 14%

    An aspiring stewardess (Gwyneth Paltrow) juggles grueling flight training with the romantic pursuit of a law student (Mark Ruffalo). Critics found the low stakes better suited to a straight-to-video release and criticized technical elements of the film, such as its editing, as amateurish. The release, initially scheduled for 2001, was pushed back two years in the wake of 9/11 in an effort to put some distance between the national tragedy and the film’s subject matter. The film, which grossed $15.59M domestically, never made back its production budget.

  • 47/ Columbia Pictures

    #55. Zookeeper

    Stacker Score: 33.00

    IMDb rating: 5.2

    Tomatometer: 14%

    Kevin James. Is there an actor alive whose box office success is more incongruous with critics’ distaste for his movies? In this PG romcom, James plays a kindly zookeeper who discovers animals can talk—and offer courtship advice—when he considers quitting his job and his wards are forced to break their code of silence. Film critic Leonard Maltin thought it was a step up from James’ previous project, Paul Blart: Mall Cop, but the majority of reviewers disagreed. The picture grossed $80.36M domestically, less than its production budget, but strong overseas numbers brought its international total to a profitable $169.8M worldwide.

  • 48/ Dante Entertainment

    #54. Avenging Angelo

    Stacker Score: 32.50

    IMDb rating: 5.2

    Tomatometer: 13%

    This 2002 Martin Burke-directed misfire starring Sylvester Stallone made the mistake of trying to jam too much into the box. Its attempts to combine action, romance and comedy into a single package resulted in a confused jack-of-all trades that critics rejected even while acknowledging that Sly was overdue for a better role. The story centers on a mafia daughter who enlists her slain father’s bodyguard to help avenge his death. Like the previous entry in this list, box office numbers are slight enough that they’re not posted on the typical outlets for such information.

  • 49/ Armian Pictures

    #53. The Longest Week

    Stacker Score: 32.50

    IMDb rating: 5.4

    Tomatometer: 11%

    Conrad Valmont (Jason Bateman), an aimless rich guy, is evicted from his parents’ Manhattan hotel and in the space of a week finds himself disinherited and falling in love with the gorgeous Beatrice (Olivia Wilde). The film—snarky, pretentious and smug—was criticized for copping heavily from superior Wes Anderson and Woody Allen movies. Box office performance was so low that numbers are not readily available.

  • 50/ Punch 21 Productions

    #52. Boys and Girls

    Stacker Score: 32.50

    IMDb rating: 5.4

    Tomatometer: 11%

    OK, seriously, how has Freddie Prinze Jr. been allowed to make so many of these stinkers? The nuts-and-bolts title aptly previews the incredibly simplistic plot—two longtime friends (played by Prinze Jr. and Claire Forlani) discover their romantic feelings for each other over four years in college. Prinze Jr.’s performance continued his long streak of unwavering blandness. Critics hated it. Domestic gross was $20.63M 
     

  • 51/ Fox 2000 Pictures

    #51. Bride Wars

    Stacker Score: 32.50

    IMDb rating: 5.5

    Tomatometer: 10%

    Two best friends (Kate Hudson and Anne Hathaway) become engaged in a bridezilla showdown when, due to a clerical error, they accidentally schedule their weddings on the same day. This 2009 movie drew plenty of ire from critics who, fed up with the overdone wedding movie genre, pounced on the film’s superficiality and disdain for its audience. Said audience showed up anyway, netting the picture a profitable $58.72M.

  • 52/ Alcon Entertainment

    #50. Love Don't Cost a Thing

    Stacker Score: 32.00

    IMDb rating: 5.1

    Tomatometer: 13%

    Nick Cannon had pulled off a lauded star turn in the previous year’s Drumline, but his sophomore attempt at carrying a picture was a letdown. The movie is a remake of the 1987 teen comedy "Can't Buy Me Love" but with a (mostly) African American cast. Cannon plays a budding engineer who, in a bid for high school popularity, agrees to repair a popular cheerleader’s car on the condition that she pretend to be his girlfriend for two weeks. Critics found it had little to offer over the original and that the script was trying way too hard to be cool. The $21.9M box office receipts were less than half that of Drumline.

  • 53/ New Line Cinema

    #49. Even Cowgirls Get the Blues

    Stacker Score: 32.00

    IMDb rating: 4.3

    Tomatometer: 21%

    This film, based on a beloved Tom Robbins novel with strong feminist themes, was supposed to be indie director Gus Van Sant’s triumphant follow up to My Own Private Idaho. It’s a movie with a lot of intriguing ingredients: Uma Thurman stars as a woman who uses her unusually large thumbs to hitchhike her way across the country, winding up at a ranch staffed by cowgirls. There she has a love affair with the ranch’s leader, played by Rain Phoenix (sister to Joaquin and River Phoenix). Singer/songwriter K.D. Lang, an active gay rights activist, wrote and performed the soundtrack. Tom Robbins himself provided the narration. Despite the caliber of the source material and edgy (for 1994) exploration of gay themes, critics found little value in the finished product. Van Sant had no feel for the subject matter and drew out confusing and sometimes embarrassing performances from his actors. Box office receipts fell shy of $2M. Van Sant would have to wait a few more years for his first commercial hit, which arrived in 1997 with the smash career-maker Good Will Hunting.

     

  • 54/ Universal Pictures

    #48. Head Over Heels

    Stacker Score: 32.00

    IMDb rating: 5.4

    Tomatometer: 10%

    This is essentially Rear Window with a female lead who falls in love with the guy she thinks she’s seen commit a murder. Freddie Prinze Jr. was way too bubbly to inject the necessary darkness into the alleged killer character, and critics wrote the film off as a disposable teen date movie. It brought in only $10 million at the box office.

  • 55/ New Line Cinema

    #47. Mr. Woodcock

    Stacker Score: 32.00

    IMDb rating: 5.1

    Tomatometer: 13%

    Despite its solid premise—an author (Sean William Scott) races home to stop a wedding between his mother (Susan Sarandon) and the gym teacher (Billy Bob Thornton) who tormented him back in high school—this movie suffered from tone-deaf delivery. Many critics found it more depressing than humorous. It tanked with audiences, pulling in only $25 million.

  • 56/ Two Ton Films

    #46. The Big Wedding

    Stacker Score: 32.00

    IMDb rating: 5.6

    Tomatometer: 8%

    This 2013 remake of a 2006 Swiss/French film did not translate to American audiences. A long-divorced couple (Robert De Niro and Diane Keaton) are forced to pretend they’re still married in order to impress the conservative biological mother of their adopted son at his wedding. Critics found it more quirky than funny and balked at the overreliance on slapstick. Box office gross was $21.78M, less than 1/10th of what My Big Fat Greek Wedding pulled in (without a single movie star in the cast) in 2002.

  • 57/ New Line Cinema

    #45. New Year's Eve

    Stacker Score: 32.00

    IMDb rating: 5.7

    Tomatometer: 7%

    Man, Jessica Biel is in a lot of movies on this list. In this 2011 schlockfest, she joins an ensemble cast including Halle Berry, Abigail Breslin, Robert De Niro, and Josh Duhamel in a tale of intertwining love stories set on Dec. 31 in Manhattan. This was an obvious retread of Love Actually, but bereft of that film’s heart or humor, and critics saw straight through the producers’ cynicism, warning audiences to seek out other holiday options. Domestic gross was $54.54M, a poor showing for such a star-studded picture.

  • 58/ Lionsgate

    #44. Killers

    Stacker Score: 32.00

    IMDb rating: 5.4

    Tomatometer: 10%

    Katherine Heigl plays a newlywed who discovers her husband (Ashton Kutcher) is an assassin, a revelation that throws their marriage into turmoil. This 2010 clunker—Mr. and Mrs. Smith lite—turned off critics with its warmed over plot and plain dullness. The picture made $47.06M at the box office, a figure dwarfed by the conceptually similar Tom Cruise/Cameron Diaz double-header Knight and Day, which was released in the same month and proved a big commercial hit.

  • 59/ Photo 12 / Alamy Stock Photo

    #43. Lost & Found

    Stacker Score: 31.50

    IMDb rating: 5.0

    Tomatometer: 13%

    David Spade plays a restaurateur who steals a woman’s dog in the hopes of returning it to impress her, but his plan to win her affections backfires. The thin premise is good for about 15 minutes of comedy before the film devolves into meanness, stupidity and ripping off jokes from superior romcoms such as There’s Something About Mary. Spade, as co-writer of the script, was doubly implicated in this flop, which grossed only $6.55M. The poster, in a self-aware nod to its leading man’s public image as a weasley lech, features the former SNL’er holding the stolen mutt in front of his crotch with the tagline: “One of these dogs must be Spade.”

  • 60/ Alliance Atlantis Communications

    #42. Slackers

    Stacker Score: 31.50

    IMDb rating: 5.3

    Tomatometer: 10%

    No relation to Richard Linklater’s pioneering 1991 mumblecore flick Slacker, this 2002 college comedy failed to rise above the glut of early 2000s teen gross-out fare. A geeky Jason Schwartzman blackmails a scheming Devon Sawa (and his two equally sheisty buddies) into setting him up with the girl he’s obsessed with. Sawa’s character falls for the girl in question (played by Jaime King) and hijinks ensue. This film was the product of the ill-fated Destination Films, a low-budget film company acquired by Sony Pictures Entertainment in 2001. Sony let this one sit on a shelf for a year before releasing it through their Screen Gems arm. A gem it was not. It grossed $4.81M.

  • 61/ Fox Searchlight Pictures

    #41. Our Family Wedding

    Stacker Score: 31.00

    IMDb rating: 4.9

    Tomatometer: 13%

    Two families—one African-American, one Mexican-American—clash in the moments before a wedding. America Ferrera and Lance Gross play the young couple, with Carlos Mencia and Forest Whitaker taking on the roles of the warring alpha dads. The film’s heavy reliance on racial stereotypes kills the comedy, and critics zeroed in on Mencia’s performance as especially grating. Domestic box office was $20.25M.

  • 62/ Yari Film Group (YFG)

    #40. The Accidental Husband

    Stacker Score: 31.00

    IMDb rating: 5.6

    Tomatometer: 6%

    A talented cast including Uma Thurman, Jeffrey Dean Morgan, Colin Firth, Sam Shephard and Isabella Rossellini is wasted on this lifeless romcom. A radio talk show host (Thurman) who advises a woman to break off her engagement must then contend with reprisal from the woman’s jilted fiance (Dean Morgan). In a tried-and-true application of the well-worn formula, the two leads proceed to bicker their way to a love connection. It’s in-flight movie caliber stuff at best, although perhaps more entertaining if you pretend Jeffrey Dean Morgan is playing a pre-zombie apocalypse version of his Negan character from The Walking Dead.

  • 63/ Fox Atomic

    #39. Post Grad

    Stacker Score: 30.50

    IMDb rating: 5.3

    Tomatometer: 8%

    Before his late career resurgence was sparked by 2014’s Birdman, Michael Keaton played the father to a recent college grad (Alexis Bledel of Gilmore Girls) in this middling 2009 comedy about a girl finding her feet in the wider world beyond college. Critics found the script schlocky, the stakes sitcom-level low and the love story predictable. Audiences barely registered the movie, which brought in $6.37M.

  • 64/ DreamWorks

    #38. Surviving Christmas

    Stacker Score: 30.50

    IMDb rating: 5.4

    Tomatometer: 7%

    In a plot that calls for way too much suspension of disbelief from the outset, a wealthy but alienated ad exec (Ben Affleck) bribes a family (with a dad played by James Gandolfini) to pose as his own so that he doesn’t have to spend Christmas alone. The story pivots when the family’s eldest daughter (Christina Applegate) arrives late and throws a new romantic wrench into his fantasy. Predictable and humorless complications ensue. Amazingly, the WGA lists four screenwriters for this trainwreck. An $11.66M box office made for a disappointing holiday haul.

  • 65/ Universal Pictures

    #37. The Perfect Man

    Stacker Score: 30.50

    IMDb rating: 5.5

    Tomatometer: 6%

    This is a movie about catfishing that predates the term entering the cultural lexicon. Holly (Hilary Duff) is sick of dealing with the fallout of her mother’s failed relationships, so she creates a fictional online persona to court her mom in the hopes it will raise her mom’s standards in men. When her mother (Heather Locklear) becomes invested in the romance, Holly must produce a real man to fill the shoes of the virtual suitor she’s created. Critics rolled their eyes at the overly sentimental dialogue and obvious pandering to the tween crowd. The picture grossed a disappointing $16.25M.

  • 66/ Universal Pictures

    #36. Howard the Duck

    Stacker Score: 30.50

    IMDb rating: 4.6

    Tomatometer: 15%

    Adapted from a comic book, Lucasfilm’s worst ever flop ($16.3M) blends the superhero and comedy genres with a central love subplot between an anthropomorphic duck (who finds himself stranded on Earth) and a wannabe singer (Lea Thompson). Hardcore fans of the comic were disappointed at the cutesy portrayal of Howard (who is far cruder and edgier in the original material), while mainstream audiences found the duck/girl romance creepy. The Howard costume, cheap-looking and expressionless, creates an off-putting uncanny valley effect that further adds to the discomfort of watching this movie. Nevertheless, the movie and the character it was based on have become (perhaps ironic) cult classics. Recently, a CGI version of Howard the Duck made cameos in both Guardians of the Galaxy movies.

  • 67/ Lionsgate

    #35. Good Luck Chuck

    Stacker Score: 30.50

    IMDb rating: 5.6

    Tomatometer: 5%

    This film gave a lot of ammunition to members of the “Dane Cook isn’t funny” bandwagon. The premise is actually chuckle-worthy: A serial dater who was hexed by a goth girl into perpetual singledom as a 10-year-old must try to make an adult relationship with a sexy penguin specialist work. Unfortunately, due to the lack of comedic chops in the cast—Cook aside, could they have picked anyone less amusing than Jessica Alba to co-star?—the movie was slammed by critics and by countless road comics who, jealous of Cook’s stardom, slagged it off in clubs around the country. Cook’s fan base showed up anyway, and the film raked in $34.93M to turn a profit.

  • 68/ Warner Bros.

    #34. New York Minute

    Stacker Score: 30.00

    IMDb rating: 4.9

    Tomatometer: 11%

    This 2004 movie was supposed to be the Olsen twins’ big leap from child actors to teen stars, but it was a misfire on all cylinders. The Olsens play a pair of sisters with a conflicted relationship who spend a wild 24 hours in Manhattan while being pursued by a truant officer (Eugene Levy). Dr. Drew Pinsky of the radio show Loveline and all those Celebrity Rehab shows makes his hilariously wooden big-screen debut as the girls’ father. For all their experience in front of the camera, the Olsens never seemed to have picked up any acting chops, and critics were not kind to the performances in the film. Or to the script. Or the direction. Or to anything about it at all, really. Tweens (and perhaps the occasional shady character in a trenchcoat) shelled out $14.02M in theaters.

  • 69/ Paramount Pictures

    #33. Yours, Mine & Ours

    Stacker Score: 30.00

    IMDb rating: 5.4

    Tomatometer: 6%

    Hacky director Raja Gosnell, who went on to make the Smurfs movies, figured he could improve on Cheaper By The Dozen by adding more kids. What he didn’t figure is that child actors are, by and large, excruciatingly annoying. Dennis Quaid and Rene Russo play the newlywed parents forced to wrangle the overblown brood of 18. Critics found it shrill and disposable, but audiences starved for family-friendly options shelled out $53.41M to bring their own brats out to see it.

  • 70/ Eclectic Pictures

    #32. Playing for Keeps

    Stacker Score: 30.00

    IMDb rating: 5.7

    Tomatometer: 3%

    Not to be mistaken for the 1986 rock & roll flick of the same name (written and directed by the Weinstein brothers before they became mega-producers), this lame 2012 romcom sees Gerard Butler playing a former soccer star who, in coaching his son’s team, must fend off constant romantic advances from soccer moms. Jessica Biel, Uma Thurman and Catherine Zeta-Jones are entirely wasted on an uninspired script that doesn’t bother to flesh out its female characters as anything other than potential conquests. Even with its star-studded cast, it only managed a $13.1M haul.

  • 71/ Columbia Pictures

    #31. Did You Hear About the Morgans?

    Stacker Score: 30.00

    IMDb rating: 4.8

    Tomatometer: 12%

    A Manhattan alpha couple gets a second chance to repair their flailing marriage when they’re relocated to a tiny town in Wyoming through witness relocation. (Yes, it’s a plot that sounds like the kind of movie you might see parodied in a Judd Apatow comedy.) Critics acknowledged moments of onscreen charm between leads Hugh Grant and Sarah Jessica Parker, but overall consensus was that the movie was cynical studio dreck. The domestic gross of $29.58M was nothing to write home about, but the film performed well overseas and brought in a total of $85.3M internationally.

  • 72/ Universal Pictures

    #30. Because I Said So

    Stacker Score: 30.00

    IMDb rating: 5.6

    Tomatometer: 4%

    Diane Keaton, in what film critic Richard Roeper singled out as the worst performance of her career, plays a meddlesome mother intent on setting her daughter (Mandy Moore) up with Mr. Right. Panned as a cliché, sappy, superficial chick flick, the film was dumped in the typically undesirable early February release window of 2007. Even so, ticket sales around Valentine’s Day were strong enough that the movie was marginally profitable, raking in $42.67M domestically. In retrospect, it’s difficult to know who to pity more, the lonely hearts who saw this one solo or the significant others who were dragged out for date night.

  • 73/ Warner Bros.

    #29. License to Wed

    Stacker Score: 30.00

    IMDb rating: 5.3

    Tomatometer: 7%

    A reverend (Robin Williams) puts an engaged couple through the ringer in his grueling marriage preparation course. John Krasinski of the American version of The Office plays the aspiring groom alongside Mandy Moore as his would-be bride. Williams’ performance was phoned in, and the script is predictable and unfunny. The domestic gross of $43.8M is a career high for Moore as an actress on the silver screen, just edging out the box office performance of the next movie on this list...

  • 74/ Double Feature Films

    #28. LOL

    Stacker Score: 30.00

    IMDb rating: 4.3

    Tomatometer: 17%

    Few people saw LOL in its limited U.S. release, and fewer had anything positive to say about it. Miley Cyrus stars as high schooler Lola (“Lol” to her pals) who falls for her best friend, a musician played by Douglas Booth. The film’s promotional materials emphasized its digital hipness, but forcing social media and text message terminology into the characters’ dialogue hardly elevates the standard high school romance formula to new heights. Demi Moore, playing the mother character, adds another black mark to her checkered late-career resume.

  • 75/ New Line Cinema

    #27. Sex and the City 2

    Stacker Score: 30.00

    IMDb rating: 4.4

    Tomatometer: 16%

    The critics who were lukewarm on the first big-screen adaptation of the hit HBO show really sank their teeth into its sequel. And at a running time of almost 2.5 hours, the film served up plenty of fodder for their criticisms. Most reviewers agreed that Carrie (Sarah Jessica Parker) and her crew of Manolo-heeled NYC gal pals had long overstayed their welcome and warned that only diehard fans need consider lining up for this pointless and thinly plotted coda to their saga. It still made a boatload—$95.35M—but by this point, the loft salary requirements of its stars had produced a budget that exceeded its return.

  • 76/ Twentieth Century Fox

    #26. Say It Isn't So

    Stacker Score: 29.00

    IMDb rating: 4.9

    Tomatometer: 9%

    The Farrelly Brothers produced this 2001 romantic comedy, directed by J.B. Rogers, who had previously worked with them as a first assistant director. Gilly (Chris Klein) and Jo (Heather Graham) are enjoying a passionate love affair when they find out they’re actually brother and sister and have to break things off in a hurry. But when he finds out their supposed blood-relation is in fact a lie perpetuated by a meddling third party, Gilly must rush to stop Jo’s marriage to “the wrong guy.” The incest humor creeped out critics and audiences, and overall, the movie lacked the charm, humor and originality of the Farrelly’s earlier sleeper hit There’s Something About Mary. The box office total was $5.52 million.

  • 77/ Warner Bros.

    #25. Summer Catch

    Stacker Score: 29.00

    IMDb rating: 5.0

    Tomatometer: 8%

    Another Freddie Prinze Jr. romcom, this time pairing the actor up with Jessica Biel. The story, a classic Lady and the Tramp setup, has Prinze Jr.’s blue-collar baseball player character falling for an unattainable upper-crust girl with a controlling father. The critics’ consensus was that there wasn’t enough baseball for a baseball movie and that the romance lacked sufficient flavor or complication to draw interest. Box office receipts were a just below $20M.

  • 78/ Regency Enterprises

    #24. First Daughter

    Stacker Score: 29.00

    IMDb rating: 5.0

    Tomatometer: 8%

    The daughter of the President of the United States (Katie Holmes) falls in love with her college RA who, unbeknownst to her, is really an undercover secret service agent tasked with her protection. Critics made unfavorable comparisons to the conceptually similar (but slightly less awful) Chasing Liberty from the same year and declared the picture too saccharine for viewers outside the tween girl demo. The movie grossed $9.06M.

  • 79/ FTM Productions

    #23. Serving Sara

    Stacker Score: 28.50

    IMDb rating: 5.3

    Tomatometer: 4%

    Joe, played by Matthew Perry, gets more than he bargained for when he’s tasked with serving divorce papers to the elusive Sara, played by Elizabeth Hurley. The typical romantic comedy plot plays out, and opposites end up attracting without much regard for originality or humor. As bland as this movie is, the offscreen events surrounding its production made for juicy tabloid fodder. Perry landed in rehab for painkiller addiction during production, and later Hurley’s boyfriend accused Perry of impregnating her (a claim was later discredited through blood tests). If only the script had been as intriguing.

     

  • 80/ Revolution Studios

    #22. Are We There Yet?

    Stacker Score: 28.50

    IMDb rating: 4.6

    Tomatometer: 11%

    This 2005 movie made a good bundle—$82.67M—but flopped with reviewers. Ice Cube is forced to take a long road trip with the bratty kids of his new girlfriend (Nia Long), who resent any man besides their father putting the moves on mom. Critics piled onto Cube for selling out his edgy NWA persona in favor of family pap, and many found the kids’ performances too unlikeable to stomach. Nevertheless, a 2007 sequel saw the cast reuniting for another cash grab.

  • 81/ Warner Bros.

    #21. Arthur 2: On the Rocks

    Stacker Score: 28.00

    IMDb rating: 4.3

    Tomatometer: 13%

    This much maligned sequel saw a sharp drop-off in quality from the beloved 1981 original. Dudley Moore and Liza Minnelli return as the romantic leads, and this time the story focuses on the rocky aftermath of their marriage at the end of the first movie. But the characters hadn’t aged well since their debut 7 years prior, and critics rejected the picture. Many commented on the dated treatment of alcoholism as cheerily humorous subject matter as being particularly out of touch. An attempt to reboot the character in 2011, with real-life recovering addict Russell Brand starring, didn’t fare much better critically or commercially.

  • 82/ Morgan Creek Entertainment

    #20. Juwanna Mann

    Stacker Score: 27.50

    IMDb rating: 4.5

    Tomatometer: 10%

    An urban spin on a Tootsie-style gender-switch plot, Juwanna Mann stars longtime character actor Miguel A. Núñez in his first and last leading role. The story’s about a hot-tempered basketball player who gets booted from the league and decides to don some fake breasts and eyelashes to try his luck on the women’s side of the game. He lands a spot on a team, but his plan gets thrown into turmoil when he starts to fall for a no-nonsense coach, played by Vivica A. Fox. Critics found it simplistic and unoriginal, and its $13.57M box office haul didn’t cover its production budget. Nevertheless, in a 2015 TMZ interview, Núñez claimed a Juwanna Mann sequel was in the works, although as of now, IMDb provides no corroboration for this claim.  

  • 83/ Universal Pictures

    #19. Dudley Do-Right

    Stacker Score: 27.50

    IMDb rating: 3.9

    Tomatometer: 16%

    This 1999 movie was adapted from "Dudley Do-Right of the Mounties," a segment on The Rocky and Bullwinkle Show. Brendan Fraser, who two years prior had hit commercial paydirt with the adaptation of another Saturday Morning cartoon, George of the Jungle, starred. His co-star Sarah Jessica Parker played the daughter of Dudley’s superior and served as the love interest. The plot revolves around the bamboozling of their town, high up in the Canadian Rockies, by Snidely Whiplash, an outside huckster whom Dudley is too inept to stop, until (through the magic of a convenient character arc) he isn’t. The slapstick humor was too juvenile for most critics. Parents looking for a flick to keep the kiddies engaged shelled out $9.69M at the box office, a far yodel from George of the Jungle’s gargantuan $174.4M.

  • 84/ Eddie Murphy Productions

    #18. Vampire in Brooklyn

    Stacker Score: 27.50

    IMDb rating: 4.5

    Tomatometer: 10%

    Comedy-horror rarely works as a mashup. For every American Werewolf in London, there are dozens of misfires that fail to balance the competing requirements of the two genres. This is one of those. Eddie Murphy plays a vampire named Maximillian, who tries to seduce a detective while sabotaging the romantic advances of her longtime partner. Horror veteran Wes Craven directed, but failed to provide any real scares. Critic Roger Ebert wrote of the film: “To call this a comedy is a sign of optimism; to call it a comeback for Murphy is a sign of blind faith.” Audiences were at least curious enough that the film pulled in a haul just shy of $20M, but it was poorly regarded and has not stood the test of time.

  • 85/ Fox Atomic

    #17. Miss March

    Stacker Score: 27.50

    IMDb rating: 5.0

    Tomatometer: 5%

    A high-schooler (Zach Cregger) falls into a coma on the eve of losing his virginity to his high school sweetheart (Raquel Alessi). When he wakes up four years later, he discovers she’s gone on to a glamorous life as a Playboy centerfold. The premise might have worked if there was any subtlety to the execution, but this is another movie on this list that aims for scatalogical humor over character-driven comedy. The obligatory Hugh Hefner cameo wasn’t enough to draw in audiences, and this flop didn’t even manage to clear $5M at the box office.

  • 86/ Metro-Goldwyn-Mayer (MGM)

    #16. Van Wilder 2: The Rise of Taj

    Stacker Score: 27.50

    IMDb rating: 4.8

    Tomatometer: 7%

    There’s considerable ambiguity over what constitutes a National Lampoon movie. The National Lampoon comedy magazine first began spinning off its articles into movies in 1978, but over the years (particularly following the success of Animal House), they began licensing out their name to various projects. They finally outright sold the rights to apply their brand to movies in 2002. This brings us to 2006’s Van Wilder 2: The Rise of Taj, which falls well outside the National Lampoon golden years and marks a low point in the brand’s slide from comedic trailblazing to lowest-common-denominator frat boy humor. Kal Penn, who played a protégé to Ryan Reynolds’ Van Wilder character in the original, reprises his role in this sequel, which takes him over the pond to England to party with the students at fictional Camford University. This one’s barely a romantic comedy—more of a party movie with a romantic subplot—but the few scenes with love interest Charlotte (Lauren Cohan, who went on to play Maggie on The Walking Dead) are so tone-deaf and unrealistic due to the “she’s out of his league” factor, they warrant inclusion. Critics hated the sophomoric humor and Ryan Reynolds’ refusal to return even for a cameo kept audiences from showing up. The film’s $6M gross was a fraction of the original’s $38.3M.

  • 87/ Dimension Films

    #15. My Boss's Daughter

    Stacker Score: 27.50

    IMDb rating: 4.7

    Tomatometer: 8%

    Ashton Kutcher plays a rookie executive who agrees to house-sit for his boss in the hopes of spending time with the man’s attractive daughter (Tara Reid). Reviews declared the script crude and offensive and the film received three Razzie Award nominations including Worst Actor (Ashton Kutcher), Worst Supporting Actress (Tara Reid) and Worst Screen Couple. The movie still managed to gross over $15M, enough to cover its production budget and then some.

  • 88/ Fox 2000 Pictures

    #14. All About Steve

    Stacker Score: 27.50

    IMDb rating: 4.8

    Tomatometer: 7%

    Sandra Bullock plays against type in this quirky comedy about a kooky puzzle maker who begins stalking a cameraman played by Bradley Cooper. The usually charming Bullock delivers a performance creepier than was perhaps intended, and critics lambasted the film for its odd, offputting tone and unlikeable heroin. Nevertheless, the star power of the cast attracted a large enough audience that the film grossed over $40M, more than doubling its production budget.

  • 89/ Lakeshore Entertainment

    #13. One for the Money

    Stacker Score: 27.50

    IMDb rating: 5.3

    Tomatometer: 2%

    Katherine Heigl stars as Stephanie Plum, a neophyte bail bond recovery agent who’s tasked with nabbing a bail-jumper who just so happens to be the guy who broke her heart back in high school. The story was adapted from the first in a long-running series of Stephanie Plum novels, but the translation to the screen was ill-fated. Too many familiar, paint-by-numbers plot elements kept the critics’ thumbs pointed firmly down, although the movie did manage to haul in $36.9M at the box office, making back most of its budget.

  • 90/ Hawaii Film Partners

    #12. You May Not Kiss the Bride

    Stacker Score: 27.00

    IMDb rating: 5.4

    Tomatometer: 0%

    Sitting at an impressive 0% on the tomatometer, this movie did no favors for leads Dave Annable and Katharine McPhee. The plot kicks off with an unassuming guy marrying the daughter of a Croatian mobster. It then takes a left turn when the new bride is kidnapped on their honeymoon in Tahiti. Critics weren’t willing to go along with the incongruous plot elements and silly writing. Apparently the studio had their reservations about the picture too—despite shooting in 2009, its release was delayed until the spring of 2012, when it came and went without much fanfare.

  • 91/ Millennium Films

    #11. Blonde Ambition

    Stacker Score: 26.50

    IMDb rating: 3.9

    Tomatometer: 14%

    Basically a Legally Blonde ripoff set in the business world, this film has Jessica Simpson climbing the corporate ladder while juggling romance along the way. The film isn’t as glaringly awful as some of the others on this list, just eminently forgettable. It made back just over half its $19M budget in theaters, though for some reason it was a big hit in Ukraine, where it debuted at No. 1 in its opening weekend.

  • 92/ Wayanz Alvarez Productions

    #10. Naked

    Stacker Score: 26.50

    IMDb rating: 5.3

    Tomatometer: 0%

    A Netflix original production, this film borrows the central plot device from Groundhog Day and has Marlon Wayans reliving the nerve-wracking stretch of time before his wedding day over and over again. Critics found it unrealistic, unoriginal and unfunny. Netflix released it with barely any marketing campaign in the dog days of summer, minimizing audience exposure.

  • 93/ Open City Films

    #9. Down to You

    Stacker Score: 26.00

    IMDb rating: 4.9

    Tomatometer: 3%

    In an attempt at a teen version of Annie Hall, this movie starred then-faves Freddie Prinze Jr. and Julia Stiles as a pair of 19-year olds struggling to navigate the trials and tribulations of young love in the Big Apple. An aimless story, adolescent dialogue and lack of onscreen romantic chemistry drew a tepid response from critics, and the movie lost money for Miramax.

  • 94/ Paramount Pictures

    #8. The Love Guru

    Stacker Score: 25.50

    IMDb rating: 3.8

    Tomatometer: 13%

    Prior to helming this Mike Myers flop, director Marco Schnabel’s career was in dire straits. After being fired early on during the making of the Will Ferrell soccer comedy Kicking and Screaming, Schnabel was having a hard time convincing any studio executive to let him make another movie. So when he was tapped by Myers, who knew him from his second unit director stint on Goldmember, he leapt at the opportunity to get back behind the camera. Unfortunately Myers’ new character, a hippyish love guru tasked with healing the marriage of a hockey player, failed to resonate with audiences as Austin Powers had. The movie—cheesy, juvenile and grating—fell $20M shy of recouping its budget. It remains Schnabel’s sole IMDb credit as a director.

