| 100% | BRITNEYSPEARS | 13 | Singer whose 2011 song "Hold It Against Me" debuted at #1: 2 wds. |
| 57% | LAURYNHILL | 10 | Singer whose 1998 song "Doo Wop (That Thing)" debuted at #1: 2 wds. |
| 51% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 47% | BRITNEYSPEARS | 13 | "Hold It Against Me" singer who was on "The All-New Mickey Mouse Club": 2 wds. |
| 44% | TIMMCGRAW | 9 | "It's Your Love" singer whose songs have spent 73 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 43% | JANISJOPLIN | 11 | Singer whose 1971 song "Me and Bobby McGee" hit #1 posthumously: 2 wds. |
| 43% | BILLYJOEL | 9 | Singer whose 1980 "Glass Houses" album includes the #1 song "It's Still Rock and Roll to Me" (2 wds.) |
| 42% | TOBYKEITH | 9 | "Red Solo Cup" singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 42% | KENNYCHESNEY | 12 | "The Good Stuff" singer whose songs have spent 72 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 41% | TAYLORSWIFT | 11 | "Shake It Off" singer who's had seven songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 41% | RANDYNEWMAN | 11 | Singer whose song "I Love L.A." is played after home victories at Dodgers Stadium (2 wds.) |
| 41% | MILEYCYRUS | 10 | 17-Across and 27-Across singer whose 2023 single "Flowers" debuted at No. 1 on the "Billboard" Global 200 chart in 2023 (2 wds.) |
| 40% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Singer whose "Oops! ... I Did It Again" album went platinum in one week: 2 wds. |
| 40% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 39% | ROBINTHICKE | 11 | "Blurred Lines" singer whose 2013 song "Give It 2 U" features 31-Across: 2 wds. |
| 39% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 38% | BEYONCEKNOWLES | 14 | Singer whose song "Crazy In Love" featuring Jay Z peaked at number one on the Billboard Hot 100 chart in 2003: 2 wds. |
| 38% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 37% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 37% | OLIVIARODRIGO | 13 | Singer whose debut single "Drivers License" reached #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 37% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 37% | BRITNEYSPEARS | 13 | "Hold It Against Me" singer |
| 37% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 37% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 37% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 37% | MARIAHCAREY | 11 | "Honey" singer who's had three songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 37% | BRITNEY | 7 | "Hold It Against Me" singer Spears |
| 36% | CELESTE | 7 | Singer whose album Not Your Muse debuted at No. 1 |
| 36% | KELLYCLARKSON | 13 | Singer whose debut single "A Moment Like This" reached #1 on the Billboard Hot 100 in 2002: 2 wds. |