| 100% | GARTHBROOKS | 11 | "Friends in Low Places" singer who has won the third-most Billboard Music Awards (19) (2 wds.) |
| 65% | JUSTINBIEBER | 12 | "Love Yourself" singer who has won the second-most Billboard Music Awards (21) (2 wds.) |
| 60% | TAYLORSWIFT | 11 | "Look What You Made Me Do" singer who has won the most Billboard Music Awards (23) (2 wds.) |
| 59% | GARTHBROOKS | 11 | "Friends in Low Places" singer who won the 2020 Gershwin Prize: 2 wds. |
| 55% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 52% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 52% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 51% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 51% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 51% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 51% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 51% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 51% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 51% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 50% | CYNDILAUPER | 11 | "Girls Just Want to Have Fun" singer who received the Billboard Women in Music Icon Award in 2018: 2 wds. |
| 50% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 50% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who has won two "Billboard" Music Awards and a "Billboard" Women in Music Chart-Topper Award (2 wds.) |
| 50% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 50% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 48% | SALVADORPEREZ | 13 | Kansas City Royal who has won 4 Silver Slugger awards, the most of any active catcher in the MLB (2 wds.) |
| 48% | LITTLEBIGTOWN | 13 | "Better Man" singers who have won the Country Music Association Award for Vocal Group of the Year six times (3 wds.) |
| 47% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 47% | DETROITRED | 10 | "___ Wings," American profession ice hockey team who have won the most Stanley Cup championships of NHL franchise in USA: 2 wds. |
| 46% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 46% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 46% | TAYLORSWIFT | 11 | "Love Story" singer-songwriter who won the award for Top Female Artist in Billboard 2018: 2 wds. |
| 46% | JENNIFERLOPEZ | 13 | "Waiting for Tonight" singer who received the Billboard Icon Award in 2014: 2 wds. |
| 46% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 46% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 45% | JOHNWILLIAMS | 12 | Film music composer who has won 24 Grammy Awards, five Oscars, and four Golden Globes in the last six decades (2 wds.) |