| 100% | DIXIEDAMELIO | 12 | TikTok star and singer with the 2021 hit "Psycho": 2 wds. |
| 62% | OLIVIARODRIGO | 13 | Singer with the 2021 hit "Good 4 U": 2 wds. |
| 58% | BABYARIEL | 9 | TikTok star and singer who appeared in the Disney Channel movie "Zombies 2": 2 wds. |
| 57% | LORENGRAY | 9 | TikTok star and singer who appeared in the video for Taylor Swift's "The Man": 2 wds. |
| 57% | OLIVIARODRIGO | 13 | Former Disney Channel star with the 2021 #1 hits "Drivers License" and "Good 4 U": 2 wds. |
| 55% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 54% | NATALIECOLE | 11 | R&B singer with the hits "Our Love" and "Miss You Like Crazy" (1950-2015): 2 wds. |
| 51% | SINEADOCONNOR | 13 | Singer with the 1990 hit "Nothing Compares 2 U": 2 wds. |
| 51% | LISALOEB | 8 | Singer with the 1994 hit "Stay (I Missed You)": 2 wds. |
| 51% | TAYLORDAYNE | 11 | Singer with the 1988 hit "Don't Rush Me": 2 wds. |
| 51% | JOHNNYCASH | 10 | Country singer with the hits 17-Across, 29-Across, and "A Boy Named Sue" (2 wds.) |
| 51% | KANEBROWN | 9 | R&B and country singer with the 2022 country hit "Thank God": 2 wds. |
| 50% | RACHELPLATTEN | 13 | Singer with the 2015 hit "Stand by You": 2 wds. |
| 50% | CALVINHARRIS | 12 | Scottish singer with the 2014 hit "Summer": 2 wds. |
| 50% | CAMILACABELLO | 13 | Cuban-American singer with the 2018 #1 hit "Havana": 2 wds. |
| 49% | BENEKING | 8 | Singer with the 1961 and 1986 hit "Stand by Me": 3 wds. |
| 49% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 49% | BOBBYMCFERRIN | 13 | Singer with the 1988 hit "Don't Worry, Be Happy": 2 wds. |
| 49% | SELENAGOMEZ | 11 | "Wizards of Waverly Place" star and singer with a fashion line at Kmart: 2 wds. |
| 49% | BRITNEYSPEARS | 13 | Singer with the 2001 hit "I'm a Slave 4 U": 2 wds. |
| 49% | LEWISCAPALDI | 12 | Scottish singer with the 2019 hit "Someone You Loved": 2 wds. |
| 49% | VANESSACARLTON | 14 | American singer with the 2002 hit "A Thousand Miles": 2 wds. |
| 49% | SHAWNMENDES | 11 | Canadian pop singer with the 2015 hit "Stitches": 2 wds. |
| 48% | JOSEFELICIANO | 13 | Puerto Rican singer with the perennial holiday hit "Feliz Navidad": 2 wds. |
| 48% | BARRYWHITE | 10 | Singer with the 1974 hit "Can't Get Enough of Your Love, Babe": 2 wds. |
| 48% | MICHAELJACKSON | 14 | Singer with the most #1 Billboard Hot 100 hits (9) during the 1980s: 2 wds. |
| 48% | CHAPPELLROAN | 12 | Singer with the debut album "The Rise and Fall of a Midwest Princess": 2 wds. |
| 48% | JACKSONBROWNE | 13 | "Running on Empty" singer with the hit single "Somebody's Baby": 2 wds. |
| 48% | JOHNNYCASH | 10 | Country singer with the 1969 crossover hit "A Boy Named Sue": 2 wds. |
| 48% | PATSYCLINE | 10 | Country singer with the 1961 crossover hit "I Fall to Pieces": 2 wds. |