| 100% | BRITNEYSPEARS | 13 | "Baby One More Time" pop singer who cameoed in "The Simpsons" episode, "The Mansion Family" as herself: 2 wds. |
| 57% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 52% | MICKJAGGER | 10 | "The Rolling Stones" lead singer who cameoed in "The Simpsons" episode, "How I Spent My Strummer Vacation" as himself: 2 wds. |
| 48% | KATY | 4 | "Firework" pop singer, ___ Perry, who cameoed in "The Simpsons" episode, "The Fight Before Christmas" as herself |
| 48% | LEA | 3 | "Glee" actress and singer, ___ Michele, who cameoed in "The Simpsons" episode, "Elementary School Musical" as herself |
| 46% | CYNDI | 5 | "True Colors" singer, ___ Lauper, who cameoed in "The Simpsons" episode, "Wild Barts Can't Be Broken" as herself |
| 45% | PAUL | 4 | The Beatles co-lead singer, ___ McCartney, who cameoed in "The Simpsons" episode, "Lisa the Vegetarian" as himself |
| 42% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 42% | BRITNEYSPEARS | 13 | Musician whose first single "... Baby one more time" topped the charts in 1998 when she was just 17 years old: 2 wds. |
| 41% | ROBREINER | 9 | "All in the Family" costar who guest-starred as himself on "The Simpsons": 2 wds. |
| 41% | TOM | 3 | "Free Fallin" singer, ___ Petty, who cameoed in "The Simpsons" episode, "How I Spent My Strummer Vacation" as himself |
| 40% | ARIANAGRANDE | 12 | Pop singer and former Nickelodeon star who both hosted "SNL" and performed as the musical guest in 2016: 2 wds. |
| 39% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 39% | LADYGAGA | 8 | "Born This Way" singer who guest-starred as herself on "The Simpsons": 2 wds. |
| 38% | MANDYMOORE | 10 | "I See the Light" singer who voiced Tabitha Vixx in "The Simpsons" episode, "Marge and Homer Turn a Couple Play": 2 wds. |
| 38% | PETERBENCHLEY | 13 | Author of "Jaws" who cameoed as a reporter in the 1975 film adaptation: 2 wds. |
| 38% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 38% | KANYEWEST | 9 | "My Beautiful Dark Twisted Fantasy" artist who cameoed in the movie "The Love Guru" as himself: 2 wds. |
| 36% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 36% | JANETJACKSON | 12 | Actress and singer who played the Evans family's neighbor Penny on "Good Times": 2 wds. |
| 36% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 36% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 36% | FANNIEFLAGG | 11 | Author of "Fried Green Tomatoes at the Whistle Stop Cafe" who cameoed as a teacher in the 1991 film adaptation: 2 wds. |
| 36% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 36% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 35% | SPEARS | 6 | The surname of Baby One More Time singer |
| 35% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 35% | KATYPERRY | 9 | "Roar" singer who had a guest appearance in "HIMYM" in the episode "Oh Honey" : 2 wds. |
| 35% | AUSTINBUTLER | 12 | "Once Upon a Time in Hollywood" actor who starred as Elvis Presley in the 2022 biopic "Elvis": 2 wds. |
| 35% | BILLIEEILISH | 12 | "Bad Guy" singer who was one of PETA's Most Beautiful Vegan Celebrities in 2021: 2 wds. |