| 100% | DEMILOVATO | 10 | 18-Across and 31-Across singer nominated for nine MTV Video Music Awards (2 wds.) |
| 62% | CAMILACABELLO | 13 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 18-Across (2 wds.) |
| 56% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 56% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 56% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 55% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 55% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 55% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 55% | SHAWNMENDES | 11 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 32-Across (2 wds.) |
| 54% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 54% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 54% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 54% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 53% | 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.) |
| 52% | 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.) |
| 52% | WATER | 5 | "Cold ___," song by Major Lazer featuring Justin Bieber and MO which was nominated for an MTV Video Music award in 2017 |
| 52% | SORRYNOTSORRY | 13 | Top 10 43-Across song nominated for the 2017 MTV "Song of Summer" Video Music Award and the 2018 MTV "Best Pop Video" Video Music Award (3 wds.) |
| 49% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 48% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 48% | THEKILLERS | 10 | 18-Across and 31-Across rock band that has been nominated for seven Grammys since 2005 (2 wds.) |
| 47% | STUCKWITH | 9 | "___ U," song by Ariana Grande and Justin Bieber (birthday today) which won an MTV Video Music Award in 2020: 2 wds. |
| 47% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 46% | JULIAMICHAELS | 13 | Singer/songwriter nominated for the 2017 American Music Award for New Artist of the Year (2 wds.) |
| 46% | 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. |
| 45% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 45% | KEKEPALMER | 10 | "Scream Queens" actress who hosted the socially distant 2020 MTV Video Music Awards: 2 wds. |
| 45% | ALICIAKEYS | 10 | 18-Across and 31-Across singer-songwriter who was born January 25, 1981 (2 wds.) |
| 45% | ELLIEGOULDING | 13 | 15-Across and 29-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 45% | ELLIEGOULDING | 13 | 14-Across and 45-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 45% | LADYGAGA | 8 | "Rain on Me" singer who won the MTV Tricon Award, Artist of the Year, and two other awards at the 2020 MTV Video Music Awards (2 wds.) |