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Top 100 country songs of all time

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Rick Diamond/Getty Images for Country Music Hall of Fame & Museum

Top 100 country songs of all time

The 53rd Annual Country Music Association Awards, airing live from Nashville on Nov. 13, 2019, will be hosted by Carrie Underwood with guest hosts Reba McEntire and Dolly Parton. Throughout the broadcast, viewers will see performances by Kacey Musgraves with Willie Nelson, Brooks & Dunn with Brothers Osborne, Garth Brooks with Blake Shelton, Dan + Shay, Eric Church, Luke Combs, Lady Antebellum and Halsey, Miranda Lambert, Keith Urban, Blake Shelton, Thomas Rhett, P!nk and Chris Stapleton, Old Dominion, Maren Morris, and Kelsea Ballerini—as well as performances from the hosts, Underwood, McEntire, and Parton (with for King & Country and Zach Williams). 

In anticipation of this star-studded night of music and memorable performances, it's time to look back at the best country anthems of all time.

Stacker analyzed Billboard’s Greatest of All-Time Top Country Songs to create a ranked list of classic tracks and modern hits from 1959 to present day. This list is remarkably varied, proving country music as a genre is broader than some may believe; it also shows how the genre has grown to feature a redefined picture of a classic country superstar, from Johnny Cash, Dolly Parton, and Willie Nelson to Faith Hill, Taylor Swift, Sam Hunt, and Kacey Musgraves. Some even say the sound of country music has changed: Younger subgenres of country music include bro-country (Sam Hunt, Florida Georgia Line), stadium country (Garth Brooks, Keith Urban), and pop country (Taylor Swift)—and some artists are even experimenting with country rap (Bubba Sparxxx, Colt Ford). 

From classic country tunes to contemporary country sounds, these 100 songs are an essential part of music history and showcase some of the most impressive storytelling skills in the genre. Read on to see if your favorite country hit made it to the top.

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Bob Jagendorf // Wikimedia Commons

#100. 'Good Hearted Woman' by Waylon & Willie

- Artist: Waylon Jennings and Willie Nelson
- Billboard rank: #100

Jennings convinced Nelson to record the soon-to-be iconic song during a poker game in 1971, inspired by an advertisement for Ike and Tina Turner. It won a CMA for Single of the Year and helped form the two artists' outlaw image.

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RCA Records // Wikimedia Commons

#99. 'This Is It' by Jim Reeves

- Artist: Jim Reeves
- Billboard rank: #99

Jim Reeves died in an airplane accident in 1964, though his records made the charts from the 1950s to the 1980s. Reeves, also known as "Gentleman Jim," was more popular in South Africa than Elvis Presley, and recorded several albums in the Afrikaans language. "This Is It" made waves as a heartfelt breakup anthem.

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Columbia Records // Wikimedia Commons

#98. 'Thinkin' Of A Rendezvous' by Johnny Duncan

- Artist: Johnny Duncan
- Billboard rank: #98

Johnny Duncan’s first-ever #1 single on the Billboard Country Chart spent 13 weeks in the top 40. The 1976 hit told the tale of a family man who meets up with a longtime friend he's had an affair with.

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Vince Bucci // Getty Images

#97. 'High Cotton' by Alabama

- Artist: Alabama
- Billboard rank: #97

One of four songs in the album to reach the top of the country charts, “High Cotton” held the title the longest. The narrator reminisces about the good old days and bemoans life's unexpected changes.

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Bede735 // Wikimedia Commons

#96. 'You Look So Good In Love' by George Strait

- Artist: George Strait
- Billboard rank: #96

Though George Strait is one of the biggest names in country music, this 1983 recording was his first hit song in many years. In the song, the narrator gloomily realizes that his former girlfriend is now in love, and he comes to terms with the fact it wasn’t meant to be.

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Carlo Allegria // Getty Images

#95. 'Breathe' by Faith Hill

- Artist: Faith Hill
- Billboard rank: #95

Though the song peaked at #2 on the Billboard Hot 100, "Breathe" was still declared the top single of 2000—the first time that's occurred in 35 years. In this romantic tune, Faith Hill showers her significant other, presumably husband Tim McGraw, with sweet nothings.

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Rusty Russell // Getty Images

#94. 'Why Not Me' by The Judds

- Artist: The Judds
- Billboard rank: #94

The red-headed family duo lament their relationships—this time, he’s not giving them the attention they crave. The 1984 single also hit #1 on the country charts.

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Rusty Russell // Getty Images

#93. 'Mind Your Own Business' by Hank Williams Jr.

- Artist: Hank Williams Jr.
- Billboard rank: #93

The singer's father, Hank Williams, originally recorded this song in 1949. The song, which the original artist called a “prophecy,” has been covered over and over, frequently appearing on the country charts. Hank Williams Jr. released his rendition in 1986.

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Rick Diamond // Getty Images

#92. 'Cry Myself To Sleep' by The Judds

- Artist: The Judds
- Billboard rank: #92

Wynonna and Naomi Judd’s condemnation of a misbehaving man was the mother-daughter duo's eighth #1 country hit. The 1986 recording follows a women’s intent to stay with her partner at any cost.

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Pxhere

#91. 'If You Leave Me Tonight I'll Cry' by Jerry Wallace

- Artist: Jerry Wallace
- Billboard rank: #91

“If You Leave Me Tonight I'll Cry” was Wallace’s only chart-topping hit. The heartbreaking 1972 recording described the end of a relationship, and was popularized in the hit horror show “Night Gallery.”

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Jeff Gross // Getty Images

#90. 'Killin' Time' by Clint Black

- Artist: Clint Black
- Billboard rank: #90

In 1989, Billboard declared “Killin’ Time” the #2 country song of the year—defeated only by another Clint Black song. Throughout the recording, the narrator complains that he’s wasting his life away drinking in hopes of forgetting a former lover.

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Kathy Hutchins // Shutterstock

#89. 'Girl Crush' by Little Big Town

- Artist: Little Big Town
- Billboard rank: #89

This 2014 hit left critics and audiences confused. What is this song about: having a crush on a woman, or a desire to take over her life to win back the man she stole? The emotionally charged recording hit #1 on the country charts.

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Eva Rinaldi // Wikimedia Commons

#88. 'Our Song' by Taylor Swift

- Artist: Taylor Swift
- Billboard rank: #88

The pop princess’ first massive hit was “Our Song,” which was originally written to be performed at a high school talent show. The artist’s musings about a relationship without a song became a universal hit in 2007, spending 36 weeks on the Billboard Hot 100.

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Michael Buckner // Getty Images

#87. 'Just Got Started Lovin' You' by James Otto

- Artist: James Otto
- Billboard rank: #87

James Otto’s deep vocals have been compared to those of country legend Conway Twitty. His voice was so highly regarded that songwriter Jim Femino personally arranged a meeting to get him in the studio.

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Rick Diamond // Getty Images

#86. 'Pickup Man' by Joe Diffie

- Artist: Joe Diffie
- Billboard rank: #86

In his 1994 ballad, Joe Diffie jokes throughout the course of the song he'll win over the girl of his dreams by driving a pickup truck. The jovial song resonated with audiences and became his longest-lasting #1 hit on the Billboard country charts.

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Shanecollinswiki // Wikimedia Commons

#85. 'I Fall To Pieces' by Patsy Cline and Jim Reeves

- Artist: Patsy Cline and Jim Reeves
- Billboard rank: #85

This 1961 single is a country standard. Radio stations ignored the song altogether at first, but Patsy Cline’s hit crossed over to the pop charts and hit #1.

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Greg Mathison // Wikimedia Commons

#84. '(I'm So) Afraid Of Losing You Again' by Charley Pride

- Artist: Charley Pride
- Billboard rank: #84

Charley Pride had several hits in his day. In this song, the narrator expresses his fear of losing the love of his life.

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Epic Records // Wikimedia Commons

#83. 'Baby, Baby (I Know You're A Lady)' by David Houston

- Artist: David Houston
- Billboard rank: #83

This 1969 song was the first hit by up-and-coming songwriter Norro Wilson, who went on to write songs for dozens of country music’s most prolific chart-toppers. In this recording, the narrator begs a woman to let him declare his love for her.

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Rick Diamond // Getty Images

#82. 'Lost In The Fifties Tonight (In The Still Of The Night)' by Ronnie Milsap

- Artist: Ronnie Milsap
- Billboard rank: #82

The 1985 single blends a new recording with a cover of the 1956 hit, "In the Still of the Night.” It was Milsap’s 42nd single, 27th #1 hit on the country charts, and first Grammy-winning recording.

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Frederick M. Brown // Getty Images

#81. 'My Heart Skips A Beat' by Buck Owens

- Artist: Buck Owens
- Billboard rank: #81

“My Heart Skips A Beat” was Buck Owens’ third #1 country hit during a long reign over the charts. The tune is one of several on this list that takes an upbeat approach to relationships.

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Frederick Breedon // Getty Images

#80. 'God Gave Me You' by Blake Shelton

- Artist: Blake Shelton
- Billboard rank: #80

Though the song was originally recorded by a Christian artist, Blake Shelton’s 2011 cover brought it into the spotlight. Critics didn’t love Shelton's performance, but it nevertheless earned the country legend his fifth consecutive #1 single.

