| 100% | 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. |
| 49% | VISIONOF | 8 | "___ Love," song by Mariah Carey for which she won the Grammy for Best Female Pop Vocal Performance: 2 wds. |
| 41% | BLANKSPACE | 10 | Taylor Swift song that won the 2015 MTV VMA for Best Female Video: 2 wds. |
| 41% | STUCKWITH | 9 | "___ U," song by Ariana Grande and Justin Bieber (birthday today) which won an MTV Video Music Award in 2020: 2 wds. |
| 40% | UPTOWNFUNK | 10 | Mark Ronson/Bruno Mars song that won the 2015 MTV VMA for Best Male Video: 2 wds. |
| 39% | CALMDOWN | 8 | "You Need to ___," 2019 song by Taylor Swift which won the MTV Video of the Year: 2 wds. |
| 38% | HOWWILLIKNOW | 12 | Number-one hit by Whitney Houston which won the Best Female Video at the MTV Video Music Awards in 1986: 4 wds. |
| 37% | RINGS | 5 | "7 ___," number-one hit song by Ariana Grande which was nominated for Record of the Year at the 62nd Grammy Awards |
| 37% | WOMAN | 5 | "God Is a ___," hit song by Ariana Grande from her album "Sweetener" which features a monologue by Madonna in the music video |
| 36% | SUCKER | 6 | 2019 song by Jonas Brothers which won the MTV Best Pop Video |
| 36% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 36% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 36% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 36% | 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. |
| 35% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 35% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 35% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 35% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 35% | ARIANAGRANDE | 12 | Pop singer with the hit song "No Tears Left to Cry" (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% | VIVAVILLA | 9 | 1934 movie for which Wallace Beery won the best actor award at the 2nd Venice Film Festival: 2 wds. |
| 34% | ALLISONJANNEY | 13 | She won the 2018 Oscar for Best Supporting Actress for her role in "I, Tonya": 2 wds. |
| 34% | EVERYTHING | 10 | "___ She Wants," hit song by pop duo Wham! which features in the video game "GTA V" |
| 34% | TIME | 4 | "One Last ___," hit song by Ariana Grande from her album "My Everything" which stars Matt Bennett in its music video |
| 33% | 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 |
| 33% | ISME | 4 | "This ___," Keala Settle song that won the 2018 Golden Globe Award for Best Original Song: 2 wds. |
| 33% | WONDERWOMAN | 11 | Superhero film by Patty Jenkins that won the 2018 Hugo Award for Best Dramatic Presentation: 2 wds. |
| 33% | FOOFIGHTERS | 11 | Band whose "Run" won the 2018 Grammy for Best Rock Song: 2 wds. |
| 33% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 33% | FLY | 3 | "Learning to ___," Pink Floyd song that won Best Concept Video at the MTV Video Music Awards |