| 100% | DREWBARRYMORE | 13 | Adam Sandler's costar in "Blended" and "50 First Dates": 2 wds. |
| 49% | TEALEONI | 8 | Adam Sandler's "Spanglish" costar: 2 wds. |
| 46% | DREW | 4 | ___ Barrymore and Adam Sandler, "50 First Dates" actors who have starred in multiple rom-coms together |
| 45% | JUDYGARLAND | 11 | Mickey Rooney's costar in 18-Across and many other movies: 2 wds. |
| 45% | WALTERMATTHAU | 13 | Jack Lemmon's costar in 18- and 37-Across: 2 wds. |
| 45% | JENNIFERLOPEZ | 13 | Ben Affleck's costar in "Gigli" and "Jersey Girl": 2 wds. |
| 43% | BARRYMORE | 9 | She starred in 50 First Dates and Charlie's Angels |
| 43% | HARRISONFORD | 12 | Ke Huy Quan's costar in 1984's "Indiana Jones and the Temple of Doom": 2 wds. |
| 42% | JUSTINTHEROUX | 13 | Jennifer Aniston's costar in "Wanderlust"—and now her husband: 2 wds. |
| 41% | MARKHAMILL | 10 | Carrie Fisher's costar in "Star Wars" and "The Last Jedi" who said "I learned so much from her": 2 wds. |
| 41% | CHANNINGTATUM | 13 | Jenna Dewan's costar in "Step Up"—and now her husband: 2 wds. |
| 40% | DREWBARRYMORE | 13 | "50 First Dates" actress who's launching a beauty magazine called Flower Press: 2 wds. |
| 40% | SANDRABULLOCK | 13 | Keanu Reeves' costar in "Speed" and "The Lake House": 2 wds. |
| 40% | SANDLER | 7 | Adam, star of 50 First Dates and The Waterboy |
| 40% | DREWBARRYMORE | 13 | "50 First Dates" actress who played a private investigator named Dylan in "Charlie's Angels": 2 wds. |
| 39% | SETHROGEN | 9 | James Franco's costar in "The Interview": 2 wds. |
| 38% | SEANASTIN | 9 | Ke Huy Quan's costar in 1985's "The Goonies": 2 wds. |
| 37% | RYANREYNOLDS | 12 | Jason Bateman's costar in the 2011 movie "The Change-Up": 2 wds. |
| 37% | JOHNTRAVOLTA | 12 | Rene Russo's costar in the 1995 gangster comedy "Get Shorty": 2 wds. |
| 37% | KEVINCOSTNER | 12 | Rene Russo's costar in the 1996 romantic comedy "Tin Cup": 2 wds. |
| 37% | HAPPYGILMORE | 12 | 1996 golf film starring Adam Sandler and Julie Bowen: 2 wds. |
| 37% | UNCUTGEMS | 9 | 2019 crime thriller starring Adam Sandler and Idina Menzel: 2 wds. |
| 36% | JACKBLACK | 9 | Ke Huy Quan's costar in 2024's "Kung Fu Panda 4": 2 wds. |
| 36% | JASONBATEMAN | 12 | Jennifer Aniston's costar in the 2010 romantic comedy/drama "The Switch": 2 wds. |
| 36% | PUNCHDRUNKLOVE | 14 | 2002 romantic drama starring Adam Sandler and Emily Watson: 2 wds., hyph. |
| 36% | SETHROGEN | 9 | James Franco's costar in 31-Across: 2 wds. |
| 36% | MICHELLEYEOH | 12 | Ke Huy Quan's costar in 2022's "Everything Everywhere All at Once": 2 wds. |
| 36% | ADAMSANDLER | 11 | Jennifer Aniston's costar in the 2011 romantic comedy "Just Go With It": 2 wds. |
| 36% | VINCEVAUGHN | 11 | Jennifer Aniston's costar in the 2006 romantic comedy/drama "The Break-Up": 2 wds. |
| 36% | GINGERROGERS | 12 | Fred Astaire's costar in "Top Hat," who was born Virginia Katherine McMath: 2 wds. |