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Epic Records // Wikimedia Commons

#79. 'There Won't Be Anymore' by Charlie Rich

- Artist: Charlie Rich
- Billboard rank: #79

This song was recorded in the 1960s, but it wasn’t released as a single until 1973. The pop crossover, which features a saxophone solo, is an anthem of closure for a broken relationship.

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Disney ABC Television Group // Flickr

#78. 'Die A Happy Man' by Thomas Rhett

- Artist: Thomas Rhett
- Billboard rank: #78

Thomas Rhett’s sweet 2015 song topped multiple charts and was a popular choice for first dances at weddings. The music video features Rhett's wife, and the song received plenty of of pop airplay when producers added vocals from artist Tori Kelly.

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MCA Records // Wikimedia Commons

#77. 'My Heart/Silent Night (After The Fight)' by Ronnie Milsap

- Artist: Ronnie Milsap
- Billboard rank: #77

The 1980 medley is a combination of two hit songs. The first starts with a narrator realizing he wronged someone, and the second ends when he discovers nothing can be done about it. 

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Capitol Records // Wikimedia Commons

#76. 'If We Make It Through December' by Merle Haggard

- Artist: Merle Haggard
- Billboard rank: #76

Merle Haggard’s 1971 single, with lyrics referencing unemployment and loneliness, also bears a holiday theme. Critics enjoyed the song, attesting it contributed to Haggard's reputation as a “complete artist.”

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Camera-Craft, Seattle // Wikimedia Commons

#75. 'Before You Go' by Buck Owens

- Artist: Buck Owens
- Billboard rank: #75

The title track of Buck Owens’ 1965 album was his seventh to hit #1 on the Billboard country singles chart. In the soulful song, the narrator begs his lover to remember that he loves her before she leaves, following an argument.

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Rick Diamond // Getty Images

#74. 'Two Dozen Roses' by Shenandoah

- Artist: Shenandoah
- Billboard rank: #74

In this melancholy song, a narrator desperately wants to know what he could have done to stop his lover from leaving, eventually realizing it’s out of his hands. The 1989 recording hit #1 on the country charts, and left fans with several infamous breakup lines.

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Stephen Lovekin // Getty Images

#73. 'It's Just A Matter Of Time' by Randy Travis

- Artist: Randy Travis
- Billboard rank: #73

Though the song was originally recorded as a pop performance, three country artists covered it. Randy Travis found the most success with this tune, hitting #1 on the country charts in 1989.

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Rick Diamond // Getty Images

#72. 'Good Morning Beautiful' by Steve Holy

- Artist: Steve Holy
- Billboard rank: #72

Steve Holy’s hit was originally released as part of the soundtrack for the movie “Angel Eyes.” It’s an upbeat song with no twist ending: only happiness and hope between two lovers.

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Country Music Association // Wikimedia Commons

#71. 'Big City' by Merle Haggard

- Artist: Merle Haggard
- Billboard rank: #71

This 1982 single was Merle Haggard’s 27th #1 hit on the country charts, cementing him as one of the most popular country artists in history. A friend's complaints inspired many of the lyrics that lamented life in a big, dirty city.

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Rick Diamond // Getty Images

#70. 'Black Sheep' by John Anderson

- Artist: John Anderson
- Billboard rank: #70

This 1983 song, which describes the narrator's rejection of societal expectations, propelled John Anderson to the top of the country charts for the third time. "Black Sheep" spent 14 weeks in the top 40.

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Frazer Harrison // Getty Images

#69. 'Lookin' For Love' by Johnny Lee

- Artist: Johnny Lee
- Billboard rank: #69

“Lookin’ For Love” is the second song on this list that was originally released as part of a soundtrack, this time for “Urban Cowboy.” The song had reportedly been pitched to more than 20 artists before finding a home with Johnny Lee. It took off when John Travolta, star of “Urban Cowboy,” said he enjoyed it.

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Rick Diamond // Getty Images

#68. 'Love, Me' by Collin Raye

- Artist: Collin Raye
- Billboard rank: #68

This 1991 single was Raye’s first #1. The tragic, but inspirational ballad earned a “Single of the Year” nomination at that year's CMAs, and is commonly played at funerals.

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Kevin Winter // Getty Images

#67. 'Don't Rock The Jukebox' by Alan Jackson

- Artist: Alan Jackson
- Billboard rank: #67

When this song was released in 1991, Alan Jackson was not nearly the country powerhouse he would later become—but the single raced to the top of the charts regardless. The honky-tonk anthem was later covered by Alvin and the Chipmunks.

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Pierre Gui // Unsplash

#66. 'Giddyup Go' by Red Sovine

- Artist: Red Sovine
- Billboard rank: #66

“Giddyup Go” is a country song about driving a truck, following the story of a father and son who have an emotional reunion at a truck stop. It's famous for its surprise ending that country songs often have.

