| 100% | SHERYLCROW | 10 | "All I Wanna Do" singer who sang backup for Michael Jackson and Stevie Wonder: 2 wds. |
| 54% | JOHNLEGEND | 10 | "All of Me" singer who sang backup for Alicia Keys and Kanye West: 2 wds. |
| 47% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 45% | SHERYLCROW | 10 | "All I Wanna Do" singer who once taught elementary school music: 2 wds. |
| 44% | SHERYLCROW | 10 | "All I Wanna Do" singer who performed the theme to "Tomorrow Never Dies": 2 wds. |
| 43% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 38% | SHERYL | 6 | Crow, American singer who sang All I Wanna Do |
| 34% | CROW | 4 | Sheryl ___, "All I Wanna Do" singer who worked as a music teacher |
| 33% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 32% | NANCYSINATRA | 12 | "Somethin' Stupid" singer who also sang 1965's "These Boots Are Made for Walkin'": 2 wds. |
| 32% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 32% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 32% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 32% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 31% | DOLLYPARTON | 11 | "Jolene" singer who wrote the music and lyrics for the Broadway musical "9 to 5": 2 wds. |
| 31% | ELVISPRESLEY | 12 | American singer who acted in "Love Me Tender" and has sold 200 million records worldwide: 2 wds. |
| 31% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 31% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 31% | CROW | 4 | Sheryl who sings "All I Wanna Do" |
| 31% | WHITNEY | 7 | With 33-Across, "So Emotional" singer who sang backup for Chaka Khan and Lou Rawls |
| 31% | RENEEFLEMING | 12 | Opera singer who sang the national anthem at the Super Bowl in 2014 and received the National Medal of Arts in 2012: 2 wds. |
| 30% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 30% | TAYLORSWIFT | 11 | American singer who has made hits like "You Belong With Me," and is currently dating British actor Joe Alwyn: 2 wds. |
| 30% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 30% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 30% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 30% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 30% | JIMMYFALLON | 11 | Late-night host who sings "All I Want for Christmas Is You" with Dolly Parton on "A Holly Dolly Christmas" (2 wds.) |
| 30% | BILLYJOEL | 9 | "Piano Man" singer who sang "Uptown Girl": 2 wds. |
| 30% | SHERYL | 6 | ___ Crow who sang "All I Wanna Do" |