| 100% | DAVIDBOWIE | 10 | "Space Oddity" singer who cowrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 76% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 70% | LADYANTEBELLUM | 14 | "American Honey" group who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 47% | NICKJONAS | 9 | "Jealous" pop singer who both hosted and was the musical act in a 2021 "SNL" episode: 2 wds. |
| 45% | ALEXNEWELL | 10 | Actor who won a Tony in 2023 for their role as Lulu in the Broadway musical "Shucked": 2 wds. |
| 44% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 43% | PAULMCCARTNEY | 13 | 76-year-old singer who is still in a "Band on the Run": 2 wds. |
| 42% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 42% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 42% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 42% | STEVIEWONDER | 12 | "Sir Duke" singer who debuted songs on the Hot 100 in five different decades: 2 wds. |
| 41% | TINATURNER | 10 | "Private Dancer" singer who has a solo in "We Are the World": 2 wds. |
| 41% | HELLODOLLY | 10 | Broadway musical with the song "It Takes a Woman" (2 wds.) |
| 41% | ARIANAGRANDE | 12 | "7 Rings" singer who was both the host and musical guest on a 2016 "SNL" episode: 2 wds. |
| 41% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 41% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 41% | DIONNEWARWICK | 13 | "Walk On By" singer who has a solo in "We Are the World": 2 wds. |
| 41% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 41% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 41% | KATYPERRY | 9 | "Roar" singer who had a guest appearance in "HIMYM" in the episode "Oh Honey" : 2 wds. |
| 40% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 40% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 40% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 40% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 40% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 40% | BRADLEYCOOPER | 13 | Actor who had a song from "A Star Is Born" chart on the Billboard Hot 100 in 2018: 2 wds. |
| 39% | CELINEDION | 10 | "The Power of Love" singer who was made a Companion of the Order of Canada in 2008: 2 wds. |
| 39% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 39% | ALICIAKEYS | 10 | "Songs in A Minor" singer/songwriter who won the 2021 Audie Award for Narration by the Author for her memoir "More Myself" (2 wds.) |
| 38% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |