| 100% | CALMDOWN | 8 | "You Need to ___," 2019 song by Taylor Swift which won the MTV Video of the Year: 2 wds. |
| 59% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 58% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |
| 51% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 51% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 51% | 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. |
| 51% | SUCKER | 6 | 2019 song by Jonas Brothers which won the MTV Best Pop Video |
| 50% | 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. |
| 49% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 48% | BLANKSPACE | 10 | Taylor Swift song that won the 2015 MTV VMA for Best Female Video: 2 wds. |
| 48% | FOLKLORE | 8 | Album by Taylor Swift which won the Grammy for Album of the Year in 2021 |
| 47% | STILLFALLING | 12 | "___ for You," 2016 song by Ellie Goulding which is a part of the soundtrack to the film "Bridget Jones's Baby": 2 wds. |
| 44% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 44% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 43% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 43% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 43% | BEATINGHEART | 12 | 2014 song by Ellie Goulding which is a part of the soundtrack to the film "Divergent": 2 wds. |
| 43% | LOVER | 5 | 2019 album by Taylor Swift featuring the hits "Me!" and "You Need to Calm Down" |
| 43% | CALMDOWN | 8 | "You Need To ___," Taylor Swift song: 2 wds. |
| 42% | YOUMIGHTTHINK | 13 | 1984 hit by the Cars that won the first MTV Video of the Year: 3 wds |
| 42% | TOWNROAD | 8 | "Old ___," 2019 song by Lil Nas X that is one of the shortest songs to enter the Billboard charts: 2 wds. |
| 42% | ALLI | 4 | "___ Want For Christmas is You," song by Mariah Carey that topped the charts after 25 years of its release: 2 wds. |
| 42% | TAYLORSWIFT | 11 | "You Need to Calm Down" singer who won six 2019 American Music Awards, including Artist of the Decade (2 wds.) |
| 41% | BACK | 4 | "___ To December," 2010 song by Taylor Swift whose title means the opposite of "front" |
| 41% | COUNTRY | 7 | ___ Music Association Awards, ceremony at which Taylor Swift became the youngest person to win Entertainer of the Year |
| 41% | YOUMIGHTTHINK | 13 | The Cars Top 10 hit whose video features 44-Across as a housefly (and was the first to win the MTV Video Music Award for Video of the Year) (3 wds.) |
| 41% | WITHLUV | 7 | "Boy ___," song by BTS featuring Halsey which was the most viewed music video in 24 hours in 2019: 2 wds. |
| 40% | THIS | 4 | "___ is America," hit song by Childish Gambino which won the Grammy for Record of the Year |
| 40% | NAOMIOSAKA | 10 | Japanese tennis player who won the Laureus Breakthrough of the Year award in 2019: 2 wds. |
| 40% | NOVAKDJOKOVIC | 13 | Serbian tennis player who won the Laureus Sportsman of the Year award in 2019: 2 wds. |