| 100% | DONTLOOKUP | 10 | 2021 black comedy in which Leonardo DiCaprio plays an astronomy professor: 3 wds. |
| 48% | THEGREATGATSBY | 14 | 2013 drama in which Leonardo DiCaprio plays a 1920s millionaire: 3 wds. |
| 40% | THEAVIATOR | 10 | 2004 biographical drama in which Leonardo DiCaprio plays Howard Hughes: 2 wds. |
| 38% | GHOSTWORLD | 10 | 2001 black comedy in which Steve Buscemi plays a lonely man named Seymour: 2 wds. |
| 38% | THEREVENANT | 11 | 2015 Leonardo DiCaprio film in which he plays frontiersman Hugh Glass: 2 wds. |
| 38% | THEDEPARTED | 11 | 2006 Leonardo DiCaprio film in which he plays officer Billy Costigan: 2 wds. |
| 38% | THEODDCOUPLE | 12 | 1968 comedy in which Jack Lemmon played neatnik Felix Ungar: 3 wds. |
| 37% | SHUTTERISLAND | 13 | 2010 Leonardo DiCaprio film in which he plays US Marshal Teddy Daniels: 2 wds. |
| 36% | DONTLOOKUP | 10 | 2021 film in which Jennifer Lawrence plays astronomer Kate Dibiasky: 3 wds. |
| 35% | GILBERTGRAPE | 12 | "What's Eating ___," film for which Leonardo DiCaprio (birthday today) received an Oscar nomination for best actor in a supporting role: 2 wds. |
| 34% | GALAXYQUEST | 11 | 1999 sci-fi comedy in which Alan Rickman played an actor from a cult TV show: 2 wds. |
| 34% | THEBIGYEAR | 10 | Actor Jim Parsons played an avid bird blogger named Ichabod Crane in this 2011 comedy film starring Steve Martin: 3 wds. |
| 34% | WHATWOMENWANT | 13 | 2000 romantic fantasy in which 9-/53-Across played an ad executive: 3 wds. |
| 31% | THORRAGNAROK | 12 | Marvel sequel in which "The Wire" star Idris Elba played Heimdall: 3 wds. |
| 31% | LEGALLYBLONDE | 13 | 2001 comedy in which 18-Across plays bubbly law student Elle Woods: 2 wds. |
| 31% | BILLYMADISON | 12 | 1995 classroom comedy in which 29-Across played the title role: 2 wds. |
| 31% | HAPPYGILMORE | 12 | 1996 sports comedy in which 29-Across played the title role: 2 wds. |
| 31% | PARENTHOOD | 10 | 1989 ensemble family comedy in which Rick Moranis played an obsessive father |
| 31% | STEVEJOBS | 9 | 2015 movie in which Kate Winslet plays an Apple marketing executive: 2 wds. |
| 31% | OHGOD | 5 | 1977 comedy in which George Burns plays the Lord: 2 wds. |
| 30% | THECOLORPURPLE | 14 | 1985 drama in which 1-Across played Sofia: 3 wds. |
| 30% | SEAOFLOVE | 9 | 1989 Al Pacino movie in which he plays homicide detective Frank Keller: 3 wds. |
| 30% | LILYJAMES | 9 | Actress who plays an English archaeologist in the 2021 film "The Dig": 2 wds. |
| 30% | SAMUELLJACKSON | 14 | "Pulp Fiction" actor who plays an assassin in "The Hitman's Bodyguard": 3 wds. |
| 30% | THEREADER | 9 | 2008 movie in which Kate Winslet plays an illiterate woman: 2 wds. |
| 30% | THEHURRICANE | 12 | 1999 film in which Denzel Washington played an imprisoned boxer: 2 wds. |
| 30% | NOVEMBER | 8 | Month in which Leonardo DiCaprio was born |
| 29% | PRINCESSBRIDE | 13 | With "The," 1987 comedy in which 15-Across played swordsman Inigo Montoya: 2 wds |
| 29% | MISTERROBERTS | 13 | 1955 naval comedy in which Jack Lemmon played Ensign Pulver: 2 wds. |
| 29% | INTOTHEWOODS | 12 | Film musical in which James Corden plays a baker: 3 wds. |