| 100% | HARRYBELAFONTE | 14 | "Day-O" singer who was blacklisted for his leftist views in the Joseph McCarthy period: 2 wds. |
| 86% | CHARLIECHAPLIN | 14 | "City Lights" actor who was blacklisted for his leftist views in the Joseph McCarthy period: 2 wds. |
| 71% | ARTHUR | 6 | With 39-Across, "The Crucible" playwright who was blacklisted for his leftist views in the Joseph McCarthy period |
| 41% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 39% | CLAYAIKEN | 9 | "This Is the Night" singer who is running for Congress in North Carolina: 2 wds. |
| 39% | PAULMCCARTNEY | 13 | Singer and bass guitarist for the Beatles who was knighted in 1997: 2 wds. |
| 38% | HARRYBELAFONTE | 14 | "Day-O" singer who received the Spingarn Medal in 2012: 2 wds. |
| 37% | LENAHORNE | 9 | Jazz singer who was awarded the Spingarn Medal in 1983: 2 wds. |
| 37% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 37% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 36% | BRUNOMARS | 9 | "24K Magic" singer who was the featured act in the 2014 Super Bowl halftime show: 2 wds. |
| 36% | KATYPERRY | 9 | "Dark Horse" singer who was the featured act in the 2015 Super Bowl halftime show: 2 wds. |
| 36% | LADYGAGA | 8 | "Poker Face" singer who was the featured act in the 2017 Super Bowl halftime show: 2 wds. |
| 36% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 36% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 36% | PAULMCCARTNEY | 13 | 76-year-old singer who is still in a "Band on the Run": 2 wds. |
| 36% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 36% | JEFFLYNNE | 9 | "Evil Woman" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 36% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 36% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 36% | LEBRONJAMES | 11 | L.A. Lakers star who was named the NBA Finals MVP for the fourth time in his career in 2020 (2 wds.) |
| 36% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 35% | STEVEMILLER | 11 | "Fly Like an Eagle" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 35% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 35% | GLORIAESTEFAN | 13 | "Get On Your Feet" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 35% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 35% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 35% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 35% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 35% | ERICCLAPTON | 11 | "Layla" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 2000: 2 wds. |