| 100% | JOHNLEGEND | 10 | Singer with the 2020 love song "Bigger Love" (2 wds.) |
| 89% | DEMILOVATO | 10 | Singer with the 2020 love song "I Love Me" (2 wds.) |
| 85% | JUSTINBIEBER | 12 | Singer with the 2020 love song "That's What Love Is" (2 wds.) |
| 76% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 76% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 68% | ARIANAGRANDE | 12 | "7 Rings" pop singer who partnered with Justin Bieber on the 2020 #1 song "Stuck With U": 2 wds. |
| 67% | LEWISCAPALDI | 12 | Scottish singer with the 2019 hit "Someone You Loved": 2 wds. |
| 67% | SHAWNMENDES | 11 | "Treat You Better" folk-pop singer who partnered with Justin Bieber on the 2020 top 10 song "Monster": 2 wds. |
| 64% | VANMORRISON | 11 | Rock singer with the 1971 song "Wild Night": 2 wds. |
| 64% | KIDROCK | 7 | Rap and country singer with the song "Bawitdaba": 2 wds. |
| 64% | GARTHBROOKS | 11 | "Friends in Low Places" singer/songwriter honored with the 2020 Gershwin Prize for Popular Song (2 wds.) |
| 63% | BILLWITHERS | 11 | Singer with the 1971 song "Ain't No Sunshine": 2 wds. |
| 63% | ERICCLAPTON | 11 | "I Shot the Sheriff" singer with the 1992 song "Tears in Heaven": 2 wds. |
| 63% | SELENAGOMEZ | 11 | "Lose You to Love Me" singer with the beauty brand Rare Beauty: 2 wds. |
| 62% | STEVIEWONDER | 12 | Singer with four No. 1 songs in the 1980s, including "I Just Called To Say I Love You" (2 wds.) |
| 61% | STEVIEWONDER | 12 | Singer with four #1 songs in the 1980s, including "I Just Called to Say I Love You" (2 wds.) |
| 61% | BARRYWHITE | 10 | Singer with the 1974 hit "Can't Get Enough of Your Love, Babe": 2 wds. |
| 61% | PETERFRAMPTON | 13 | "I'm in You" singer with the hit single "Baby, I Love Your Way": 2 wds. |
| 60% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 60% | IGGYAZALEA | 10 | Featured singer on the buttocks-themed song "Booty" with Jennifer Lopez: 2 wds. |
| 59% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 59% | NATALIECOLE | 11 | R&B singer with the hits "Our Love" and "Miss You Like Crazy" (1950-2015): 2 wds. |
| 59% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 58% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 58% | BARRYMANILOW | 12 | Singer with the 1974 single "Mandy": 2 wds. |
| 58% | TINATURNER | 10 | "What's Love Got to Do With It" singer who performed the theme to "GoldenEye": 2 wds. |
| 57% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 57% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 57% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 57% | DOLLYPARTONS | 12 | With 27-Across, Netflix anthology series dramatizing the stories behind some of a singer's songs: 2 wds. |