| 100% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 56% | LAURYNHILL | 10 | Singer whose 1998 song "Doo Wop (That Thing)" debuted at #1: 2 wds. |
| 47% | BRITNEYSPEARS | 13 | Singer whose 2011 song "Hold It Against Me" debuted at #1: 2 wds. |
| 46% | DION | 4 | Celine ___, singer whose song "My Heart Will Go On" won the Grammy for Record of the Year in 1999 |
| 45% | TOBYKEITH | 9 | "Red Solo Cup" singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 45% | KENNYCHESNEY | 12 | "The Good Stuff" singer whose songs have spent 72 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 45% | TIMMCGRAW | 9 | "It's Your Love" singer whose songs have spent 73 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 44% | 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.) |
| 43% | BJTHOMAS | 8 | Singer whose "Raindrops Keep Fallin' on My Head" was the first "Billboard" #1 hit of the 1970s (2 wds.) |
| 43% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 43% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 43% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 43% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 42% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 42% | DION | 4 | "My Heart Will Go On" singer |
| 42% | 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. |
| 42% | DION | 4 | "My Heart Will Go On" singer Celine |
| 42% | DION | 4 | "My Heart Will Go On" singer Celine ___ |
| 42% | CELINE | 6 | "My Heart Will Go On" singer ___ Dion |
| 42% | DION | 4 | “My Heart Will Go On” singer Céline |
| 41% | DION | 4 | Celine ___, "My Heart Will Go On" singer |
| 41% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 41% | DEMILOVATO | 10 | Singer whose 2009 album "Here We Go Again" hit #1 when she was 16: 2 wds. |
| 41% | RANDYNEWMAN | 11 | Singer whose song "I Love L.A." is played after home victories at Dodgers Stadium (2 wds.) |
| 41% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 41% | OLIVIARODRIGO | 13 | Singer whose debut single "Drivers License" reached #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 41% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 41% | TONESANDI | 9 | Australian singer whose "Dance Monkey" was the #2 song on Spotify in 2020: 3 wds. |
| 40% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 40% | MARIAHCAREY | 11 | "Honey" singer who's had three songs debut at #1 on the Billboard Hot 100: 2 wds. |