| 100% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 44% | STUCKWITH | 9 | "___ U," song by Ariana Grande and Justin Bieber (birthday today) which won an MTV Video Music Award in 2020: 2 wds. |
| 43% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 42% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 41% | 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 |
| 40% | DRAMA | 5 | "No More ___," 2001 Mary J. Blige song which won an MTV Video Music Award for Best R&B Video |
| 40% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 40% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 40% | SLEDGEHAMMER | 12 | Song that accounted for 9 of the 10 MTV Video Music Awards won by 17-Across in 1987 |
| 40% | AHA | 3 | Band that won six MTV Video Music Awards for "Take On Me" in 1986 (Hyph.) |
| 40% | 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.) |
| 39% | CAMILACABELLO | 13 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 18-Across (2 wds.) |
| 39% | SHAWNMENDES | 11 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 32-Across (2 wds.) |
| 38% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 38% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 38% | IRREPLACEABLE | 13 | Beyoncé hit song that won the Soul Train Music Award for Best R&B/Soul Single in 2007 |
| 38% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 37% | MYHEAD | 6 | "Can't Get You Out of ___," hit song by Australian singer Kylie Minogue which won an MTV Video Music Award in 2002: 2 wds. |
| 37% | BLANKSPACE | 10 | Taylor Swift song that won the 2015 MTV VMA for Best Female Video: 2 wds. |
| 37% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 37% | UPTOWNFUNK | 10 | Mark Ronson/Bruno Mars song that won the 2015 MTV VMA for Best Male Video: 2 wds. |
| 37% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 36% | WASTED | 6 | Carrie Underwood song that won Most Performed Song of the Year in the 2007 ASCAP Country Music Awards |
| 36% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 36% | AHA | 3 | Band that won five MTV Video Music Awards for "Take On Me" (Hyph.) |
| 36% | AHA | 3 | Band that won six MTV Video Music Awards for "Take On Me" (Hyph.) |
| 35% | AHA | 3 | Norwegian band that won six MTV Video Music Awards for "Take On Me" (Hyph.) |
| 35% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 35% | SKYSCRAPER | 10 | Top 10 43-Across song that won the 2012 MTV "Best Video with a Message" Video Music Award |
| 34% | AHA | 3 | Norwegian band that won six MTV Video Music Awards in 1986 (Hyph.) |