| 100% | ELVISCOSTELLO | 13 | Singer who recorded the 2013 album "Wise Up Ghost" with the Roots: 2 wds. |
| 47% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 46% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 44% | 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. |
| 44% | 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. |
| 43% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 43% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 43% | MEGHANTRAINOR | 13 | "All About That Bass" singer-songwriter who recorded the duet "White Christmas" with 32-Across (2 wds.) |
| 43% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 42% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 42% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 41% | KATYPERRY | 9 | "Roar" singer who's #11 on the 2013 Maxim Hot 100 List: 2 wds. |
| 41% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 41% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 41% | JOHNFOGERTY | 11 | Creedence Clearwater Revival singer who appeared on "The Big Interview with Dan Rather" with his children, who recorded an album with him in 2020 (2 wds.) |
| 41% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 41% | PAULMCCARTNEY | 13 | Singer who came up with "Yesterday" in his sleep: 2 wds. |
| 41% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 41% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 41% | SAMSMITH | 8 | British crooner who followed up his Grammy-winning debut album with "The Thrill of It All": 2 wds. |
| 41% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 41% | DAVIDBOWIE | 10 | Singer who featured the glam rocker character Ziggy Stardust on his 1972 concept album: 2 wds. |
| 40% | JANELLEMONAE | 12 | Singer who featured the android character Cindi Mayweather on her 2010 "The ArchAndroid" concept album: 2 wds. |
| 40% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 40% | JESSEMCCARTNEY | 14 | Pop singer with Dream Street who was the runner-up on season 3 of "The Masked Singer" as the Turtle: 2 wds. |
| 40% | JENNIFERLOPEZ | 13 | "On the Floor" singer who has Puerto Rican roots: 2 wds. |
| 40% | GLORIAESTEFAN | 13 | "Turn the Beat Around" singer who has Cuban roots: 2 wds. |
| 40% | EARLSWEATSHIRT | 14 | "Top" American rapper with the 2013 hit album "Doris": 2 wds. |
| 40% | THECIVILWARS | 12 | Duo who recorded 18-Across, or the title of their 2013 album: 3 wds. |
| 40% | BILLNYE | 7 | TV "Science Guy" who appeared on "Dancing With the Stars" in 2013: 2 wds. |