| 100% | TEVYE | 5 | Fiddler on the Roof character who sings "If I Were a Rich Man" |
| 53% | IFI | 3 | "___ Were a Rich Man" (song from "Fiddler on the Roof") |
| 53% | IFI | 3 | "___ Were a Rich Man" ("Fiddler on the Roof" song): 2 wds. |
| 44% | DOROTHY | 7 | Character who sings with the Scarecrow in "If I Only Had a Brain" |
| 44% | ILSA | 4 | Character who says “Kiss me as if it were the last time” to Rick, in a 1942 film |
| 44% | TEVYE | 5 | "If I Were a Rich Man" singer |
| 44% | TEVYE | 5 | ''If I Were a Rich Man'' singer |
| 42% | REB | 3 | Title for Tevye in "If I Were a Rich Man" |
| 42% | ONCELER | 7 | Character who sings "How Bad Can I Be?" in The Lorax |
| 41% | BOBBYDARWIN | 11 | Singer who sang "If I Were a Giant Sea Tortoise"? |
| 41% | RABBI | 5 | Fiddler on the Roof character |
| 40% | ATTIC | 5 | I am a hidden room of mysteries nestled under the roof. Who am I? |
| 40% | ARICH | 5 | “If I Were ___ Man” (“Fiddler on the Roof” tune) |
| 40% | ELMO | 4 | Character who's been a regular on "Sesame Street" since the 1980s |
| 39% | CHALK | 5 | I am a teacher's best friend. I help them write on the blackboard. Who am I? |
| 39% | ARICH | 5 | "If I Were___ Man" (Tevye song in "Fiddler on the Roof") (2 wds.) |
| 39% | SUPERMAN | 8 | Character who is lifting a car on the cover of "Action Comics" #1 |
| 39% | LAHR | 4 | Bert who sang "If I Were King of the Forest" |
| 38% | ELMO | 4 | Furry character who's been a regular on "Sesame Street" since the 1980s |
| 38% | LAHR | 4 | First actor who sang "If I Were King of the Forest" |
| 38% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 37% | MAYAANGELOU | 11 | "I Know Why the Caged Bird Sings" writer who was honored on a U.S. postage stamp in 2015 (2 wds.) |
| 37% | SIMBA | 5 | Disney character who sings the lyric "I'm working on my roar!" |
| 37% | ERMA | 4 | Bombeck who wrote If Life Is a Bowl of Cherries, What Am I Doing in the Pits? |
| 37% | ILSA | 4 | Film character who says "Kiss me as if it were the last time" |
| 36% | SISTER | 6 | With 29-Across, Pam Ferris character who was a midwife and nun in Nonnatus House on "Call the Midwife" |
| 36% | MRDARCY | 7 | To whom it is said, “I had not known you a month before I felt that you were the last man in the world whom I could ever be prevailed on to marry” |
| 36% | NEMO | 4 | Fictional character who says "I am not what you call a civilized man!" |
| 36% | AHAB | 4 | Literary character who cries "Talk not to me of blasphemy, man; I’d strike the sun if it insulted me" |
| 36% | ILSA | 4 | Classic movie character who says "Kiss me as if it were the last time" |