| 100% | OLDTOWNROAD | 11 | Lil Nas X and Billy Ray Cyrus song that won the 2019 American Music Award for Favorite Rap/Hip-Hop Song (3 wds.) |
| 56% | OLDTOWNROAD | 11 | Song for which Lil Nas X and Billy Ray Cyrus won the Grammy for Best Pop Duo/Group Performance in 2020: 3 wds. |
| 49% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 46% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 41% | SICKOMODE | 9 | Travis Scott song that won the 2019 Billboard Music Award for Top Streaming Song (Audio) (2 wds.) |
| 40% | SEBASTIANYATRA | 14 | "Dos Oruguitas" singer who won the 2022 American Music Award for Favorite Latin Song (2 wds.) |
| 40% | OLDTOWNROAD | 11 | 2019 Lil Nas X song that topped the charts for 19 weeks, the longest of the 2010s: 3 wds. |
| 40% | INDUSTRYBABY | 12 | 2021 Lil Nas X and Jack Harlow song that was #1 on the Hot R&B/Hip-Hop charts for 18 weeks: 2 wds. |
| 39% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |
| 39% | CARDIB | 6 | "Up" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist twice: 2 wds. |
| 39% | NICKIMINAJ | 10 | "Anaconda" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times: 2 wds. |
| 39% | IGGYAZALEA | 10 | "Fancy" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist in 2014: 2 wds. |
| 35% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper whose "Rockstar" won the 2018 Billboard Music Award for Top Rap Song and the 2018 MTV Video Music Award for Song of the Year (2 wds.) |
| 35% | BILLIEEILISH | 12 | "All the Good Girls Go to Hell" singer who won the 2019 American Music Award for New Artist of the Year (2 wds.) |
| 35% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 35% | ABOUTDAMNTIME | 13 | Lizzo song that won the People's Choice Award for Song of 2022: 3 wds. |
| 35% | OLDTOWNROAD | 11 | 2019 song by Lil Nas X which peaked at number one on the Billboard Hot 100 for nineteen consecutive weeks: 3 wds. |
| 35% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 35% | EMINEM | 6 | "Lucky You" rapper who won the American Music Award for Favorite Rap/Hip-Hop Artist four times |
| 35% | GREENBOOK | 9 | American comedy-drama film that won the 2019 Golden Globe Award for Best Motion Picture - Musical or Comedy: 2 wds. |
| 34% | LITTLEBIGTOWN | 13 | Music group nominated for the 2017 American Music Award for Favorite Duo or Group—Country (3 wds.) |
| 34% | KNOWNOBETTER | 12 | Major Lazer song featuring Travis Scott, Camila Cabello, and Quavo that won the 2017 Teen Choice Award for Choice Electronic/Dance Song (3 wds.) |
| 34% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |
| 34% | OLDTOWNROAD | 11 | 2019 song by 44-Across whose remix version with Billy Ray Cyrus won two Grammy Awards (3 wds.) |
| 34% | LITTLEBIGTOWN | 13 | 15-Across and 54-Across band that won the 2017 Country Music Association Award for Vocal Group of the Year (3 wds.) |
| 34% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 33% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 33% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 33% | THELONDON | 9 | Young Thug song featuring J. Cole and Travis Scott that was nominated for the 2019 MTV Video Music Award for Song of Summer (2 wds.) |
| 33% | STRANGERTHINGS | 14 | Netflix horror series that won the People's Choice Awards for the Show of 2019 and the Drama Show of 2019 (2 wds.) |