| 100% | AMA | 3 | "I ___ Man of Constant Sorrow" (song in "O Brother, Where Art Thou?"): 2 wds. |
| 85% | AMA | 3 | "I ___ Man of Constant Sorrow" ("O Brother, Where Art Thou?" song): 2 wds. |
| 84% | AMA | 3 | “I ___ Man of Constant Sorrow” (song in “O Brother, Where Art Thou?”) |
| 53% | AMA | 3 | "I ___ Man of Constant Sorrow" (Soggy Bottom Boys song) (2 wds.) |
| 53% | HOLLYHUNTER | 11 | "The Piano" actress who played Penny in "O Brother, Where Art Thou?": 2 wds. |
| 51% | GEORGECLOONEY | 13 | "Ocean's Eleven" actor who played Everett in "O Brother, Where Art Thou?": 2 wds. |
| 51% | JOHNGOODMAN | 11 | "The Conners" actor who played Big Dan in "O Brother, Where Art Thou?": 2 wds. |
| 45% | KLAN | 4 | Kind of meeting in "O Brother, Where Art Thou?" |
| 44% | AMA | 3 | "I __ Man of Constant Sorrow"; folk song |
| 42% | TBONE | 5 | Burnett who won four Grammys for the "O Brother, Where Art Thou?" soundtrack: 2 wds. |
| 38% | AMA | 3 | "I __ Man of Constant Sorrow" |
| 38% | AMA | 3 | "I ___ Man of Constant Sorrow" |
| 38% | THOU | 4 | O Brother, Where Art ___? (fictional movie in Sullivan's Travels) |
| 35% | HOMEALONE | 9 | "O Brother, Where Art Thou?" [1990] |
| 34% | IAMA | 4 | "_ __ _ Man of Constant Sorrow" |
| 33% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 33% | IFI | 3 | "___ Only Had a Brain" (the Scarecrow's song in "The Wizard of Oz"): 2 wds. |
| 33% | COEN | 4 | Last name of the brothers who directed "O Brother, Where Art Thou?" |
| 32% | THEMALL | 7 | "Let's Go to ___," Robin Sparkles' hit song in "How I Met Your Mother": 2 wds. |
| 32% | LETITBE | 7 | Beatles song that begins "When I find myself in times of trouble" (3 wds.) |
| 32% | LETITBE | 7 | Beatles song that begins, "When I find myself in times of trouble" (3 wds.) |
| 31% | HOUNDDOG | 8 | Elvis Presley hit song in the Grammy Hall of Fame (2 wds.) |
| 30% | ABBEYS | 6 | Oh, brothers, where art thou? |
| 30% | ARICH | 5 | "If I Were___ Man" (Tevye song in "Fiddler on the Roof") (2 wds.) |
| 30% | IMA | 3 | "___ man of my word": 2 wds. |
| 30% | TIMEAFTERTIME | 13 | 1984 song that opens, "Lying in my bed I hear the clock tick, / And think of you" (3 wds.) |
| 29% | MRKITE | 6 | Subject of a benefit, in a Beatles song: 2 wds. |
| 28% | BROTHER | 7 | O __, Where Art Thou? crime comedy with Clooney |
| 28% | HAPPY | 5 | 2013 song by Pharrell Williams that is on the soundtrack of "Despicable Me 2" and was Billboard's number-one single in 2014 |
| 28% | STEVIEWONDER | 12 | Singer with four #1 songs in the 1980s, including "I Just Called to Say I Love You" (2 wds.) |