| 100% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 80% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 79% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 54% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 54% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 52% | ANGELAMERKEL | 12 | German chancellor who was Time Magazine's Person of the Year in 2015 (2 wds.) |
| 52% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 51% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 51% | CHINEYOGWUMIKE | 14 | Nigerian American WNBA player who was named Rookie of the Year in 2014: 2 wds. |
| 51% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 50% | GRETATHUNBERG | 13 | Swedish environmental activist who was Time Magazine's Person of the Year in 2019 (2 wds.) |
| 50% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 50% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 50% | JEFFLYNNE | 9 | "Evil Woman" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 50% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 50% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 49% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 49% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 49% | STEVEMILLER | 11 | "Fly Like an Eagle" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 49% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 49% | GLORIAESTEFAN | 13 | "Get On Your Feet" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 49% | THEGUARDIANS | 12 | Persecuted and endangered journalists who were Time Magazine's Persons of the Year in 2018 (2 wds.) |
| 49% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 49% | ERICCLAPTON | 11 | "Layla" guitarist and singer who was inducted into the Rock and Roll Hall of Fame in 2000: 2 wds. |
| 49% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 49% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 49% | JOEYLOGANO | 10 | 2018 and 2022 NASCAR Cup Series champion who was also the NASCAR Rookie of the Year in 2009: 2 wds. |
| 49% | EARTHAKITT | 10 | "Santa Baby" singer who was the voice of villainous Yzma in Disney's "The Emperor's New Groove": 2 wds. |
| 49% | LINDARONSTADT | 13 | "You're No Good" singer who was inducted into the Rock and Roll Hall of Fame in 2014: 2 wds. |
| 49% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |