| 100% | MATTDAMON | 9 | "The Martian" actor who dropped out of Harvard: 2 wds. |
| 73% | MARKZUCKERBERG | 14 | Facebook cofounder who dropped out of Harvard: 2 wds. |
| 72% | OGDENNASH | 9 | "Candy is dandy" poet who dropped out of Harvard: 2 wds. |
| 71% | TRACYMORGAN | 11 | "The Last O.G." actor who dropped out of high school: 2 wds. |
| 61% | DICKSARGENT | 11 | "Bewitched" actor who came out of the closet in 1991 at age 61: 2 wds. |
| 60% | TRAVISKALANICK | 14 | Co-founder of Uber who dropped out of the UCLA: 2 wds. |
| 60% | GEORGETAKEI | 11 | "Star Trek" actor who came out of the closet in 2005 at age 68: 2 wds. |
| 59% | EVANWILLIAMS | 12 | Co-founder of Twitter who dropped out of the University of Nebraska-Lincoln: 2 wds. |
| 58% | DREWBARRYMORE | 13 | "Charlie's Angels" actress who dropped out of high school: 2 wds. |
| 58% | HILARYSWANK | 11 | "Million Dollar Baby" actress who dropped out of high school: 2 wds. |
| 58% | LARRYELLISON | 12 | Co-founder of Oracle Corporation who dropped out of the University of Illinois: 2 wds. |
| 58% | MATTDAMON | 9 | "The Martian" actor who has played in the World Series of Poker (2 wds.) |
| 54% | ORLANDOBLOOM | 12 | Actor who portrayed Legolas in "The Lord of the Rings": 2 wds. |
| 54% | RICHARDGERE | 11 | Actor who accepted the role of Edward in 17-Across: 2 wds. |
| 54% | BENEDICTWONG | 12 | "The Martian" actor who plays a master of the mystical arts in "Doctor Strange in the Multiverse of Madness" (2 wds.) |
| 54% | HARRISONFORD | 12 | Actor who starred in the 1993 movie version of "The Fugitive": 2 wds. |
| 54% | DAVIDJANSSEN | 12 | Actor who starred in the 1960s TV version of "The Fugitive": 2 wds. |
| 54% | ELIJAHWOOD | 10 | Actor who portrayed Frodo Baggins in "The Lord of the Rings": 2 wds. |
| 53% | SAMROCKWELL | 11 | Actor who plays the father in the 2015 remake of 18-Across: 2 wds. |
| 53% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 53% | CRAIGROBINSON | 13 | "The Office" actor who's the host of "The Masked Dancer": 2 wds. |
| 53% | BRUCEWILLIS | 11 | American actor who was in the music video of Gorillaz "Stylo": 2 wds. |
| 52% | JOSEPHCOTTEN | 12 | Actor who played a reporter and friend of the title character in 17-Across: 2 wds. |
| 52% | RONALDREAGAN | 12 | American actor who served as the 40th President of the United States: 2 wds. |
| 52% | CARLWEATHERS | 12 | "Rocky" actor who played briefly for the Oakland Raiders of the NFL: 2 wds. |
| 52% | CHANNINGTATUM | 13 | Actor who plays one of the studio's stars in 18-Across: 2 wds. |
| 52% | KIRKDOUGLAS | 11 | "Spartacus" actor who received the French Legion of Honor medal in 1985: 2 wds. |
| 52% | JOSEPHQUINN | 11 | "Stranger Things" actor who stars in the 2024 prequel of 13-Across: 2 wds. |
| 52% | ROBERTDUVALL | 12 | Actor who says "I love the smell of napalm in the morning" in 31-Across: 2 wds |
| 52% | CARLOSVALDES | 12 | Actor who plays Cisco Ramon on "The Flash" which is a part of the Arrowverse: 2 wds. |