Billboard magazine has been around for more than a hundred years, and the magazine has tracked the most popular songs in music since 1936. The Billboard charts tell the story of a year in music—not the best songs or the most important ones, but the ones that played again and again on the radio waves. Pop music is a shared history for people of a certain age; almost everyone knows the words to their era's #1 hits, whether that be “Bridge Over Troubled Water” or “In Da Club.”
In 1990, Billboard began hosting the Billboard Music Awards. This year's awards ceremony, hosted by Kelly Clarkson, will be held at the MGM Grand in Las Vegas on May 1. While the Grammys mirror the Oscars with Academy voters selecting the winners, the Billboard Music Awards are much more algorithmic. The awarded artists are decided based on popularity, sales, radio play, tour revenue, and other factors. This award ceremony took a four-year hiatus from 2007 to 2010 before returning with slightly different categories in 2011. It's likely some of the most decorated artists in Billboard Music Award history would have received more awards to their name, if not for the break.
Though music genres have become increasingly fluid, it's reasonable to classify four of the top 16 Billboard Music Award winners as rappers and 2.5 as country singers. However, the majority of winners are R&B singers. While the Grammy voters have held onto rock 'n' roll, the numbers don't lie: there's not a single rock band among the top 16 most decorated artists. Many believe this is an era of hip hop, R&B, dance music, and country—even more straightforward “pop” music is some amorphous mix of two or more of those genres.
Stacker scoured Billboard's Top Winners Leaderboard to present readers with this list of 16 artists who have garnered the most Billboard Music Awards since the award show's conception in 1990. They are ranked by the number of awards won. All artists who have won Billboard awards in any category were considered.
Read on to discover the two most celebrated artists, who were able to move impressively between genres. One started in teen pop and moved onto R&B, and the other started as a country artist and became a pop star.
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Awards won: 10
R&B legend Mary J. Blige has been winning music and acting awards for an incredible three decades. Her 1994 album “My Life” was awarded Billboard's R&B Album of the Year in 1995. The album was also ranked #281 on Rolling Stone's list of 500 greatest albums of all time. In 2005, Blige released “The Breakthrough” which cleaned up at the Billboard Music Awards. She won nine awards at the 2006 event, including R&B/Hip-Hop Song of the Year for her megahit “Be Without You,” which spent 33 weeks on the Billboard charts.
Awards won: 10
It's hard to remember, given his precipitous fall, but there was a time around the year 2000 when Eminem was considered the best rapper alive. The antagonistic singer from Detroit broke through with guest spots on Dr. Dre's “2001” before putting out back-to-back classic albums. Eminem won his first Billboard Music Award for “The Eminem Show," which nabbed 2002's Album of the Year. In 2009, the rapper was named Billboard's Artist of the Decade for the 2000s.
Awards won: 10
Before she was a one-name industry-dominating force of nature, Beyoncé Knowles was the frontwoman for Destiny's Child, a girl group out of Houston, Texas, that became a powerhouse in its own right. Beyoncé sang beside Kelly Rowland and Michelle Williams, and the band broke through with its second album, “The Writing's On The Wall,” before hitting its ultimate peak with the 2001 release of the album “Survivor.” Destiny's Child had four #1 hits, a #2 hit, and four #3 hits during its 16-year run. The band won Artist of the Year in 2000 and 2001, and Beyoncé won Top Female Artist of the Decade for the 2000s.
Awards won: 10
After winning season four of “American Idol,” country singer Carrie Underwood became a force on the country and Top 40 charts, selling more than 65 million records in her 14-year career. Underwood's 2005 debut album “Some Hearts” earned her the Grammy for Best New Artist, and her next three albums all debuted at #1 on the all-genre Billboard 200. She is the first female singer to have four country albums land atop the Billboard 200 charts. Underwood has won 10 Billboard Music Awards and is nominated for two more for her 2018 album “Cry Pretty.” She is considered to be the most successful "American Idol" winner in the show's history.
