| 100% | SORRY | 5 | "Who's ___ Now?": 1923 song |
| 66% | RUER | 4 | Who's sorry now? |
| 62% | ELTON | 5 | John who's now a Sir |
| 59% | DRINKING | 8 | Pepsi slogan: Look who's __ Pepsi now |
| 58% | LIPA | 4 | Song superstar who's Mermaid Barbie (2023) |
| 56% | IDA | 3 | Song girl who's "sweet as apple cider" |
| 55% | AROD | 4 | Former Yank who's now part owner of the Timberwolves |
| 55% | IPANEMA | 7 | Whence a girl who's "like a samba," in song |
| 55% | CRIMINAL | 8 | Person who's broken the law; 1996 Fiona Apple song |
| 55% | IRENE | 5 | Woman who's bid good night in an old song |
| 55% | NERD | 4 | Once uncool sort who's now sort of cool |
| 55% | HASBEEN | 7 | Formerly famous person who's now largely forgotten: Hyph. |
| 55% | AIMEE | 5 | Mann who wrote songs for 1999's "Magnolia" |
| 54% | ORA | 3 | Rita who's featured on the Iggy Azalea song "Black Widow" |
| 54% | HURRICANECARTER | 15 | Wrongfully imprisoned boxer who's the subject of a Dylan song |
| 54% | IDA | 3 | Girl who's "sweet as apple cider," per an old song |
| 54% | ELWAY | 5 | Former quarterback John who's now manager of the Broncos |
| 54% | DEREKJETER | 10 | Ex-Yankee who's now CEO of the Marlins |
| 53% | CONNIE | 6 | Francis who sang "Who's Sorry Now?" |
| 53% | JOHN | 4 | Denver who sang "Annie's Song" |
| 52% | ROMO | 4 | Retired quarterback Tony who's now an NFL analyst for CBS |
| 52% | HERE | 4 | Giorgio Moroder's song, featuring Kylie Minogue, "Right ___, Right Now" |
| 52% | SIA | 3 | One-named singer who wrote Rihanna's hit song "Diamonds" |
| 52% | FROGGY | 6 | One who "went a-courtin'," in a children's song |
| 52% | LAYLA | 5 | Song title character who's "got me on my knees" |
| 52% | OHOLEYKNIGHT | 12 | Song about a guy who's a lousy jouster? |
| 52% | LIN | 3 | Jeremy ___ (Knicks phenom who's now a Rocket) |
| 52% | CANIGO | 6 | "___ Now" (Jennifer Love Hewitt song) |
| 52% | ITS | 3 | "__ Now or Never"; Elvis song |
| 51% | CONNIEFRANCIS | 13 | “Who’s Sorry Now?” singer |