| 100% | 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. |
| 40% | TROPICTHUNDER | 13 | 2008 movie with Frat Packers Jack Black and Ben Stiller that's set in a jungle: 2 wds. |
| 33% | BEN | 3 | With 70-Across, member of Hollywood's Frat Pack |
| 31% | TROPICTHUNDER | 13 | Action comedy film starring Ben Stiller, Robert Downey Jr. and Jack Black: 2 wds. |
| 30% | ZOOLANDER | 9 | 2001 movie with Frat Packers Ben Stiller, Owen Wilson, Vince Vaughn, and Will Ferrell that's set in the modeling world |
| 30% | OLDSCHOOL | 9 | 2003 movie with Frat Packers Luke Wilson, Vince Vaughn, and Will Ferrell that's actually set at a fraternity: 2 wds. |
| 28% | CARMENELECTRA | 13 | Winner (with Owen Wilson and Amy Smart) of MTV's 2004 Best Kiss Award for "Starsky & Hutch": 2 wds. |
| 26% | WORLDSERIES | 11 | Championship that 17-Across won twice, with the A's and Yankees: 2 wds. |
| 26% | BRUCEALMIGHTY | 13 | 2003 comedy with Jennifer Aniston and Steve Carell: 2 wds. |
| 26% | GRETAGERWIG | 11 | Director of 2017's "Lady Bird" and 17-Across: 2 wds. |
| 25% | KENNYROGERS | 11 | Country Music Hall of Fame singer who collaborated with 17-Across and 28-Across (2 wds.) |
| 25% | MOSTWANTED | 10 | Tupac Shakur's "2 of Amerikaz ___" written along with Snoop Dogg and Daz Dillinger and later was included in his "Greatest Hits" album: 2 wds. |
| 24% | GEORGEORWELL | 12 | British author of "1984" and 17-Across: 2 wds. |
| 24% | KATEMORTON | 10 | Australian author of 17- and 26-Across: 2 wds. |
| 24% | BAZLUHRMANN | 11 | Australian director of 19- and 33-Across who's known for films with pop music soundtracks: 2 wds. |
| 24% | LOVEYOURSELF | 12 | Justin Bieber's acoustic pop song written by him along with Ed Sheeran and Benny Blanco which was the seventh best-selling song of 2016: 2 wds. |
| 24% | DIRESTRAITS | 11 | Music group with siblings as members with hit songs like "Sultans of Swing" and "Money for Nothing": 2 wds. |
| 24% | WHATMAKES | 9 | With 17- and 49-Across, 2011 debut single for One Direction: 2 wds. |
| 24% | SPICEGIRLS | 10 | "Wannabe" band whose members included 17- and 31-Across: 2 wds. |
| 24% | KEVINCOSTNER | 12 | Director and star of 1990's "Dances With Wolves": 2 wds. |
| 23% | TINKERTAILOR | 12 | "___ Soldier, Spy," a 2011 spy film starring Tom Hardy along with the likes of Benedict Cumberbatch and Colin Firth: 2 wds. |
| 23% | THEINTERNSHIP | 13 | Comedy set at Google that stars 39-Across and Owen Wilson: 2 wds. |
| 23% | ABOUTMARY | 9 | "There's Something ___," 1998 comedy starring Cameron Diaz and Ben Stiller: 2 wds. |
| 23% | CAFESOCIETY | 11 | 2016 romantic-comedy starring Jesse Eisenberg (birthday today) and Steve Carell, about a man who falls in love, in Hollywood: 2 wds. |
| 23% | KATEHUDSON | 10 | She and Goldie Hawn are one of Hollywood's best-known mother-daughter duos: 2 wds. |
| 23% | JONSTEWART | 10 | Host of "The Daily Show" between 28- and 17-Across (1999-2015): 2 wds. |
| 23% | HAILEYBALDWIN | 13 | Model from a Hollywood acting family who cohosts 17-Across with Method Man: 2 wds. |
| 23% | PIERCEARROW | 11 | Third member of the Three “P”s of luxury automobiles, along with Packard and Peerless |
| 23% | REDSOX | 6 | Boston ___, MLB team and member of the AL East division that is one of the teams with the most World Series titles: 2 wds. |
| 22% | MIKEBRYAN | 9 | American tennis player who along with Jack Sock won the Men's Doubles in the 2018 Wimbledon Championships: 2 wds. |