| 100% | JODIEFOSTER | 11 | Two-time Oscar-winning actress who was Entertainment Weekly's 1991 Entertainer of the Year: 2 wds. |
| 56% | SANDRABULLOCK | 13 | Actress who was EW's only two-time Entertainer of the Year, in 2009 and 2013: 2 wds. |
| 54% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 52% | JODIEFOSTER | 11 | Actress who won her second Oscar, for 1991's "The Silence of the Lambs," at age 29: 2 wds. |
| 46% | SELMABLAIR | 10 | "Cruel Intentions" actress who was one of Glamour's 2023 Women of the Year: 2 wds. |
| 46% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 45% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 45% | KEVINDURANT | 11 | 2008 NBA Rookie of the Year (with the SuperSonics) who has won two championship rings: 2 wds. |
| 45% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 45% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 45% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 45% | VLADIMIRPUTIN | 13 | Russian leader who was Time's 2007 Person of the Year: 2 wds. |
| 45% | DONALDTRUMP | 11 | US leader who was Time's 2016 Person of the Year: 2 wds. |
| 45% | POPEFRANCIS | 11 | Vatican leader who was Time's 2013 Person of the Year: 2 wds. |
| 45% | GRETATHUNBERG | 13 | Teen activist who was Time's 2019 Person of the Year: 2 wds. |
| 44% | AUDREYHEPBURN | 13 | Actress who won the Emmy, Grammy, Oscar, and Tony (the Oscar was for "Roman Holiday"): 2 wds. |
| 44% | JESSICALANGE | 12 | Two-time Oscar-winning actress who starred in the 1976 movie "King Kong": 2 wds. |
| 44% | KATEUPTON | 9 | "The Other Woman" actress who's been on the cover of the Sports Illustrated Swimsuit Issue four times: 2 wds. |
| 44% | LIONELMESSI | 11 | Inter Miami captain who was Time's 2023 Athlete of the Year: 2 wds. |
| 44% | CAITLINCLARK | 12 | Indiana Fever player who was Time's 2024 Athlete of the Year: 2 wds. |
| 43% | RITAMORENO | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (the Oscar was for "West Side Story"): 2 wds. |
| 43% | ELLENBURSTYN | 12 | "Interstellar" actress who has won the Triple Crown of Acting (Emmy, Oscar, and Tony): 2 wds. |
| 43% | DREWBREES | 9 | Quarterback who was Sports Illustrated's 2010 Sportsman of the Year: 2 wds. |
| 43% | SIMONEBILES | 11 | Most decorated American gymnast who was Time's 2021 Athlete of the Year: 2 wds. |
| 42% | ANNEHATHAWAY | 12 | "Les Misérables" actress who won an Oscar for her performance, despite only 15 minutes of screen time: 2 wds. |
| 42% | CHARLIZETHERON | 14 | "Monster" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2008: 2 wds. |
| 42% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 42% | HELENMIRREN | 11 | "The Queen" actress who was the unseen narrator of 2023's "Barbie": 2 wds. |
| 42% | NOVAKDJOKOVIC | 13 | Serbian tennis star who's been ATP Player of the Year a record eight times: 2 wds. |
| 42% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |