| 100% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 69% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 56% | RAYCHARLES | 10 | "Hit the Road Jack" singer who has a solo in 1985's "We Are the World": 2 wds. |
| 52% | PATRICKSWAYZE | 13 | "Dirty Dancing" star who had a top 10 hit with "She's Like the Wind" in 1988: 2 wds. |
| 49% | DONJOHNSON | 10 | "Miami Vice" star who had a top 10 hit with "Heartbeat" in 1986: 2 wds. |
| 49% | THEBEACHBOYS | 12 | "Good Vibrations" group who had a hit in 1963 with "Surfin' U.S.A.": 3 wds. |
| 48% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 47% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 47% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 46% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 46% | FLORIDA | 7 | Rapper who had a top 10 hit in 2015 with "G.D.F.R.": 2 wds. |
| 46% | TIMBERLAKE | 10 | Justin ___, a singer famous for his hit single "Cry Me a River", who starred in the film "Friends with Benefits": 2 wds. |
| 45% | TINATURNER | 10 | "Private Dancer" singer who has a solo in "We Are the World": 2 wds. |
| 45% | RODSTEWART | 10 | British singer/songwriter who had a Top 20 hit with his version of "Forever Young" in 1988 (2 wds.) |
| 45% | DIONNEWARWICK | 13 | "Walk On By" singer who has a solo in "We Are the World": 2 wds. |
| 45% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 44% | JACKWAGNER | 10 | "General Hospital" star who had a top 10 hit with "All I Need" in 1984: 2 wds. |
| 43% | KATYPERRY | 9 | "Roar" singer who had a guest appearance in "HIMYM" in the episode "Oh Honey" : 2 wds. |
| 43% | TIGERWOODS | 10 | Golfer who won the 2008 U.S. Open with a double fracture in his tibia: 2 wds. |
| 43% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |
| 43% | NICKIMINAJ | 10 | "Anaconda" singer who has lived in both Trinidad and the US: 2 wds. |
| 43% | BRITNEYSPEARS | 13 | Singer with the 2001 hit "I'm a Slave 4 U": 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% | SEANKINGSTON | 12 | "Beautiful Girls" singer who has lived in both Jamaica and the US: 2 wds. |
| 43% | KENDRICKLAMAR | 13 | Artist who had a top 10 Billboard hit with "All the Stars": 2 wds. |
| 42% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 42% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 42% | ZENDAYA | 7 | Singer who had a hit with Rewrite the Stars |
| 42% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |