| 100% | RED | 3 | 41-Across album that won two Billboard Music Awards in 2013 |
| 88% | RED | 3 | Taylor Swift album that won two Billboard Music Awards in 2013 |
| 53% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 44% | ADELE | 5 | She won 12 Billboard Music Awards in 2012 |
| 40% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 40% | ANTI | 4 | Rihanna album that won Favorite Soul/R&B Album at the 2016 American Music Awards |
| 40% | HILDA | 5 | Animated drama series that won two Daytime Emmy awards in 2021 |
| 39% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 39% | JEAN | 4 | "Billie ___," the second single from Michael Jackson's album in 16a, that won two Grammys and one American Music Award |
| 38% | ZAYN | 4 | "Pillowtalk" singer who won the Billboard Music Award for New Artist of the Year as a member of One Direction in 2013 and as a solo artist in 2017 |
| 38% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 38% | AHA | 3 | Band that won six MTV Video Music Awards for "Take On Me" in 1986 (Hyph.) |
| 37% | CELTICTHUNDER | 13 | Irish vocal group that won Billboard's Top World Album Artist award three times: 2 wds. |
| 36% | WASTED | 6 | Carrie Underwood song that won Most Performed Song of the Year in the 2007 ASCAP Country Music Awards |
| 36% | IRREPLACEABLE | 13 | Beyoncé hit song that won the Soul Train Music Award for Best R&B/Soul Single in 2007 |
| 36% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 36% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 35% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 35% | DAWN | 4 | "___ FM," 2022 music album by the Weeknd that debuted at number two on the US Billboard 200 |
| 35% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 35% | 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.) |
| 35% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 34% | ARIANAGRANDE | 12 | 2013 American Music Awards New Artist of the Year whose sixth studio album, "Positions," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 34% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 34% | 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 |
| 34% | DAMN | 4 | Kendrick Lamar album that won the Pulitzer Prize for Music |
| 34% | GABBYBARRETT | 12 | "I Hope" singer who won three Billboard Music Awards, including Top Country Female Artist, in 2021 (2 wds.) |
| 34% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 34% | DAMN | 4 | 2017 Kendrick Lamar album that won the Pulitzer Prize for Music |
| 34% | SOUL | 4 | Animated film starring Jamie Foxx that won two Oscars in 2021 |