| 100% | SEANCOMBS | 9 | Rapper who turned 50 on November 4, 2019 (2 wds.) |
| 74% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 65% | KENGRIFFEYJR | 12 | Baseball Hall of Famer who turned 50 on November 21, 2019 (3 wds.) |
| 63% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 58% | STEFFIGRAF | 10 | Hall of Fame tennis great who turned 50 on June 14, 2019 (2 wds.) |
| 56% | DANIELCRAIG | 11 | "Skyfall" actor who turned 50 on March 2, 2018 (2 wds.) |
| 55% | LLCOOLJ | 7 | Actor and rapper who turned 50 on January 14, 2018 (3 wds.) |
| 55% | PATTONOSWALT | 12 | Comedian/actor of 14-Across and 29-Across who turned 50 on January 27, 2019 (2 wds.) |
| 50% | MOLLYRINGWALD | 13 | "Sixteen Candles" actress who turned 50 on February 18, 2018 (2 wds.) |
| 49% | FAITHHILL | 9 | "This Kiss" country singer who turns 50 on September 21, 2017 (2 wds.) |
| 49% | HUGHJACKMAN | 11 | "The Greatest Showman" actor who turns 50 on October 12, 2018 (2 wds.) |
| 48% | ROBERTPATRICK | 13 | "Scorpion" actor who turns 60 on November 5, 2018 (2 wds.) |
| 48% | NICKLACHEY | 10 | TV host and "The Masked Singer" winner who turns 50 years old on November 9, 2023 (2 wds.) |
| 48% | PAULRUDD | 8 | "Ant-Man" and 15-Across, 22-Across, and 37-Across actor who turns 50 on April 6 (2 wds.) |
| 48% | CHRISTIANBALE | 13 | "The Fighter" Oscar winner who turned 50 years old on January 30, 2024 (2 wds.) |
| 48% | JAMIEFOXX | 9 | "Ray" Best Actor Oscar winner who turns 50 on December 13, 2017 (2 wds.) |
| 47% | VINDIESEL | 9 | "The Fate of the Furious" actor who turned 50 on July 18, 2017 (2 wds.) |
| 47% | MARIOLOPEZ | 10 | 16-Across and 34-Across star who turned 50 on October 10, 2023 (2 wds.) |
| 46% | KENDRICKLAMAR | 13 | Grammy-winning rapper who turned 30 on June 17, 2017 (2 wds.) |
| 46% | TIMMCGRAW | 9 | "Just to See You Smile" country singer who turned 50 on May 1, 2017 (2 wds.) |
| 46% | STEVEBURNS | 10 | 17-Across and 28-Across host/musician who turns 50 on October 9, 2023 (2 wds.) |
| 45% | HILARYSWANK | 11 | "Million Dollar Baby," 19-Across, and 34-Across actress who turned 50 years old on July 30, 2024 (2 wds.) |
| 45% | KATEUPTON | 9 | Supermodel who married Houston Astros pitcher Justin Verlander on November 4: 2 wds. |
| 45% | ELIZABETHBANKS | 14 | 16-Across, 34-Across, and "Cocaine Bear" actress and filmmaker who turns 50 years old on February 10, 2024 (2 wds.) |
| 45% | TINAFEY | 7 | Multi-award-winning comic, actor, writer, and producer who turned 50 on May 18, 2020 (2 wds.) |
| 44% | KANYEWEST | 9 | Rapper who performed "Jesus Walks" on the SNL40 anniversary special: 2 wds. |
| 43% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 42% | MARKWAHLBERG | 12 | "Boogie Nights" star who turns 50 in 2021 (2 wds.) |
| 42% | EWANMCGREGOR | 12 | "Star Wars" star who turns 50 in 2021 (2 wds.) |
| 42% | JENNIFERLOPEZ | 13 | Multitalented superstar who turns 50 today (2 wds.) |