Awards won: 10
The Queens-born rapper first made a name for himself with the track “How to Rob,” in which he detailed ways he'd stick up well-known and prominent artists. The young rapper seemed on his way, but was shot and nearly killed while sitting in a car in Jamaica, Queens. 50 Cent recovered and was signed by Dr. Dre and Eminem. His debut album “Get Rich or Die Tryin'” came out in February 2003 and vaulted 50 Cent to rap's elite. The legendary album sold 6 million copies that year, and earned 50 Cent five Grammy nominations and two #1 hits. 50 Cent won 10 Billboard Music Awards between 2003 and 2005. He hasn't won one since.
Awards won: 11
The Atlanta DJ was instrumental in mainstreaming crunk, a fast-paced rap genre out of Atlanta. Along with his band The East Side Boyz, Lil Jon hit the scene with their debut album “Get Crunk, Who U Wit: Da Album” in 1997. Lil Jon & the East Side Boyz only grew more prominent with each of their next four releases, which included charting singles “Bia' Bia',” “Lovers and Friends,” and “Get Low.” When Lil Jon went solo in 2006, he didn't slow down, charting again with “Snap Yo Fingers” and much later with 2013's “Turn Down for What.” (The latter's music video has been viewed nearly 850 million times on YouTube.) Lil Jon was also regularly featured on songs by other prominent Atlanta acts, including Usher, Ludacris, Ying Yang Twins, and YoungBloodZ. Lil Jon won the first three of his 11 Billboard Music Awards in 2003—including R&B/Hip Hop Group of the Year—and his last in 2015 for “Turn Down for What.”
Awards won: 11
The youngest of the Jackson children, Janet Jackson began performing on stage at giant venues and acting in TV shows at age 7. Jackson put out her first two solo albums as a teenager. However, it was her third album, “Control,” released in 1986, that announced Jackson as a force-of-nature pop star. “When I Think of You” became Jackson's first #1 hit. She had nine more chart-topping singles during her career. Jackson won her first eight Billboard Music Awards at the 1990 event, following her mega-selling 1989 album “Janet Jackson's Rhythm Nation 1814” which is the only album to have a #1 single chart in three separate calendar years. She won the ICON Award, her 11th Billboard Music Award, in 2018.
Awards won: 12
It's hard to remember a world before Rihanna, but the singer from Barbados only broke into the music industry in 2005. Rihanna first hit #1 on the charts with “SOS” in May 2006 and followed it up with the megahit “Umbrella” in June 2007. Rihanna has had an incredible 14 #1 hits and has had 31 songs hit the Billboard Top 10. She has won 12 Billboard Music Awards and has been nominated 68 times. Rihanna also started two gigantic fashion brands—Fenty Beauty and Savage Lingerie—and has an estimated worth of $210 million.
(Editor's note: R. Kelly tied with Rihanna for 12 awards, but has not been included in the gallery due to recent controversies surrounding the artist.)
Awards won: 14
Mariah Carey has a voice to be reckoned with. She can hit five octaves and sing higher than anyone in Rolling Stone's list of 100 greatest singers of all time. Following her iconic performance at the 33rd Grammy Awards (held in late February 1991), her self-titled debut rocketed to the top of the charts, where it stayed for 11 straight weeks. In total, Carey has an amazing 18 #1 hits spread over 18 years. Carey's 1994 Christmas song “All I Want for Christmas Is You” is the most downloaded holiday song in history. She won 14 Billboard Music Awards between 1991 and 2005 and will win her 15th this year when she receives the ICON Award.
Awards won: 15
Drake first started stealing hearts and minds with his performance as Jimmy Brooks on the Canadian teen drama “Degrassi: The Next Generation.” In 2009, the rapper self-released his third mixtape “So Far Gone,” which became a viral success. One of the album's singles, “Best I Ever Had,” hit #2 on the charts. The next year, Drake released his first major-label album, “Thank Me Later,” which debuted at #1. Drake is one of the most popular artists of the 2010s, mainly due to his ability to dominate the streaming platforms. In 2018, his streams accounted for 1.2% of all music streams worldwide; his songs were streamed 6.4 billion times in 2017 and 11.13 billion times in 2018. Drake has won 15 Billboard Music Awards total, collecting 13 of them in a single record-breaking night at the 2017 awards show, following the release of his 2016 album “Views.”
Awards won: 16
One of the true powerhouse divas in history, Whitney Houston arrived at age 19 ready to take over the music world. Her first two studio albums hit #1 on the Billboard 200, and she had 11 #1 hits between 1985 and 1995. In 1992, Houston starred alongside Kevin Costner in “The Bodyguard,” and her soundtrack for the film is the best-selling in history. Her cover of Dolly Parton's “I Will Always Love You” is the best-selling single by a female artist in history. Houston won 11 of her 16 Billboard Music Awards in 1993 following the record-breaking release of “The Bodyguard” soundtrack. She won her final award at the 2012 event posthumously, after she died of an overdose earlier that year.
Awards won: 18
With a truly striking voice, the British singer Adele broke onto the international scene with her 2008 debut album “19.” Adele won Best New Artist at the 2008 Grammys, but it was her second album “21” that rocketed her to the music industry's throne. “21” hit #1 on the Billboard 200 and stayed there for 24 weeks; it was on the charts for a ridiculous 411 weeks. In 2015, Adele released her third album, “25,” which also hit #1 on the Billboard 200. “21” had three #1 hits, including “Rolling in the Deep,” and her “25” album had one, “Hello.” Adele won a then-record 12 Billboard Music Awards in 2012 following “21.” She won five more in 2016, amounting to 18 total wins.
Awards won: 18
Usher released his first album in 1994, but it wasn't until a decade later that it became clear the R&B singer was a legendary performer. His 2004 album “Confessions” dominated the year, eventually hitting 10 million sales in 2012. Four of Usher's nine #1 hits were on his classic album, including “Yeah!” which spent 12 weeks in the top spot. Usher won 11 awards at the Billboard Music Awards in 2004, including Billboard 200 Album of the Year. He has 18 in total. Usher won R&B/Hip-Hop Artist of the Year in 1998 and was nominated again 15 years later in 2013.
Awards won: 19
Garth Brooks became a country star the instant he released his self-titled debut album in 1989, but it was his 1990 second album “No Fences” that made him a crossover star. The album featured his classic song “Friends in Low Places” and vaulted to #3 on the Billboard 200. Brooks followed “No Fences” with megahit after megahit. As of last year, he sold the second most records in history (148 million), trailing only The Beatles. Brooks has been nominated for 23 Billboard Music Awards and has won 19; he'll be awarded Artist of the Decade at this year's awards.
Awards won: 20
Justin Bieber was famously discovered at 14 by manager Scooter Braun, who saw the young Canadian's YouTube videos and signed him, along with Usher and L.A. Reid. The next year, in 2009, Bieber put out his debut EP “My World,” which hit #5 on the Billboard 200. The teenager was a singing and dancing phenom and quickly followed up his debut with three full-length albums from 2010 to 2012 which all hit #1. Bieber's 2015 album “Purpose” featured “Sorry,” “What Do You Mean?” and “Love Yourself,” which each topped the Billboard Hot 100. In 2017, he hopped on tracks by DJ Khaled, Daddy Yankee, and Luis Fonsi, which hit #1. But early stardom has led to some instability for Bieber, who has found himself in trouble and then deeply into religion. He took two years off performing before surprising fans with a cameo at Ariana Grande's 2019 Coachella performance. Bieber has won 20 awards and has been nominated 48 times. His first seven wins came in 2011, and he won five more awards at the 2018 ceremony.
Awards won: 23
Love her or hate her—it's impossible to deny the genius of Taylor Swift. The Nashville pop star released her self-titled debut country album at 16 and instantly became a force on the Billboard charts. That album peaked at #5 and featured “Our Song,” which hit #1. Her 2008 follow-up, “Fearless,” was the best-selling album of 2009 and won the Grammy for Album of the Year. (She won a second Album of the Year Grammy in 2015 for “1989.”) In 2012, Swift shifted from country to pop with her album “Red.” She nabbed her first #1 hit with “We Are Never Ever Getting Back Together” in September of that year. Swift has become one of the wealthiest musicians in history, with an estimated worth of $320 million. Her 2018 Reputation Stadium Tour was the most lucrative in music history, bringing in $266.1 million. Swift has won a record 23 Billboard Music Awards, netting eight in both 2013 and 2015. She's nominated for Top Female Artist and Top Touring Artist at this year's ceremony.