| 100% | DANIELCRAIG | 11 | "Skyfall" actor who turned 50 on March 2, 2018 (2 wds.) |
| 74% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who turns 50 on October 12, 2018 (2 wds.) |
| 68% | LLCOOLJ | 7 | Actor and rapper who turned 50 on January 14, 2018 (3 wds.) |
| 65% | ROBERTPATRICK | 13 | "Scorpion" actor who turns 60 on November 5, 2018 (2 wds.) |
| 63% | MOLLYRINGWALD | 13 | "Sixteen Candles" actress who turned 50 on February 18, 2018 (2 wds.) |
| 63% | VINDIESEL | 9 | "The Fate of the Furious" actor who turned 50 on July 18, 2017 (2 wds.) |
| 61% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 60% | TINAFEY | 7 | Multi-award-winning comic, actor, writer, and producer who turned 50 on May 18, 2020 (2 wds.) |
| 59% | BILLYCRYSTAL | 12 | 14-Across, 19-Across, and 36-Across actor and comedian who turned 75 on March 14, 2023 (2 wds.) |
| 59% | PAULRUDD | 8 | "Ant-Man" and 15-Across, 22-Across, and 37-Across actor who turns 50 on April 6 (2 wds.) |
| 56% | RONHOWARD | 9 | Actor/director who turns 70 years old on March 1, 2024 (2 wds.) |
| 55% | PATTONOSWALT | 12 | Comedian/actor of 14-Across and 29-Across who turned 50 on January 27, 2019 (2 wds.) |
| 54% | SEANCOMBS | 9 | Rapper who turned 50 on November 4, 2019 (2 wds.) |
| 54% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 54% | ROBKARDASHIAN | 13 | Reality TV star who turned 30 on March 17, 2017 (2 wds.) |
| 53% | TYLERHOECHLIN | 13 | Teen heartthrob actor who turns 30 on September 11, 2017 (2 wds.) |
| 53% | FAITHHILL | 9 | "This Kiss" country singer who turns 50 on September 21, 2017 (2 wds.) |
| 53% | ROWANATKINSON | 13 | "Mr. Bean" actor who turned 65 on January 6th (2 wds.) |
| 53% | STEFFIGRAF | 10 | Hall of Fame tennis great who turned 50 on June 14, 2019 (2 wds.) |
| 52% | CLINTEASTWOOD | 13 | Actor and director who turns 90 on May 31, 2020 (2 wds.) |
| 52% | OLIVIAWILDE | 11 | "Don't Worry Darling" director/actress who turned 40 on March 10, 2024 (2 wds.) |
| 52% | MARIOLOPEZ | 10 | 16-Across and 34-Across star who turned 50 on October 10, 2023 (2 wds.) |
| 52% | ELTONJOHN | 9 | Legendary musician born Reginald Kenneth Dwight who turns 75 on March 25, 2022 (2 wds.) |
| 52% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 52% | MIKEPIAZZA | 10 | MLB Hall of Famer who turns 50 in 2018 (2 wds.) |
| 52% | BARRYSANDERS | 12 | NFL Hall of Famer who turns 50 in 2018 (2 wds.) |
| 52% | GARYPAYTON | 10 | NBA Hall of Famer who turns 50 in 2018 (2 wds.) |
| 52% | TIMMCGRAW | 9 | "Just to See You Smile" country singer who turned 50 on May 1, 2017 (2 wds.) |
| 52% | STEVEBURNS | 10 | 17-Across and 28-Across host/musician who turns 50 on October 9, 2023 (2 wds.) |
| 51% | JEFFFOXWORTHY | 13 | Blue Collar Comedy Tour comedian who turns 60 on September 6, 2018 (2 wds.) |