| 100% | BRUCEWILLIS | 11 | "Die Hard" actor who sang the Top 10 hit "Respect Yourself" with the Pointer Sisters (2 wds.) |
| 58% | PATRICKSWAYZE | 13 | "Dirty Dancing" actor who sang the Top 10 hit "She's Like the Wind" (2 wds.) |
| 55% | EDDIEMURPHY | 11 | "Beverly Hills Cop" actor who sang the Top 10 hit "Party All the Time" (2 wds.) |
| 50% | YOUNGTHUG | 9 | "Bad Boy" rapper who cowrote the top 10 hit "Go Crazy" with Chris Brown: 2 wds. |
| 49% | KENDRICKLAMAR | 13 | Artist who had a top 10 Billboard hit with "All the Stars": 2 wds. |
| 48% | BRUCEWILLIS | 11 | Actor who made his mark as an action hero 30 years ago with the hit "Die Hard": 2 wds. |
| 47% | PATRICKSWAYZE | 13 | "Dirty Dancing" star who had a top 10 hit with "She's Like the Wind" in 1988: 2 wds. |
| 44% | DONJOHNSON | 10 | "Miami Vice" star who had a top 10 hit with "Heartbeat" in 1986: 2 wds. |
| 44% | FLORIDA | 7 | Rapper who had a top 10 hit in 2015 with "G.D.F.R.": 2 wds. |
| 43% | JACKWAGNER | 10 | "General Hospital" star who had a top 10 hit with "All I Need" in 1984: 2 wds. |
| 43% | LILWAYNE | 8 | "A Milli" rapper who's had top 10 hits in each of the last three decades: 2 wds. |
| 43% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 43% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 43% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 42% | TRAVISSCOTT | 11 | Artist who had a top 10 Billboard hit with "Stargazing": 2 wds. |
| 40% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 40% | ALICIAKEYS | 10 | Ivy Leaguer (she briefly attended Columbia) who sang the 2009 #1 hit "Empire State of Mind" with Jay Z: 2 wds. |
| 40% | ARTGARFUNKEL | 12 | Ivy Leaguer (he went to Columbia) who sang the 1970 #1 hit "Bridge Over Troubled Water" with Paul Simon: 2 wds. |
| 40% | THEPRETENDERS | 13 | Band with the 1982 Top 10 hit "Back on the Chain Gang": 2 wds. |
| 40% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 39% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 38% | ELTONJOHN | 9 | Pop star who sang a duet with Lady Gaga on his hit "Your Song" at the 2010 Grammys: 2 wds. |
| 38% | SHAWNMENDES | 11 | "Treat You Better" folk-pop singer who partnered with Justin Bieber on the 2020 top 10 song "Monster": 2 wds. |
| 37% | YOURLOVE | 8 | Only top 10 hit for 1980s British band the Outfield: 2 wds. |
| 37% | RYANGOSLING | 11 | Actor who sang "You Always Hurt the One You Love" in a movie: 2 wds. |
| 37% | FAITHHILL | 9 | September-born country singer with the Top 10 hit "This Kiss" (2 wds.) |
| 37% | MACYGRAY | 8 | September-born R&B singer with the Top 10 hit "I Try" (2 wds.) |
| 37% | POURSOME | 8 | With 20-Across, 1988 top 10 hit for Def Leppard: 2 wds. |
| 37% | TUNNELVISION | 12 | 2017 Kodak Black hit, his first in the top 10: 2 wds. |
| 36% | BARRYGIBB | 9 | September-born disco singer with the Top 10 hit "What Kind of Fool" (2 wds.) |