| 100% | TINAFEY | 7 | Multi-award-winning comic, actor, writer, and producer who turned 50 on May 18, 2020 (2 wds.) |
| 53% | CLINTEASTWOOD | 13 | Actor and director who turns 90 on May 31, 2020 (2 wds.) |
| 42% | SEANPENN | 8 | Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
| 42% | LLCOOLJ | 7 | Actor and rapper who turned 50 on January 14, 2018 (3 wds.) |
| 41% | VINDIESEL | 9 | "The Fate of the Furious" actor who turned 50 on July 18, 2017 (2 wds.) |
| 41% | DANIELCRAIG | 11 | "Skyfall" actor who turned 50 on March 2, 2018 (2 wds.) |
| 39% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 39% | MOLLYRINGWALD | 13 | "Sixteen Candles" actress who turned 50 on February 18, 2018 (2 wds.) |
| 38% | TIMMCGRAW | 9 | "Just to See You Smile" country singer who turned 50 on May 1, 2017 (2 wds.) |
| 36% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who turns 50 on October 12, 2018 (2 wds.) |
| 35% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 34% | SEANCOMBS | 9 | Rapper who turned 50 on November 4, 2019 (2 wds.) |
| 34% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 34% | PATTONOSWALT | 12 | Comedian/actor of 14-Across and 29-Across who turned 50 on January 27, 2019 (2 wds.) |
| 34% | TOMCRUISE | 9 | Actor and producer who plays Ethan Hunt in the "Mission: Impossible" series: 2 wds. |
| 34% | SAMSHEPARD | 10 | Writer, actor, and director who won a Pulitzer Prize for the play "Buried Child" (2 wds.) |
| 34% | NORMMACDONALD | 13 | "SNL" actor and comedian who won $500,000 for charity on "Who Wants to Be a Millionaire" in 2000: 2 wds. |
| 33% | SAMSHEPARD | 10 | Award-winning writer, actor, and director born November 5, 1943 (2 wds.) |
| 33% | PAULGIAMATTI | 12 | "Cinderella Man" and "Sideways" actor who turned down the role of Michael Scott on "The Office": 2 wds. |
| 33% | MARIOLOPEZ | 10 | 16-Across and 34-Across star who turned 50 on October 10, 2023 (2 wds.) |
| 33% | JULIANFELLOWES | 14 | 18-Across and 44-Across writer/creator who won an Academy Award for Best Original Screenplay for "Gosford Park" (2 wds.) |
| 33% | MICHAELJFOX | 11 | Actor who won Emmys for his roles on "Rescue Me," "Spin City," and "Family Ties": 3 wds. |
| 32% | FAITHHILL | 9 | "This Kiss" country singer who turns 50 on September 21, 2017 (2 wds.) |
| 32% | MARIKOTAMAKI | 12 | Writer/artist who won the 2020 Eisner Award for Best Writer for the comics series "Harley Quinn: Breaking Glass," "Laura Dean Keeps Breaking Up with Me," and "Archie" (2 wds.) |
| 32% | LADYGAGA | 8 | "Rain on Me" singer who won the MTV Tricon Award, Artist of the Year, and two other awards at the 2020 MTV Video Music Awards (2 wds.) |
| 32% | DANIELKALUUYA | 13 | "Judas and the Black Messiah" actor who won the 2020 Golden Globe Award for Best Supporting Actor - Motion Picture (2 wds.) |
| 32% | QUINCYJONES | 11 | "Thriller" producer who won the 1982, 1984, and 1991 Grammys for Producer of the Year, Non-Classical: 2 wds. |
| 32% | STEVEBURNS | 10 | 17-Across and 28-Across host/musician who turns 50 on October 9, 2023 (2 wds.) |
| 32% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who turned 50 years old on January 30, 2024 (2 wds.) |
| 32% | STEFFIGRAF | 10 | Hall of Fame tennis great who turned 50 on June 14, 2019 (2 wds.) |