| 100% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 65% | BLANKSPACE | 10 | Taylor Swift song that won the 2015 MTV VMA for Best Female Video: 2 wds. |
| 63% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |
| 62% | UPTOWNFUNK | 10 | Mark Ronson/Bruno Mars song that won the 2015 MTV VMA for Best Male Video: 2 wds. |
| 53% | CALMDOWN | 8 | "You Need to ___," 2019 song by Taylor Swift which won the MTV Video of the Year: 2 wds. |
| 51% | ANACONDA | 8 | Nicki Minaj song that won the 2015 MTV VMA for Best Hip-Hop Video |
| 46% | LEAVETHE | 8 | With 32-Across, Silk Sonic single that won the 2022 Grammy for Song of the Year: 2 wds. |
| 45% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 45% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 44% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year 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.) |
| 43% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 43% | 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. |
| 43% | 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 |
| 41% | KILLBILL | 8 | SZA #1 hit that won the 2023 BET Video of the Year Award: 2 wds. |
| 41% | YOUMIGHTTHINK | 13 | 1984 hit by the Cars that won the first MTV Video of the Year: 3 wds |
| 41% | 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.) |
| 41% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 40% | JUSTLIKETHAT | 12 | Bonnie Raitt single that won the 2023 Grammy for Song of the Year: 3 wds. |
| 40% | ICANTBREATHE | 12 | H.E.R. single that won the 2021 Grammy for Song of the Year: 3 wds. |
| 40% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 40% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 39% | WEAREYOUNG | 10 | #1 fun. hit released in 2011 that won the Grammy for Song of the Year: 3 wds. |
| 39% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 39% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 38% | SLEDGEHAMMER | 12 | Song that accounted for 9 of the 10 MTV Video Music Awards won by 17-Across in 1987 |
| 38% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 38% | 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.) |
| 38% | JUICE | 5 | Song from 46-Across's album "Cuz I Love You" that won the 2019 Soul Train Music Award for Video of the Year |
| 38% | ALLI | 4 | "___ Want For Christmas is You," song by Mariah Carey that topped the charts after 25 years of its release: 2 wds. |