| 100% | MARTYROBBINS | 12 | Singer whose "El Paso" was the first "Billboard" #1 hit of the 1960s (2 wds.) |
| 67% | BJTHOMAS | 8 | Singer whose "Raindrops Keep Fallin' on My Head" was the first "Billboard" #1 hit of the 1970s (2 wds.) |
| 61% | KCANDTHE | 8 | With 40-Across, group whose "Please Don't Go" was the first "Billboard" #1 hit of the 1980s (3 wds.) |
| 60% | JACKSONBROWNE | 13 | "Doctor, My Eyes" singer whose first name is the capital of Mississippi: 2 wds. |
| 59% | GWENSTEFANI | 11 | Singer whose 2005 #1 hit "Hollaback Girl" was produced by Pharrell Williams as half of the Neptunes: 2 wds. |
| 57% | ELVISPRESLEY | 12 | Singer known as the "The King of Rock and Roll" whose first hit singles were with Sun Records (2 wds.) |
| 55% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 55% | CARLPERKINS | 11 | Singer known as "The King of Rockabilly" whose first hit singles were with Sun Records (2 wds.) |
| 54% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 54% | TAYLORSWIFT | 11 | Singer whose "Eras Tour" is the highest-grossing concert tour of all time: 2 wds. |
| 53% | HARRYSTYLES | 11 | Singer whose "As It Was" was the best-selling global single of 2022: 2 wds. |
| 53% | STEVIEWONDER | 12 | Soul singer whose 1976 album "Songs in the Key of Life" spent its first 13 weeks atop the Billboard 200: 2 wds. |
| 53% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 53% | BENSONBOONE | 11 | Singer whose "Beautiful Things" was the best-selling global single of 2024: 2 wds. |
| 52% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 52% | EDSHEERAN | 9 | Singer whose "÷ Tour" is the fourth highest-grossing concert tour of all time: 2 wds. |
| 52% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 52% | MORGANWALLEN | 12 | "7 Summers" country singer whose "You Proof" hit the Billboard Top 10 in 2022: 2 wds. |
| 52% | CHUBBYCHECKER | 13 | Rock singer whose version of "The Twist" inspired a dance craze in the 1960s: 2 wds. |
| 52% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 52% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 52% | MARGARETCHO | 11 | Comedian who was the Poodle on season 1 of "The Masked Singer": 2 wds. |
| 52% | IGGYAZALEA | 10 | "Fancy" singer who is one of only two music acts to have their first two hit singles rank #1 and #2 simultaneously on the U.S. "Billboard" Hot 100 chart (2 wds.) |
| 51% | JOEYFATONE | 10 | Former 'N Sync singer whose first name is also the term for a baby kangaroo: 2 wds. |
| 51% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 51% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 51% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 51% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 51% | ALGREEN | 7 | Singer whose name is an anagram of the word "general": 2 wds. |
| 51% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |