| 100% | WAITING | 7 | 2005 comedy film starring Ryan Reynolds, Anna Faris, and Justin Long, set in a restaurant called Shenaniganz |
| 31% | DEADPOOL | 8 | 2016 action-comedy film starring Ryan Reynolds in the title role |
| 31% | YARD | 4 | "The Longest ___,' a 2005 sports comedy film starring Adam Sandler and Chris Rock |
| 29% | VANWILDER | 9 | Ryan Reynolds campus comedy film that featured cameos by NBA stars Darius Miles, Quentin Richardson, and Lamar Odom (2 wds.) |
| 29% | FRIENDSWITH | 11 | "___ Benefits," 2011 romantic comedy film that starred Justin Timberlake and Mila Kunis in the lead roles: 2 wds. |
| 28% | GREENLANTERN | 12 | 2011 action film starring Ryan Reynolds in the title role |
| 28% | HUNDRED | 7 | "The ___-Foot Journey," 2014 film starring Helen Mirren and Om Puri about two competing restaurants in a French village |
| 28% | DEATHONTHENILE | 14 | Novel by 19-Across set in Egypt adapted into a 2022 film starring and directed by 33-Across (4 wds.) |
| 27% | ROADTOUTOPIA | 12 | Alaska-set 1945 film comedy in a series starring Bing Crosby, Bob Hope and Dorothy Lamour |
| 27% | ROAD | 4 | & 17A 1947 film in a comedy series starring Bing Crosby and Bob Hope |
| 27% | SEATTLE | 7 | "Sleepless in ___," 1993 romantic comedy film starring Tom Hanks and Meg Ryan |
| 27% | ROUGHNIGHT | 10 | A 2017 dark comedy film in which Scarlett Johansson stars alongside Zoe Kravitz and Kate McKinnon: 2 wds. |
| 27% | LOGANLUCKY | 10 | A 2017 heist comedy film in which Seth MacFarlane stars alongside Channing Tatum and Daniel Craig: 2 wds. |
| 27% | TOUGHGUYS | 9 | A 1986 action comedy film in which Kirk Douglas starred alongside Eli Wallach and Dana Carvey: 2 wds. |
| 27% | PIKACHU | 7 | Detective in a 2019 Ryan Reynolds film |
| 26% | THEMATADOR | 10 | 2005 comedy-drama film starring Pierce Brosnan and Greg Kinnear |
| 26% | GUARD | 5 | "The ___," 2011 crime comedy film starring Don Cheadle that's set in Ireland |
| 26% | BRING | 5 | "___ It On," 2000 sports comedy film starring Kirsten Dunst in a leading role |
| 26% | THERE | 5 | "Are We ___ Yet?" 2005 comedy film starring Ice Cube, about a road trip on New Year's Eve |
| 26% | GOTMAIL | 7 | "You've ___," 1998 romantic comedy film starring Tom Hanks and Meg Ryan: 2 wds. |
| 26% | BUTCHER | 7 | "The ___ Boy," 1997 black comedy film starring Fiona Shaw that's set in Ireland |
| 26% | GOONIES | 7 | "The ___," 1985 adventure comedy film starring Sean Astin, Josh Brolin, and an ensemble cast as a group of kids living in the "Goon Docks" |
| 25% | MATADOR | 7 | The —, 2005 comedy-drama film starring Pierce Brosnan and Greg Kinnear |
| 25% | MATADOR | 7 | The -, 2005 comedy-drama film starring Pierce Brosnan and Greg Kinnear |
| 25% | GREENLANTERN | 12 | Superhero played by Ryan Reynolds in a 2011 film (2 wds.) |
| 25% | PIKACHU | 7 | Yellow "detective" voiced by Ryan Reynolds in a 2019 Pokémon film |
| 25% | BEWITCHED | 9 | 2005 film comedy starring Nicole Kidman and Will Ferrell |