| 100% | THEWEEKND | 9 | "Earned It" R&B singer who headlined at the 2018 Coachella Festival: 2 wds. |
| 65% | JACKWHITE | 9 | "Lazaretto" rock singer who headlined at the 2015 Coachella Festival: 2 wds. |
| 58% | DIANAROSS | 9 | R&B singer who headlined the Essence Festival in New Orleans on June 30: 2 wds. |
| 48% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 45% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 44% | LIONELRICHIE | 12 | "Dancing on the Ceiling" R&B singer who's been a judge on "American Idol" since 2018: 2 wds. |
| 44% | LADY | 4 | With 39-Across, "Born This Way" pop singer who headlined at the 2017 Coachella Festival |
| 44% | VICTORIAMONET | 13 | "On My Mama" R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| 43% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 42% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 41% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 40% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 39% | HER | 3 | One-named R&B singer who performed "U Got It Bad" with Usher at the 2024 Super Bowl halftime show |
| 39% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 39% | CALVIN | 6 | With 33-Across, EDM DJ who headlined at the 2016 Coachella Festival |
| 39% | JANETJACKSON | 12 | "Rhythm Nation" R&B singer who received the 1990 MTV Video Vanguard Award, the first African American woman to do so: 2 wds. |
| 38% | MICHELLEWOLF | 12 | Netflix host who performed at the 2018 White House Correspondents' Dinner: 2 wds. |
| 38% | MORGANWALLEN | 12 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Broadway Girls" with Lil Durk: 2 wds. |
| 38% | ANDRADAY | 8 | Singer who performed "Stand Up for Something" at the 2018 Oscars, accompanied by Common and various activists: 2 wds. |
| 38% | NATKINGCOLE | 11 | R&B singer who's the father of singer Natalie: 3 wds. |
| 38% | SILKSONIC | 9 | R & B duo who performed their #1 single "Leave the Door Open" at the Grammy Awards ceremony in 2021 (2 wds.) |
| 38% | BILLYRAYCYRUS | 13 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Old Town Road" with Lil Nas X: 2 wds. |
| 38% | JANELLEMONAE | 12 | R&B singer who plays mathematician Mary Jackson in "Hidden Figures": 2 wds. |
| 37% | CAROLCHANNING | 13 | Singer/actress who headlined the original production of "Hello, Dolly!" in 1964: 2 wds. |
| 37% | JUSTINBIEBER | 12 | Pop/R&B singer who's also topped the Country chart, thanks to "10,000 Hours" with Dan + Shay: 2 wds. |
| 37% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 37% | LUKEBRYAN | 9 | "Play It Again" country singer who sang the National Anthem at the 2017 Super Bowl: 2 wds. |
| 37% | THEWEEKND | 9 | "The Hills" R&B singer who got his seventh #1 hit with 38-Across: 2 wds. |
| 37% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 37% | DOLLYPARTON | 11 | Country singer who received the Gary Haber Lifting Lives Award at the 11th Annual ACM Honors: 2 wds. |