| 100% | TROPICTHUNDER | 13 | 2008 movie with Frat Packers Jack Black and Ben Stiller that's set in a jungle: 2 wds. |
| 50% | OLDSCHOOL | 9 | 2003 movie with Frat Packers Luke Wilson, Vince Vaughn, and Will Ferrell that's actually set at a fraternity: 2 wds. |
| 46% | ZOOLANDER | 9 | 2001 movie with Frat Packers Ben Stiller, Owen Wilson, Vince Vaughn, and Will Ferrell that's set in the modeling world |
| 36% | TROPICTHUNDER | 13 | 2008 comedy starring Jack Black as an actor forced to survive in a jungle: 2 wds. |
| 32% | TROPICTHUNDER | 13 | Action comedy film starring Ben Stiller, Robert Downey Jr. and Jack Black: 2 wds. |
| 32% | SCHITTSCREEK | 12 | Sitcom set in Canada with a 2020 same-sex wedding between David and Patrick: 2 wds. |
| 32% | VINCEVAUGHN | 11 | Member of Hollywood's "Frat Pack," along with 17-Across, Ben Stiller, Steve Carell, Jack Black, and Owen and Luke Wilson: 2 wds. |
| 32% | GREYSANATOMY | 12 | Medical drama set in Seattle with a 2011 same-sex wedding between Callie and Arizona: 2 wds. |
| 31% | ORANGEIS | 8 | With 33- and 52-Across, television series set in a women's prison: 2 wds. |
| 30% | NACHOLIBRE | 10 | Jack Black comedy about a cook with a secret life as a wrestler in Mexico (2 wds.) |
| 29% | MYSTICRIVER | 11 | 2003 movie set in Boston, for which Sean Penn and Tim Robbins each won a 1-Across: 2 wds. |
| 29% | NURSEJACKIE | 11 | Showtime comedy-drama set in a hospital that ended this summer: 2 wds. |
| 29% | DRNO | 4 | Villain with the title role in a 1962 movie that introduced 007: 2 wds. |
| 28% | ALLTHAT | 7 | "She's ___," 1999 rom-com set in a high school featuring Freddie Prinze Jr. and Rachael Cook: 2 wds. |
| 28% | TROPICTHUNDER | 13 | 2008 movie about a group of actors who fight in a real-life war: 2 wds. |
| 27% | TROPICTHUNDER | 13 | 2008 action-comedy starring Ben Stiller, about a group of actors shooting for a war film in a jungle: 2 wds. |
| 27% | BLADERUNNER | 11 | 1982 science fiction film set in a dystopian future Los Angeles and about synthetic humans known as replicants: 2 wds. |
| 27% | TROPICTHUNDER | 13 | A comedy starring Ben Stiller and Robert Downey Jr., in which Tom Cruise made a cameo: 2 wds. |
| 27% | MARGARETKEANE | 13 | American painter, featured in a 2014 biopic, known for her women and children with big eyes: 2 wds. |
| 26% | STRANGERTHINGS | 14 | Netflix series set in the 1980s in which single mom Joyce Byers contends with a supernatural monster: 2 wds. |
| 26% | ROLLINGSTONE | 12 | Biweekly pop culture magazine that has been in publication since 1967 and shares its name with a legendary rock band: 2 wds. |
| 26% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 26% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 26% | NIGHTWATCH | 10 | Jayne Anne Phillips novel set in a post-Civil War asylum that's on the longlist for the 2023 National Book Award for Fiction (2 wds.) |
| 25% | THEMASTER | 9 | 2012 movie with Amy Adams as a cult leader's wife: 2 wds. |
| 25% | DEMOLITIONMAN | 13 | 1993 sci-fi film featuring Jack Black which is about an evil crime lord and a risk taking police officer: 2 wds. |
| 25% | HAWAIIFIVEO | 11 | Police drama set in the Aloha State that featured Carol Burnett in a recurring role as Steve McGarrett's aunt (2 wds.) |
| 25% | ONICE | 5 | Like unopened champagne that's waiting in a bucket: 2 wds. |
| 25% | FAMILYMATTERS | 13 | Sitcom set in Chicago that was a spin-off of "Perfect Strangers" (2 wds.) |
| 25% | TRAININGDAY | 11 | 2017 TV series that's based on a Denzel Washington movie and stars Bill Paxton as a cop: 2 wds. |