| 100% | SHERYLCROW | 10 | "All I Wanna Do" singer who once taught elementary school music: 2 wds. |
| 56% | SHERYLCROW | 10 | "All I Wanna Do" singer who performed the theme to "Tomorrow Never Dies": 2 wds. |
| 55% | SHERYLCROW | 10 | "All I Wanna Do" singer who sang backup for Michael Jackson and Stevie Wonder: 2 wds. |
| 54% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 53% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 49% | CROW | 4 | Sheryl ___, "All I Wanna Do" singer who worked as a music teacher |
| 40% | SHERYL | 6 | Crow, American singer who sang All I Wanna Do |
| 40% | JOHNLEGEND | 10 | "All of Me" R&B singer who sold his music catalog in 2022: 2 wds. |
| 39% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 38% | JESSEWILLIAMS | 13 | "Grey's Anatomy" costar who once taught high school English and African studies: 2 wds. |
| 37% | TAYLORSWIFT | 11 | "Look What You Made Me Do" singer who has won the most Billboard Music Awards (23) (2 wds.) |
| 37% | SHERYLCROW | 10 | "All I Wanna Do" singer, 1994 |
| 37% | CROW | 4 | "All I Wanna Do" singer Sheryl |
| 37% | SHERYL | 6 | "All I Wanna Do" singer Crow |
| 37% | SHERYLC | 7 | "All I Wanna Do" singer-songwriter |
| 37% | SHERYLCROWS | 11 | “All I Wanna Do” singer boasts? |
| 36% | BILLYJOEL | 9 | "Piano Man" singer who once boxed on the Golden Gloves circuit: 2 wds. |
| 36% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 36% | MARIAHCAREY | 11 | "I'll Be There" pop singer who once had the alter ego "Mimi": 2 wds. |
| 35% | LEANNRIMES | 10 | "How Do I Live" singer who won the fourth season of "The Masked Singer" as the Sun: 2 wds. |
| 35% | BRITNEYSPEARS | 13 | "Hold It Against Me" singer who was on "The All-New Mickey Mouse Club": 2 wds. |
| 35% | JOHNLEGEND | 10 | "All of Me" singer who has his own wine label, LVE: 2 wds. |
| 35% | ALICIAKEYS | 10 | "Fallin'" singer who teaches a MasterClass course in songwriting and producing: 2 wds. |
| 34% | EZRAKOENIG | 10 | Vampire Weekend lead vocalist who once taught junior high English: 2 wds. |
| 34% | CHUBBYCHECKER | 13 | 76-year-old singer who is still doing "The Twist": 2 wds. |
| 34% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 34% | PAULSIMON | 9 | Singer who performed "Still Crazy After All These Years" on the SNL40 anniversary special: 2 wds. |
| 33% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 33% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 33% | JOHNLEGEND | 10 | "All of Me" singer who sang backup for Alicia Keys and Kanye West: 2 wds. |