| 100% | ELTONJOHN | 9 | "Candle in the Wind" singer/pianist who's the subject of 41-Across: 2 wds. |
| 65% | ELTONJOHN | 9 | "Candle in the Wind" singer who said of his upcoming farewell tour, "It's a way of going out with a bang": 2 wds. |
| 58% | MARILYNMONROE | 13 | Actress who's the subject of 54-Across: 2 wds. |
| 56% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 53% | ADAMLEVINE | 10 | Singer who appears nude in the video of Maroon 5's 2015 single, "This Summer": 2 wds. |
| 53% | JOHNNYCASH | 10 | Country singer who was the subject of the 2005 biopic "Walk the Line": 2 wds. |
| 53% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 53% | RITCHIEVALENS | 13 | Rock singer who was the subject of the 1987 biopic "La Bamba": 2 wds. |
| 53% | DONNYOSMOND | 11 | Singer who dances in front of the Schrödinger equation in "Weird Al" Yankovic's "White & Nerdy" video: 2 wds. |
| 53% | JAMESFRANCO | 11 | "The Interview" star who was the subject of a Comedy Central Roast in 2013: 2 wds. |
| 53% | DONALDTRUMP | 11 | "The Apprentice" host who was the subject of a Comedy Central Roast in 2011: 2 wds. |
| 52% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 52% | EARTHAKITT | 10 | "Santa Baby" singer who was the voice of villainous Yzma in Disney's "The Emperor's New Groove": 2 wds. |
| 52% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 52% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 52% | ROSEANNEBARR | 12 | 1990s sitcom star who was the subject of a Comedy Central Roast in 2012: 2 wds. |
| 52% | CAROLCHANNING | 13 | Singer/actress who headlined the original production of "Hello, Dolly!" in 1964: 2 wds. |
| 52% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 52% | BOBDYLAN | 8 | "Blowin' in the Wind" singer whose image appears on the cover of the Beatles' "Sgt. Pepper's Lonely Hearts Club Band" album: 2 wds. |
| 51% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 51% | DIANA | 5 | Princess who was the subject of "Candle in the Wind" |
| 51% | MARLONBRANDO | 12 | "The Godfather" actor who played 41-Across in the original 1940s stage production of "A Streetcar Named Desire": 2 wds. |
| 51% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 51% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 51% | STEPHENHAWKING | 14 | ALS-stricken English physicist who's the subject of "The Theory of Everything": 2 wds. |
| 50% | BOBDYLAN | 8 | "Blowin' in the Wind" singer-songwriter who was awarded the Nobel Prize in Literature in the year 2016: 2 wds. |
| 50% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 50% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 50% | GLORIASTEINEM | 13 | Ms. magazine cofounder who's the subject of a new biographical film: 2 wds. |
| 50% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |