| 100% | SLEDGEHAMMER | 12 | Song that accounted for 9 of the 10 MTV Video Music Awards won by 17-Across in 1987 |
| 50% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 47% | 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 |
| 44% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 43% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 39% | 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% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 38% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 36% | BLACKPINK | 9 | "How You Like That" band who won Song of Summer at the 2020 MTV Video Music Awards |
| 36% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |
| 36% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 36% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 36% | AHA | 3 | Band that won six MTV Video Music Awards for "Take On Me" in 1986 (Hyph.) |
| 36% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 36% | IRREPLACEABLE | 13 | Beyoncé hit song that won the Soul Train Music Award for Best R&B/Soul Single in 2007 |
| 36% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 36% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 35% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 35% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 35% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 35% | TIMBERLAKE | 10 | Justin ___, singer who won Video of the Year for "Mirrors" at MTV Video Music Awards in 2013 |
| 35% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |
| 35% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 34% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 34% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 34% | KATY | 4 | Singer ___ Perry who won Video of the Year Award for "Firework" at MTV Video Music Awards in 2011 |
| 34% | SOBER | 5 | 1993 song by the rock band Tool that features stop-motion animation of a humanoid in the official music video |
| 34% | GAGA | 4 | Lady ___, singer who won the Video of the Year for "Bad Romance" at MTV Video Music Awards in 2011 |
| 34% | SKYSCRAPER | 10 | Top 10 43-Across song that won the 2012 MTV "Best Video with a Message" Video Music Award |
| 34% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |