| 100% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who turns 50 on October 12, 2018 (2 wds.) |
| 63% | DANIELCRAIG | 11 | "Skyfall" actor who turned 50 on March 2, 2018 (2 wds.) |
| 54% | VINDIESEL | 9 | "The Fate of the Furious" actor who turned 50 on July 18, 2017 (2 wds.) |
| 51% | LLCOOLJ | 7 | Actor and rapper who turned 50 on January 14, 2018 (3 wds.) |
| 50% | MOLLYRINGWALD | 13 | "Sixteen Candles" actress who turned 50 on February 18, 2018 (2 wds.) |
| 49% | PAULGIAMATTI | 12 | "Cinderella Man" and "Sideways" actor who turned down the role of Michael Scott on "The Office": 2 wds. |
| 49% | ROBERTPATRICK | 13 | "Scorpion" actor who turns 60 on November 5, 2018 (2 wds.) |
| 49% | PAULRUDD | 8 | "Ant-Man" and 15-Across, 22-Across, and 37-Across actor who turns 50 on April 6 (2 wds.) |
| 48% | MARIOLOPEZ | 10 | 16-Across and 34-Across star who turned 50 on October 10, 2023 (2 wds.) |
| 47% | STEVEBURNS | 10 | 17-Across and 28-Across host/musician who turns 50 on October 9, 2023 (2 wds.) |
| 47% | PATRICKSTEWART | 14 | "X-Men" actor who plays the title role on 50-Across (2 wds.) |
| 45% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who played 43-Across in 31-Across (2 wds.) |
| 45% | RAMONRODRIGUEZ | 14 | "Charlie's Angels" actor who plays the title GBI special agent on 50-Across (2 wds.) |
| 44% | STEFFIGRAF | 10 | Hall of Fame tennis great who turned 50 on June 14, 2019 (2 wds.) |
| 44% | RANDALLPARK | 11 | Actor who plays Louis, the dad on "Fresh Off the Boat": 2 wds. |
| 44% | DANNYBONADUCE | 13 | Actor who played the wisecracking middle child on "The Partridge Family": 2 wds. |
| 44% | SETHGREEN | 9 | Actor who played Daniel "Oz" Osbourne on "Buffy the Vampire Slayer": 2 wds. |
| 44% | FRANKIEMUNIZ | 12 | Actor who played child prodigy Malcolm on "Malcolm in the Middle": 2 wds. |
| 44% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 44% | SEANGIAMBRONE | 13 | Actor who plays the geeky boy, Adam, on 18-Across: 2 wds. |
| 44% | VICTAYBACK | 10 | Actor who played diner owner Mel on the sitcom "Alice": 2 wds. |
| 43% | MELGIBSON | 9 | "Lethal Weapon" and "Braveheart" actor who turned down the lead role in "Gladiator": 2 wds. |
| 43% | WALTONGOGGINS | 13 | "Justified" actor who plays the main character Wade on 18-Across: 2 wds. |
| 43% | BOBODENKIRK | 11 | "Breaking Bad" actor who plays the lead role on 33-Across: 2 wds. |
| 43% | KENNETHBRANAGH | 14 | "Tenet" actor who plays Hercule Poirot in "Death on the Nile": 2 wds. |
| 43% | BOYDHOLBROOK | 12 | "Logan" actor who plays the Corinthian on "The Sandman": 2 wds. |
| 43% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 43% | SEANCOMBS | 9 | Rapper who turned 50 on November 4, 2019 (2 wds.) |
| 43% | ZACEFRON | 8 | Actor who plays a protégé of 15-Across in "The Greatest Showman": 2 wds. |
| 43% | JAYHERNANDEZ | 12 | "Scandal" actor who plays Magnum on the 2018 reboot of "Magnum, P.I." (2 wds.) |