| 100% | GHOSTWORLD | 10 | 2001 black comedy in which Steve Buscemi plays a lonely man named Seymour: 2 wds. |
| 47% | RESERVOIRDOGS | 13 | 1992 heist film in which Steve Buscemi plays a criminal nicknamed Mr. Pink: 2 wds. |
| 44% | LEGALLYBLONDE | 13 | 2001 comedy in which Reese Witherspoon played a sorority girl who excels at Harvard Law School: 2 wds. |
| 41% | THEMEXICAN | 10 | 2001 Brad Pitt/Julia Roberts adventure comedy in which Gene Hackman plays a mobster: 2 wds. |
| 38% | THEBIRDCAGE | 11 | 1996 film comedy in which Dianne Wiest played a conservative senator's wife: 2 wds. |
| 38% | TOOTHFAIRY | 10 | A 2010 comedy film starring Dwayne Johnson in which Seth MacFarlane played a character named Ziggy: 2 wds. |
| 38% | LEGALLYBLONDE | 13 | 2001 comedy in which 18-Across plays bubbly law student Elle Woods: 2 wds. |
| 37% | BLACKSWAN | 9 | 2010 drama in which Mila Kunis played a dancer named Lily: 2 wds. |
| 36% | THEFUGITIVE | 11 | Harrison Ford's 1993 movie (25th anniversary) in which he plays a man who is wrongfully convicted: 2 wds. |
| 35% | LOVEACTUALLY | 12 | 2003 rom-com in which Alan Rickman played a married man flirting with his secretary: 2 wds. |
| 35% | SPOTLESSMIND | 12 | "Eternal Sunshine of the ___," cult movie in which Jim Carrey (birthday today) plays a man who undergoes a memory-erasing procedure: 2 wds. |
| 34% | THEOFFICE | 9 | A comedy which starred Steve Carell as Michael Scott, in which 17-Across played his rival, Charles Miner: 2 wds. |
| 34% | GALAXYQUEST | 11 | 1999 sci-fi comedy in which Alan Rickman played an actor from a cult TV show: 2 wds. |
| 33% | DONTLOOKUP | 10 | 2021 black comedy in which Leonardo DiCaprio plays an astronomy professor: 3 wds. |
| 33% | MOULINROUGE | 11 | Movie in which Nicole Kidman played a prostitute: 2 wds. |
| 33% | PRETTYWOMAN | 11 | Movie in which Julia Roberts played a prostitute: 2 wds. |
| 33% | OHGOD | 5 | 1977 comedy in which George Burns plays the Lord: 2 wds. |
| 33% | TRADINGPLACES | 13 | Movie in which Jamie Lee Curtis played a prostitute: 2 wds. |
| 33% | ECHOBURNING | 11 | 2001 novel by Lee Child in which Jack Reacher helps a woman named Carmen: 2 wds. |
| 33% | ROCKOFAGES | 10 | A musical comedy-drama in which Tom Cruise plays a self-indulgent rock star who plays for a band named "Arsenal": 3 wds |
| 32% | BILLYMADISON | 12 | 1995 classroom comedy in which 29-Across played the title role: 2 wds. |
| 32% | HAPPYGILMORE | 12 | 1996 sports comedy in which 29-Across played the title role: 2 wds. |
| 32% | BRUCEALMIGHTY | 13 | 2003 movie in which 15-Across played a deity: 2 wds. |
| 32% | KATHYBATES | 10 | Actress who plays a marijuana dispensary owner in the new Netflix comedy "Disjointed": 2 wds. |
| 32% | ELLAENCHANTED | 13 | 52-Across plays a giantess in this 2004 romantic comedy starring Anne Hathaway: 2 wds. |
| 32% | CLARASHEART | 11 | 1988 film in which Whoopi Goldberg plays a nanny: 2 wds. |
| 32% | INTREATMENT | 11 | HBO drama in which Dianne Wiest played a psychotherapist: 2 wds. |
| 32% | PRINCESSBRIDE | 13 | With "The," 1987 comedy in which 15-Across played swordsman Inigo Montoya: 2 wds |
| 32% | MISTERROBERTS | 13 | 1955 naval comedy in which Jack Lemmon played Ensign Pulver: 2 wds. |
| 32% | WORKINGGIRL | 11 | 1988 film in which Sigourney Weaver plays a scheming executive: 2 wds. |