| 100% | BROTHER | 7 | O __, Where Art Thou? crime comedy with Clooney |
| 56% | BROTHER | 7 | "O ___, Where Art Thou?" (2000 George Clooney film) |
| 43% | HOMEALONE | 9 | "O Brother, Where Art Thou?" [1990] |
| 42% | PAINHUSTLERS | 12 | 2023 Netflix crime comedy with Catherine O'Hara as the mother of a woman marketing opioids: 2 wds. |
| 40% | THOU | 4 | "O Brother, Where Art ___?," George Clooney film |
| 40% | THOU | 4 | "O Brother, Where Art ___?" (George Clooney film) |
| 39% | ABBEYS | 6 | Oh, brothers, where art thou? |
| 38% | KLAN | 4 | Kind of meeting in "O Brother, Where Art Thou?" |
| 36% | COEN | 4 | Either brother who co-wrote "O Brother, Where Art Thou?" |
| 34% | AMA | 3 | "I ___ Man of Constant Sorrow" ("O Brother, Where Art Thou?" song): 2 wds. |
| 34% | ART | 3 | "O Brother, Where ___ Thou?," 2000 film starring George Clooney that featured musicians like John Hartford |
| 34% | AMA | 3 | “I ___ Man of Constant Sorrow” (song in “O Brother, Where Art Thou?”) |
| 34% | COEN | 4 | Last name of the brothers who directed "O Brother, Where Art Thou?" |
| 34% | ART | 3 | "O Brother, Where ___ Thou?" 2000 comedy film loosely based on "The Odyssey" |
| 32% | AMA | 3 | "I ___ Man of Constant Sorrow" (song in "O Brother, Where Art Thou?"): 2 wds. |
| 32% | HOLLYHUNTER | 11 | "The Piano" actress who played Penny in "O Brother, Where Art Thou?": 2 wds. |
| 32% | THOU | 4 | "O Brother, Where Art ___?" 2000 movie featuring George Clooney loosely based on Homer's epic "The Odyssey" |
| 32% | TBONE | 5 | Burnett who won four Grammys for the "O Brother, Where Art Thou?" soundtrack: 2 wds. |
| 31% | GEORGECLOONEY | 13 | "Ocean's Eleven" actor who played Everett in "O Brother, Where Art Thou?": 2 wds. |
| 31% | JOHNGOODMAN | 11 | "The Conners" actor who played Big Dan in "O Brother, Where Art Thou?": 2 wds. |
| 31% | GIRLS | 5 | "Good ___," crime comedy series starring Mae Whitman, with a "good" title but many criminals |
| 31% | SCTV | 4 | Sketch comedy series with Eugene Levy and Catherine O'Hara |
| 30% | THOU | 4 | "O Brother, Where Art ___" |
| 30% | THOU | 4 | "O Brother, Where Art ___?" |
| 30% | FROMDUSK | 8 | With 31-Across, 1996 comedy crime film directed by Robert Rodriguez: 2 wds. |
| 30% | SCTV | 4 | Sketch comedy series with Eugene Levy and Catherine O’Hara |
| 30% | THOU | 4 | O Brother, Where Art ___? (fictional movie in Sullivan's Travels) |
| 29% | ART | 3 | "O Brother, Where ___ Thou?" |
| 29% | GOODBYE | 7 | With 35-Across, 1969 film where Peter O'Toole played a stodgy Latin teacher |
| 29% | HOWTOSTEAL | 10 | & 1D 1966 comedy crime film starring Peter O'Toole and Audrey Hepburn |