| 100% | LLCOOLJ | 7 | Actor and rapper who turned 50 on January 14, 2018 (3 wds.) |
| 54% | PATTONOSWALT | 12 | Comedian/actor of 14-Across and 29-Across who turned 50 on January 27, 2019 (2 wds.) |
| 51% | DANIELCRAIG | 11 | "Skyfall" actor who turned 50 on March 2, 2018 (2 wds.) |
| 48% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who turns 50 on October 12, 2018 (2 wds.) |
| 48% | SEANCOMBS | 9 | Rapper who turned 50 on November 4, 2019 (2 wds.) |
| 46% | CLINTEASTWOOD | 13 | Actor and director who turns 90 on May 31, 2020 (2 wds.) |
| 46% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 46% | MOLLYRINGWALD | 13 | "Sixteen Candles" actress who turned 50 on February 18, 2018 (2 wds.) |
| 43% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who turned 50 years old on January 30, 2024 (2 wds.) |
| 42% | TINAFEY | 7 | Multi-award-winning comic, actor, writer, and producer who turned 50 on May 18, 2020 (2 wds.) |
| 42% | OZZYOSBOURNE | 12 | Rock music icon and reality TV star who turned 70 on December 3, 2018 (2 wds.) |
| 42% | BILLYCRYSTAL | 12 | 14-Across, 19-Across, and 36-Across actor and comedian who turned 75 on March 14, 2023 (2 wds.) |
| 41% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 41% | ROWANATKINSON | 13 | "Mr. Bean" actor who turned 65 on January 6th (2 wds.) |
| 41% | ROBERTPATRICK | 13 | "Scorpion" actor who turns 60 on November 5, 2018 (2 wds.) |
| 41% | MATTHEWPERRY | 12 | Actor who played 14-Across and 25-Across who turns 50 years old today (2 wds.) |
| 41% | STEFFIGRAF | 10 | Hall of Fame tennis great who turned 50 on June 14, 2019 (2 wds.) |
| 40% | KENGRIFFEYJR | 12 | Baseball Hall of Famer who turned 50 on November 21, 2019 (3 wds.) |
| 38% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 37% | MIKEPIAZZA | 10 | MLB Hall of Famer who turns 50 in 2018 (2 wds.) |
| 37% | BARRYSANDERS | 12 | NFL Hall of Famer who turns 50 in 2018 (2 wds.) |
| 37% | GARYPAYTON | 10 | NBA Hall of Famer who turns 50 in 2018 (2 wds.) |
| 37% | VINDIESEL | 9 | "The Fate of the Furious" actor who turned 50 on July 18, 2017 (2 wds.) |
| 37% | RALPHFIENNES | 12 | Actor born December 22, 1962, who played 14-Across and 29-Across, and who plays Moriarty in 2018's "Holmes & Watson" (2 wds.) |
| 36% | MARIOLOPEZ | 10 | 16-Across and 34-Across star who turned 50 on October 10, 2023 (2 wds.) |
| 35% | FAITHHILL | 9 | "This Kiss" country singer who turns 50 on September 21, 2017 (2 wds.) |
| 35% | DOUGRAYSCOTT | 12 | "Taken 3" actor who plays Kate's father Jacob on 14-Across: 2 wds. |
| 35% | PAULRUDD | 8 | "Ant-Man" and 15-Across, 22-Across, and 37-Across actor who turns 50 on April 6 (2 wds.) |
| 34% | STEVEBURNS | 10 | 17-Across and 28-Across host/musician who turns 50 on October 9, 2023 (2 wds.) |
| 34% | NICKIMINAJ | 10 | Rapper who sings "Barbie World" with Ice Spice and Aqua on "Barbie: The Album" (2 wds.) |