| 100% | SIB | 3 | Owen Wilson and Luke Wilson are ___lings |
| 57% | OLDSCHOOL | 9 | 2003 film comedy starring Luke Wilson and Will Ferrell |
| 50% | 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. |
| 50% | ZOOLANDER | 9 | 2001 movie with Frat Packers Ben Stiller, Owen Wilson, Vince Vaughn, and Will Ferrell that's set in the modeling world |
| 48% | OLDSCHOOL | 9 | 2003 movie with Frat Packers Luke Wilson, Vince Vaughn, and Will Ferrell that's actually set at a fraternity: 2 wds. |
| 47% | HALLPASS | 8 | 2011 film comedy starring Owen Wilson and Jason Sudeikis |
| 47% | NOESCAPE | 8 | 2015 action film starring Owen Wilson and Lake Bell |
| 47% | MIDNIGHTINPARIS | 15 | 2011 film co-starring Owen Wilson and Rachel McAdams |
| 47% | VACANCY | 7 | 2007 horror film starring Kate Beckinsale and Luke Wilson |
| 47% | UNCLE | 5 | Luke Wilson, to Owen Wilson's children |
| 45% | ACTORS | 6 | People like Clive Owen and Owen Wilson |
| 44% | MYDOG | 5 | & 6D 2000 family film starring Frankie Muniz, Diane Lane and Luke Wilson |
| 44% | DUPREE | 6 | "You, Me and ___" (2006 Owen Wilson rom-com) |
| 44% | DUPREE | 6 | "You, Me and __": rom-com starring Owen Wilson |
| 43% | CARS | 4 | 2006 animated film featuring the voice talent of Owen Wilson and Paul Newman |
| 43% | THIRDWHEEL | 10 | The —, 2002 romcom starring Luke Wilson and Denise Richards |
| 42% | NOON | 4 | Jackie Chan and Owen Wilson starrer western comedy film "Shanghai ___" |
| 42% | LOKI | 4 | 2021 Marvel TV series starring Tom Hiddleston and Owen Wilson |
| 42% | INTERNSHIP | 10 | The —, 2013 film comedy starring Vince Vaughn and Owen Wilson |
| 42% | ISPY | 4 | 2003 action-comedy film starring Eddie Murphy and Owen Wilson |
| 42% | ISPY | 4 | 2002 Betty Thomas comedy film starring Eddie Murphy and Owen Wilson |
| 42% | ARE | 3 | "___ You Here," 2013 comedy drama starring Amy Poehler and Owen Wilson |
| 41% | DAD | 3 | What Phil is to Haley, Alex, and Luke on "Modern Family" |
| 41% | BROTHER | 7 | Luke and Leia are __ and sister in Star Wars |
| 40% | WES | 3 | Frequent director of Owen, Luke, Bill, and Tilda |
| 40% | ROSS | 4 | Bob on whom Owen Wilson's character is based in 2023's "Paint" |
| 40% | THEINTERNSHIP | 13 | Comedy set at Google that stars 39-Across and Owen Wilson: 2 wds. |