  • 95/ K. JAM Media

    #7. Accidental Love

    Stacker Score: 25.00

    IMDb rating: 4.1

    Tomatometer: 9%

    This is a weird one. The story’s about Alice, a soon-to-be-wed waitress (played by Jessica Biel) who, through a freak accident, ends up with a nail lodged in her head. The injury produces bizarre and hypersexual behavior that leads to Alice’s fiance calling off their marriage. She rebounds into the arms of a senator (Jake Gyllenhaal) who helps empower her campaign for people with bizarre injuries. The film was directed and co-written by five-time oscar nominee David O. Russell, who was so ashamed of his work on the flick that he abandoned it in its final stages and opted to be credited with a pseudonym. His instincts were on the money. The movie, which never opened beyond a limited release, recouped only $4,500 of its $26M budget and was panned by critics for its crudeness and messy, unsatisfying storytelling.

  • 96/ DreamWorks

    #6. Norbit

    Stacker Score: 24.50

    IMDb rating: 4.0

    Tomatometer: 9%

    Eddie Murphy had an epic run of bad movies in the 2000s, and Norbit is perhaps the worst of the bunch. The conflict of the story centers on the title character trying to flee a bad marriage for greener romantic pastures. But his path to freedom requires standing up to his abusive, obnoxious, morbidly obese spouse, also played by Murphy. As if the offensive fat-suit humor wasn’t enough tastelessness for one film, Eddie also managed to jam in some cringeworthy racial humor in his third performance in the film as Mr. Wong, a walking Asian stereotype who displays blatant prejudice throughout the film.  Norbit grossed over $95 million domestically, proving there’s no accounting for (bad) taste.

  • 97/ Big Screen Entertainment Group

    #5. Dirty Love

    Stacker Score: 19.50

    IMDb rating: 3.5

    Tomatometer: 4%

    Jenny McCarthy wrote and starred in this miscalculated story of a girl who tries to reenter the dating world after a messy breakup. While some critics found McCarthy’s onscreen presence charming, they were less impressed with her screenwriting abilities, particularly in the comedy department. Her then-husband John Asher directed the picture, and it’s perhaps no coincidence that the couple divorced the month it was released. Critically panned and a bomb at the box office, this movie failed on all counts.

  • 98/ New Regency Pictures

    #4. Date Movie

    Stacker Score: 17.50

    IMDb rating: 2.8

    Tomatometer: 7%

    When the best blurb you can come up with for your movie poster is “from 2 of the 6 writers of Scary Movie,” you know you’ve got a real gem on your hands. An extremely broad comedy that fails to be funnier than the movies it parodies, Date Movie focuses on the build-up to a wedding between a formerly-obese bride (Alyson Hannigan) and a (supposedly) charming Englishman (Adam Campbell). The movie grossed a respectable $48.55 million, but its poor critical reception pretty much ended any hopes Hannigan might have had for a movie career beyond the American Pie franchise.

  • 99/ 19 Entertainment

    #3. From Justin to Kelly

    Stacker Score: 15.50

    IMDb rating: 2.1

    Tomatometer: 10%

    When the best blurb you can come up with for your movie poster is “from 2 of the 6 writers of Scary Movie,” you know you’ve got a real gem on your hands. An extremely broad comedy that fails to be funnier than the movies it parodies, Date Movie focuses on the build-up to a wedding between a formerly-obese bride (Alyson Hannigan) and a (supposedly) charming Englishman (Adam Campbell). The movie grossed a respectable $48.55 million, but its poor critical reception pretty much ended any hopes Hannigan might have had for a movie career beyond the American Pie franchise.

  • 100/ Revolution Studios

    #2. Gigli

    Stacker Score: 15.00

    IMDb rating: 2.4

    Tomatometer: 6%

    One of the worst commercial flops in history, Gigli made back less than a 10th of its $75 million budget. The story follows a romance that develops between two kidnappers, and it was derided as bizarre and poorly paced by critics. The lack of onscreen chemistry between stars Ben Affleck and Jennifer Lopez—who, during filming, were involved in the highly publicized “Bennifer” romance—made for easy fodder for late-night comedians. Ben Affleck has acknowledged the badness of the film in several interviews.

  • 101/ Purple Pictures

    #1. The Hottie & the Nottie

    Stacker Score: 12.00

    IMDb rating: 1.9

    Tomatometer: 5%

    This 2008 Paris Hilton vehicle was a commercial and critical misfire, grossing less than $30K domestically. The plot centers on Paris Hilton, the titular “hottie,” sexually blackmailing a potential suitor into finding a boyfriend for her homely best friend. Critics eviscerated the film for its overreliance on gross-out humor and shallow subject matter, and in 2010, Paris’ wooden performance helped her to clinch the “worst actress of the decade” win at the 30th annual Razzie Awards.

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