| 100% | HOWWILLIKNOW | 12 | Number-one hit by Whitney Houston which won the Best Female Video at the MTV Video Music Awards in 1986: 4 wds. |
| 40% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 39% | NOTEARS | 7 | "___ Left to Cry," hit song by Ariana Grande for which she won the 2018 Best Pop Video at the MTV VMAs: 2 wds. |
| 39% | 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. |
| 39% | FLY | 3 | "Learning to ___," Pink Floyd song that won Best Concept Video at the MTV Video Music Awards |
| 38% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 37% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 37% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 37% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 36% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 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% | WITHSOMEBODY | 12 | "I Wanna Dance ___ (Who Loves Me)," number-one hit by Whitney Houston that was featured in the film "13 Going on 30": 2 wds. |
| 36% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 36% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 35% | STUCKWITH | 9 | "___ U," song by Ariana Grande and Justin Bieber (birthday today) which won an MTV Video Music Award in 2020: 2 wds. |
| 35% | ONEDIRECTION | 12 | Boy band that was the Best New Artist at the 2012 MTV Video Music Awards: 2 wds. |
| 35% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 34% | ALWAYSLOVEYOU | 13 | "I Will ___," number-one hit by Whitney Houston recorded for "The Bodyguard" which is a cover of a Dolly Parton song: 3 wds. |
| 34% | SLEDGEHAMMER | 12 | Song that accounted for 9 of the 10 MTV Video Music Awards won by 17-Across in 1987 |
| 34% | COUNTRYFOROLD | 13 | "No ___ Men," a movie in which Javier Bardem starred in and won the Best Actor Award at the Oscars for his performance: 3 wds. |
| 33% | AHA | 3 | Norwegian band that won six MTV Video Music Awards in 1986 (Hyph.) |
| 33% | AHA | 3 | Norwegian band that won eight MTV Video Music Awards in 1986: Hyph. |
| 33% | COLDPLAY | 8 | "Orphans" band who won Best Rock at the 2020 MTV Video Music Awards |
| 33% | SKYFALL | 7 | Hit song by Adele from a James Bond movie which won the Academy Award for Best Original Song in 2013 |
| 33% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 32% | YOUMIGHTTHINK | 13 | 1984 hit by the Cars that won the first MTV Video of the Year: 3 wds |
| 32% | TIMBERLAKE | 10 | Justin ___, singer who won Video of the Year for "Mirrors" at MTV Video Music Awards in 2013 |
| 32% | KATY | 4 | Singer ___ Perry who won Video of the Year Award for "Firework" at MTV Video Music Awards in 2011 |
| 32% | PORKANDBEANS | 12 | Single by 42-Across whose video won a Grammy Award for Best Music Video in 2009 (3 wds.) |
| 32% | BADROMANCE | 10 | A 2009 hit by Lady Gaga which won two Grammys and has gone on to become one of the best selling singles of all time: 2 wds |