| 100% | SANDRABULLOCK | 13 | Actress who was EW's only two-time Entertainer of the Year, in 2009 and 2013: 2 wds. |
| 52% | BARACKOBAMA | 11 | Political victor who was Time's Person of the Year in 2008 and 2012: 2 wds. |
| 49% | JODIEFOSTER | 11 | Two-time Oscar-winning actress who was Entertainment Weekly's 1991 Entertainer of the Year: 2 wds. |
| 48% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 48% | DREWBARRYMORE | 13 | Actress who was the youngest host of "Saturday Night Live," and the only woman to host six times (2 wds.) |
| 46% | MIAWASIKOWSKA | 13 | Actress who played the daughter of 14- and 32-Across in "The Kids Are All Right": 2 wds. |
| 45% | SERENAWILLIAMS | 14 | Tennis player who won the AP Athlete of the Year award in 2002, 2009, 2013, and 2015: 2 wds. |
| 45% | COOPERKUPP | 10 | 2021 NFL Offensive Player of the Year who caught two touchdown passes in the 2022 Super Bowl for 21-Across and was named Super Bowl MVP (2 wds.) |
| 45% | THEGUARDIANS | 12 | Persecuted and endangered journalists who were Time Magazine's Persons of the Year in 2018 (2 wds.) |
| 45% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 45% | HELENHAYES | 10 | Actress who won the Emmy, Grammy, Oscar, and Tony (one of her two Oscars was for "Airport"): 2 wds. |
| 44% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 44% | POPEFRANCIS | 11 | Vatican leader who was Time's 2013 Person of the Year: 2 wds. |
| 44% | JOEYLOGANO | 10 | 2018 and 2022 NASCAR Cup Series champion who was also the NASCAR Rookie of the Year in 2009: 2 wds. |
| 44% | MEGANFOX | 8 | American actress who was in the music video of Eminem's "Love the Way You Lie": 2 wds. |
| 44% | SELMABLAIR | 10 | "Cruel Intentions" actress who was one of Glamour's 2023 Women of the Year: 2 wds. |
| 43% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 43% | RENEEZELLWEGER | 14 | "Cold Mountain" Oscar winner who was Harvard's Hasty Pudding Woman of the Year in 2009: 2 wds. |
| 43% | STANLEYTUCCI | 12 | Two time Emmy winner for his films "Winchell" and "Monk", who plays the role of Merlin, in 30a : 2 wds. |
| 43% | STEFFIGRAF | 10 | Tennis player who is the only player (man or woman) to win a Grand Slam and Olympic gold medal in one year: 2 wds. |
| 43% | KIMMULKEY | 9 | Coach of the 40-Across who is the only coach in women's college basketball to win national championships with two teams (2 wds.) |
| 42% | JENNIFERLEE | 11 | Actress who voiced Queen of Arendelle, Anna and Elsa's mother in the musical fantasy film, "Frozen": 2 wds. |
| 42% | BARACKOBAMA | 11 | 44th President of the U.S. who was awarded the Nobel Peace Prize in 2009: 2 wds. |
| 42% | ANGELAMERKEL | 12 | German chancellor who was Time Magazine's Person of the Year in 2015 (2 wds.) |
| 42% | OBAMA | 5 | Barack who was Time's Person of the Year in 2008 and 2012 |
| 42% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 41% | CHUCKCONNORS | 12 | Actor who was one of only 13 athletes to play in both the NBA and the MLB (2 wds.) |
| 41% | CATEBLANCHETT | 13 | Actress who was pregnant while filming "Indiana Jones and the Kingdom of the Crystal Skull": 2 wds. |
| 41% | EVALONGORIA | 11 | "Overboard" actress who plays Dora's mother in "Dora and the Lost City of Gold": 2 wds. |
| 41% | RUMERWILLIS | 11 | Daughter of Demi Moore and "Empire" actress who was Miss Golden Globe in 2009: 2 wds. |