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Pixabay

#65. 'Don't Let Me Cross Over' by Carl Butler and Pearl

- Artist: Carl Butler and Pearl
- Billboard rank: #65

Carl and Pearl Butler, a husband-and-wife pair, propelled this song to the top of the country charts in 1962. "Don't Let Me Cross Over" was the longest-running #1 duet until it was unseated in May 2013 by Florida Georgia Line's "Cruise."

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Kevin Winter // Getty Images

#64. 'Before He Cheats' by Carrie Underwood

- Artist: Carrie Underwood
- Billboard rank: #64

Though country star Carrie Underwood has her fair share of chart-topping hits, “Before He Cheats” entered the unofficial country music hall of fame in 2006. It spent 64 consecutive weeks on the Billboard Hot 100. 

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Mercury Records // Wikimedia Commons

#63. 'Country Girl' by Faron Young

- Artist: Faron Young
- Billboard rank: #63

Faron Young’s 1959 single stayed on the country charts for 32 weeks. The song follows a narrator heartbroken by a “country girl” who leaves him even though she seems happy. 

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Rick Diamond // Getty Images

#62. 'I'll Get Over You' by Crystal Gayle

- Artist: Crystal Gayle
- Billboard rank: #62

This 1976 recording was Crystal Gayle’s first #1 country hit, which proved to be a step in the right direction. At the time, Gayle was trying to achieve the same level of fame as her older sister, Loretta Lynn.

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Matthew D. Leistikow // Wikimedia Commons

#61. 'Achy Breaky Heart' by Billy Ray Cyrus

- Artist: Billy Ray Cyrus
- Billboard rank: #61

This song was originally recorded by another band under a different title, the year before Billy Ray Cyrus’ monumental 1992 song hit #4 on the Billboard Hot 100. Though the song originally received critical reviews, it has become a cult classic.

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Kevin Winter // Getty Images

#60. 'I Like It, I Love It' by Tim McGraw

- Artist: Tim McGraw
- Billboard rank: #60

In Tim McGraw’s fast-paced 1995 hit, he expresses how deeply in love he is with his romantic partner. In the years since its release, the song has been featured in dozens of promotional videos for various athletic events.

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Gage Skidmore // Wikimedia Commons

#59. 'Why Don't We Just Dance' by Josh Turner

- Artist: Josh Turner
- Billboard rank: #59

In his 2009 single, Josh Turner tells the story of a couple that dances together in their living room to forget all the troubles in the world.

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Gage Skidmore // Wikimedia Commons

#58. 'My Maria' by Brooks & Dunn

- Artist: Brooks & Dunn
- Billboard rank: #58

"My Maria," which was originally recorded in 1973, won Brooks & Dunn their second Grammy Award for Best Country Performance by a Vocal Group or Duo. Billboard also declared "My Maria" the #1 country song of the year.

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Rick Diamond // Getty Images

#57. 'Party Time' by T.G. Sheppard

- Artist: T. G. Sheppard
- Billboard rank: #57

This #1 hit was T.G. Sheppard’s eighth and remained on the country charts for 13 weeks. The upbeat recording follows a narrator as he attempts to party hard enough to forget about a breakup.
 

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H. Michael Karshis // Wikimedia Commons

#56. 'Every Which Way But Loose' by Eddie Rabbitt

- Artist: Eddie Rabbitt
- Billboard rank: #56

Not to be confused with a film by the same name, this 1979 song set a record for the highest debut on the Hot Country Singles chart. It took nearly 30 years for another song to top it. "Every Which Way But Loose" follows a narrator who has positive and negative feelings toward his girlfriend, who he can’t seem to break up with.

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Hubert Long // Wikimedia Commons

#55. 'Wings Of A Dove' by Ferlin Husky

- Artist: Ferlin Husky
- Billboard rank: #55

Though the song was originally recorded in 1958 by Bob Ferguson, it found true popularity when Ferlin Husky released his cover in 1960. The song alludes to a verse in the Bible in which God sends Noah a dove during the flood. "Wings Of A Dove"  has since been covered by more than a dozen country artists.

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United Talent Inc. // Wikimedia Commons

#54. 'You've Never Been This Far Before' by Conway Twitty

- Artist: Conway Twitty
- Billboard rank: #54

The controversial song describes a romantic rendezvous between a man and his much less-experienced girlfriend. Though there was a public outcry about the song’s raunchy lyrics in 1973, it became Conway Twitty’s only song to cross over from the country charts to the Top 40 of the Billboard Hot 100, where it peaked at #22.

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Rick Diamond // Getty Images

#53. 'As Good As I Once Was' by Toby Keith

- Artist: Toby Keith
- Billboard rank: #53

This ballad of an aging cowboy quickly became one of Toby Keith’s most successful songs of all time. It reached the top of the country charts in 2005.

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Scott Gries // Getty Images

#52. 'Love Without End, Amen' by George Strait

- Artist: George Strait
- Billboard rank: #52

George Strait’s 1990 single helped him break out of the "good country singers" mold to become a legend. "Love Without End, Amen" stayed at #1 on the country charts for several weeks. The emotional ballad follows a man through his life as he discovers unconditional love.

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Bradford Timeline // Flickr

#51. 'Hello Darlin'' by Conway Twitty

- Artist: Conway Twitty
- Billboard rank: #51

Conway Twitty’s 1970 song about a man’s emotional encounter with a former flame soon became one of his signature performances. The single was his fourth to top the country charts, and Billboard declared it the #1 song of the year.

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Jace Afsoon // Unsplash

#50. 'Easy Loving' by Freddie Hart

- Artist: Freddie Hart
- Billboard rank: #50

This 1971 summer jam became Freddie Hart’s breakthrough hit, as well as a country music classic. Heart lost his record contract when an earlier song didn't do as well as expected. A radio station picked up this tune about a loving, committed relationship, and brought Hart back into stardom.

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Vistadeck // Wikimedia Commons

#49. 'When You Say Nothing At All' by Keith Whitley

- Artist: Keith Whitley
- Billboard rank: #49

“When You Say Nothing At All” is one of the most important songs in the careers of three different artistsbut only Keith Whitley’s version reached the top of the country charts in the United States. The 1988 single is a touching love letter to a romantic partner whose silence speaks volumes. 

 

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Frazer Harrison // Getty Images

#48. 'Houston (Means I'm One Day Closer To You)' by Larry Gatlin & The Gatlin Brothers

- Artist: Larry Gatlin & The Gatlin Brothers
- Billboard rank: #48

The 1983 recording was the Gatlin Brothers’ third and final #1 hit on the country chart. In the emotional song, the narrator tells his romantic partner he's looking forward to finishing his concert tour, so he can return home.

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University of Houston // Wikimedia Commons

#47. 'Coward Of The County' by Kenny Rogers

- Artist: Kenny Rogers
- Billboard rank: #47

This playful ballad follows a “cowardly” young man who learns to stand up for himself despite his father’s advice to the contrary. The 1980 recording hit #1 on the country charts, and even crossed over to hit #3 on the pop charts. 

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Monument Record Corp. // Wikimedia Commons

#46. 'Skip A Rope' by Henson Cargill

- Artist: Henson Cargill
- Billboard rank: #46

This 1967 single encouraged parents to listen to their children when they talk about social issues, like racism and bullying. "Skip A Rope" topped the country charts, and crossed over to the Billboard Hot 100, where it peaked at #25.

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pasphotography // Shutterstock

#45. 'The Good Stuff' by Kenny Chesney

- Artist: Kenny Chesney
- Billboard rank: #45

Though Kenny Chesney is most famous for recording several hit songs about drinking and the beach, his ballad about a man finding that "the good stuff" in life is love for a woman was his longest lasting #1 single on the country charts.

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David L. Smart // Wikimedia Commons

#44. 'That's What I Love About Sunday' by Craig Morgan

- Artist: Craig Morgan
- Billboard rank: #44

In 2005, “What I Love About Sunday” became Craig Morgan’s only #1 country single. The song, which was declared the #1 hit of the year by Billboard, is a man’s heartfelt ode to family time and an easygoing lifestyle.

 

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Ethan Miller // Getty Images

#43. 'Burnin' It Down' by Jason Aldean

- Artist: Jason Aldean
- Billboard rank: #43

This sultry ballad sparked controversy on the radio for its suggestive nature and electronic dance music-like sound, but "Burnin' It Down" still won Jason Aldean the Top Country Song category at the 2015 Billboard Music Awards.

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David Magbee

#42. 'Almost Persuaded' by David Houston

- Artist: David Houston
- Billboard rank: #42

David Houston’s cheeky 1966 recording is about a man who's about to be unfaithful to his wife when he sees the reflection of his wedding band and flees the dance floor. The single spent nine weeks on the Billboard country charts.

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Spc. Lorie Jewell // Wikimedia Commons

#41. 'I Swear' by John Michael Montgomery

- Artist: John Michael Montgomery
- Billboard rank: #41

This 1994 ballad is a declaration of love in the form of a promise to be there no matter what. This version topped the country charts, and a cover by pop group All-4-One topped the Billboard Hot 100 the following year.

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Bill Steber // Getty Images

#40. 'Ain't Nothing 'Bout You' by Brooks & Dunn

- Artist: Brooks & Dunn
- Billboard rank: #40

This romantic single, a sharp departure from the duo’s usual honky-tonk style, spent six weeks at the top of the country charts. "Ain't Nothing 'Bout You" even crossed over to the top 40 of the Billboard Hot 100 in 2001.

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Neal Agency // Wikimedia Commons

#39. 'You're The Only World I Know' by Sonny James

- Artist: Sonny James
- Billboard rank: #39

The 1965 declaration of love was Sonny James’ second #1 single, and launched a decade of popularity. From 1965 to 1974, 22 of James’ songs reached #1—including a string of 16 straight hits.

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Jack Kay // Getty Images

#38. 'Rose Garden' by Lynn Anderson

- Artist: Lynn Anderson
- Billboard rank: #38

Lynn Anderson’s 1970 recording of Billy Joe Royal’s 1967 song has an unlikely success story. Anderson had to fight to record it, because critics thought of it as a “man’s song.” Her single reached the top of the country charts, then crossed over to the pop charts, where it peaked at #3.

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Kevin Winter // Getty Images

#37. 'Watching You' by Rodney Atkins

- Artist: Rodney Atkins
- Billboard rank: #37

This heartwarming, upbeat song about a father's close relationship with his child was named the #1 song of 2007 on Billboard's year-end chart. 

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Rick Diamond // Getty Images

#36. 'Mammas Don't Let Your Babies Grow Up To Be Cowboys' by Sara Evans and Deana Carter

- Artist: Sara Evans and Deana Carter
- Billboard rank: #36

Though the song was originally recorded in 1973 and has been covered by several country stars to-date, it’s the 2003 Sara Evans and Deana Carter version that climbed the charts. The song serves as a warning to the loved ones of cowboys, while also paying tribute to the hardships of the job. 

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Paras Griffin // Getty Images

#35. 'Don't Blink' by Kenny Chesney

- Artist: Kenny Chesney
- Billboard rank: #35

“Don’t Blink” is Kenny Chesney’s 13th #1 country hit. The song tells the tale of an encounter with an elderly man, who is sharing the secret to a fulfilling life.

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thejointstaff // Flickr

#34. 'This Is How We Roll' by Florida Georgia Line (featuring Luke Bryan)

- Artist: Florida Georgia Line (featuring Luke Bryan)
- Billboard rank: #34

This 2012 party anthem combines the vocal talents of up-and-coming country legends Florida Georgia Line and Luke Bryan, who went on to win the CMA's coveted "Entertainer of the Year" award in 2014 and 2015. "This Is How We Roll" reached #1 on the country charts, and even cracked the Billboard Hot 100's top 15 songs.

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Scott Gries // Getty Images

#33. 'It's Five O'Clock Somewhere' by Alan Jackson and Jimmy Buffett

- Artist: Alan Jackson and Jimmy Buffett
- Billboard rank: #33

This 2003 duet between two musical legends won the CMA's "Vocal Event of the Year," and was named the #3 song of the decade on Billboard's country chart. The song is about friends at work who leave early to start drinking, because "it's 5 o'clock somewhere."

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Patrick Reviere // Getty Images

#32. 'Islands In The Stream' by Kenny Rogers with Dolly Parton

- Artist: Kenny Rogers duet with Dolly Parton
- Billboard rank: #32

This popular 1983 duet topped the Billboard Hot 100, and was one of the best-selling singles of the year. A pop crossover, the song follows the course of a couple’s fiery relationship, and was written and produced by the Bee Gees. 

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Michael Johnson // RCA

#31. 'Give Me Wings' by Michael Johnson

- Artist: Michael Johnson
- Billboard rank: #31

“Give Me Wings” was Michael Johnson’s third country hit, and his first of two hit country singles. The song is about a man whose love needs more space, to his dismay. 

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Gunner Eberlein // Wikimedia Commons

#30. 'All The Time' by Jack Greene

- Artist: Jack Greene
- Billboard rank: #30

Jack Greene covered Kitty Wells' 1959 song in 1967, shooting to #1 on the country charts. The simple song tells a familiar tale of undying love. 

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Bede735c // Wikimedia Commons

#29. 'I've Come To Expect It From You' by George Strait

- Artist: George Strait
- Billboard rank: #29

George Strait’s single hit #1 in 1990, and remained in the top spot for five weeks. The song's narrator expresses unhappiness with a lover who's left him. 

 

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GDuwen // Wikimedia Commons

#28. 'Heartaches By The Number' by Ray Price

- Artist: Ray Price
- Billboard rank: #28

This 1959 song was so popular that even its sheet music was a best-seller. More than a dozen artists have released covers of "Heartaches By The Number" over the years, several of which appeared on the country charts. The song lists all the times a lover has broken the narrator's heart.

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Ethan Miller // Getty Images

#27. 'Don't Let Our Love Start Slippin' Away' by Vince Gill

- Artist: Vince Gill
- Billboard rank: #27

Vince Gill, who boasts the record for most consecutive years hosting the CMAs (a whopping 12 times) released this single in 1992 at the start of his reign over country music. The song peaked at #1 on the country charts.

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Sterling Munksgard // Shutterstock

#26. 'Have Mercy' by The Judds

- Artist: The Judds
- Billboard rank: #26

The Judds' third song on the list of best country songs is yet another condemnation of a man who treats a woman poorly. The 1985 single spent 14 weeks on the country charts.

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Senior Airman Benjamin Stratton // U.S. Air Force

#25. 'Chattahoochee' by Alan Jackson

- Artist: Alan Jackson
- Billboard rank: #25

This fast-paced, heartfelt song filled country music fans with hopeful nostalgia. The 1993 song received CMA awards for Single of the Year and Song of the Year.

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Rusty Russell // Getty Images

#24. 'If You're Going Through Hell (Before The Devil Even Knows)' by Rodney Atkins

- Artist: Rodney Atkins
- Billboard rank: #24

Rodney Atkins’ upbeat anthem spent four weeks at the top of the country charts in 2005 before breaking into the Billboard Hot 100. The lyrics encourage listeners to keep on fighting when the going gets tough. 

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SUZANNE CORDEIRO/AFP via Getty Images

#23. 'Here You Come Again' by Dolly Parton

- Artist: Dolly Parton
- Billboard rank: #23

Dolly Parton’s first big pop crossover hit topped the country charts for five weeks and earned her a Grammy for Best Female Country Vocal Performance. Parton’s song, in which she sings about a man she just can’t seem to get over, has been covered more than a dozen times.

 

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#22. 'How Do You Like Me Now?!' by Toby Keith

- Artist: Toby Keith
- Billboard rank: #22

Toby Keith sings to a girl who once rejected him, flaunting his newfound fame in this 1999 honky-tonk jam. The song earned several award nominations, and hit the top of the country chart, breaking into the Top 40 as well.

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Capitol Records // Wikimedia Commons

#21. 'Rhinestone Cowboy' by Glen Campbell

- Artist: Glen Campbell
- Billboard rank: #21

Country music legend Glen Campbell’s hit “Rhinestone Cowboy” resonated with any country music fan who ever dreamed of becoming a star. The 1975 hit has been covered by artists like Blake Shelton and Tim McGraw. 

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Bede735 // Wikimedia Commons

#20. 'Check Yes Or No' by George Strait

- Artist: George Strait
- Billboard rank: #20

This playful song is an ode to a lover, whose relationship with the narrator started when they were just kids. The single hit #1 on the country charts in United States and Canada.

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Kathy Hutchins // Shutterstock

#19. 'It's Your Love' by Tim McGraw with Faith Hill

- Artist: Tim McGraw with Faith Hill
- Billboard rank: #19

This collaboration between one of the most famous couples in country music is not their only duet, but it was the most successful. The 1997 song spent six weeks at the top of the country charts and became both musicians' first top 10 hit on the Billboard Hot 100.

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Emma Frances Logan // Unsplash

#18. 'My Hang-Up Is You' by Freddie Hart

- Artist: Freddie Hart
- Billboard rank: #18

“My Hang-Up Is You” was Freddie Hart’s second #1 hit on the country charts, remaining at the top for six consecutive weeks. The song's narrator admits that his greatest weakness in life is the person he loves.

 

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Staff Sgt. Patrick Moes // Wikimedia Commons

#17. '19 Somethin'' by Mark Wills

- Artist: Mark Wills
- Billboard rank: #17

Mark Willis’ musical ode to each decade of the late 20th century spent six weeks at #1 on the country charts and peaked at #23 on the Hot 100.

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majunznk // Flickr

#16. 'Luckenbach, Texas (Back To The Basics Of Love)' by Waylon Jennings

- Artist: Waylon Jennings
- Billboard rank: #16

This 1977 song about a couple who returns to country living after high society takes its toll on their relationship, made waves on both pop and country charts.

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Gabe Palacio // Getty Images

#15. 'Live Like You Were Dying' by Tim McGraw

- Artist: Tim McGraw
- Billboard rank: #15

Tim McGraw’s 2004 hit is an ode to loved ones struggling with cancer. It won several major awards, including Single of the Year and Song of the Year at the CMAs, and Best Country Song at the Grammys.

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Ethan Miller // Getty Images

#14. 'Need You Now' by Lady Antebellum

- Artist: Lady Antebellum
- Billboard rank: #14

The 2009 song, about an on-again, off-again relationship, won four Grammy Awards in 2011, including Song of the Year and Record of the Year. In 2011, "Need You Now" became the most downloaded country song, surpassing Taylor Swift’s "Love Story."

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#13. 'Once A Day' by Connie Smith

- Artist: Connie Smith
- Billboard rank: #13

“Once A Day” spent eight weeks at the top of the country charts in 1964, setting the record for the most weeks spent at #1 by a female country artist. It was surpassed by Taylor Swift’s “We Are Never Getting Back Together.”

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#12. 'Just To See You Smile' by Tim McGraw

- Artist: Tim McGraw
- Billboard rank: #12

McGraw's 1997 single spent 42 weeks on the Billboard country chart, setting the record for the longest run of all time. The song's narrator pledges he will do anything to make his loved one smile.

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#11. 'Kiss An Angel Good Mornin'' by Charley Pride

- Artist: Charley Pride
- Billboard rank: #11

This song was Pride’s eighth to top the country charts, and it spent four months on the pop chart. It follows a man's unconditional love for the woman he wakes up to. 

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Heinrich Klaffs // Wikimedia Commons

#10. 'Daddy Sang Bass' by Johnny Cash

- Artist: Johnny Cash
- Billboard rank: #10

This 1986 hit is the most successful of dozens of Johnny Cash’s melancholy songs. The narrator’s family attempts to stay close, despite the passing of his brother. It stayed #1 on the country charts for six weeks.

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Frederick M. Brown // Getty Images

#9. 'Amazed' by Lonestar

- Artist: Lonestar
- Billboard rank: #9

The country group Lone Star’s 1999 hit spent eight weeks at the top of the Billboard country chart. A remix of the song hit #1 on the Billboard Hot 100. The single is a powerful declaration of a man’s love for his romantic partner, whose every move leaves him “amazed.”

 

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Craig ONeal // Wikimedia Commons

#8. 'Somebody Like You' by Keith Urban

- Artist: Keith Urban
- Billboard rank: #8

Keith Urban’s 2002 single, which Billboard dubbed the #1 country song of the first decade of the 21st century, is a simple love song. The narrator has finally found a woman who makes him forget about life's troubles.

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Dalibor Bosnjakovic // Unsplash

#7. 'Convoy' by C. W. McCall

- Artist: C. W. McCall
- Billboard rank: #7

C. W. McCall’s 1975 song hit #1 on both country and pop charts. The song, laced with trucker slang, follows a group of truck drivers through a protest.

 

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Warner Brothers Records // Wikimedia Commons

#6. 'Love's Gonna Live Here' by Buck Owens

- Artist: Buck Owens
- Billboard rank: #6

Buck Owens’ 1963 hit held the top spot for 16 weeks, a record that stood for a jaw-dropping 49 years. The song follows the narrator’s recovery from a breakup, and excitement about falling in love in the future.

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#5. 'There Goes My Everything' by Jack Greene

- Artist: Jack Greene
- Billboard rank: #5

Jack Greene’s song about a tough breakup peaked at #65 on the Billboard Hot 100 in 1966 and spent seven weeks at the top of the country chart.

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Mario957 // Wikimedia Commons

#4. 'Take Your Time' by Sam Hunt

- Artist: Sam Hunt
- Billboard rank: #4

This 2014 recording became Hunt's second consecutive single to reach #1 on the country charts. The narrator seeks a romantic encounter with someone he meets in a crowd.

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CraigShipp.com // Wikimedia Commons

#3. 'Wanted' by Hunter Hayes

- Artist: Hunter Hayes
- Billboard rank: #3

Hunter Hayes broke a record held since 1973 as the youngest male artist to reach #1 when “Wanted” topped the Hot Country Songs chart. His second single, a love song, helped him win the CMA award for Best New Artist in 2012.

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Courtesy Leroy Van Dyke

#2. 'Walk On By' by Leroy Van Dyke

- Artist: Leroy Van Dyke
- Billboard rank: #2

Leroy Van Dyke’s most successful song spent 37 weeks on the country chart in 1961, with a record-breaking 19 in the #1 spot. It was one of the first country-rock songs that inspired bands like The Eagles.

 

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Rick Diamon // Getty Images

#1. 'Cruise' by Florida Georgia Line

- Artist: Florida Georgia Line
- Billboard rank: #1

The duo’s 2012 single set an all-time record of 56 weeks on the country charts, tying Taylor Swift’s record. The remix, which featured rapper Nelly, hit #6 on the Hot 100. In 2013, “Cruise” became the best-selling song by a country duo in digital history.

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