| 100% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 75% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 75% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 53% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 51% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 49% | ANGELAMERKEL | 12 | German chancellor who was Time Magazine's Person of the Year in 2015 (2 wds.) |
| 49% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 49% | AARONJUDGE | 10 | New York Yankees outfielder who was the Associated Press Athlete of the Year in 2022: 2 wds. |
| 49% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 48% | CHINEYOGWUMIKE | 14 | Nigerian American WNBA player who was named Rookie of the Year in 2014: 2 wds. |
| 48% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 48% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 48% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 48% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 47% | GRETATHUNBERG | 13 | Swedish environmental activist who was Time Magazine's Person of the Year in 2019 (2 wds.) |
| 47% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 47% | JEFFLYNNE | 9 | "Evil Woman" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 47% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 46% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 46% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 46% | STEVEMILLER | 11 | "Fly Like an Eagle" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 46% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 46% | GLORIAESTEFAN | 13 | "Get On Your Feet" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 46% | THEGUARDIANS | 12 | Persecuted and endangered journalists who were Time Magazine's Persons of the Year in 2018 (2 wds.) |
| 46% | IGASWIATEK | 10 | Polish tennis player who won WTA Player of the Year in 2022 and 2023: 2 wds. |
| 46% | JONIMITCHELL | 12 | "Both Sides Now" singer-songwriter who wrote "Morning Glory on the Vine," a book of poetry and drawings (2 wds.) |
| 46% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 46% | ERICCLAPTON | 11 | "Layla" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 2000: 2 wds. |
| 46% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 46% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |