| 100% | ELTONJOHN | 9 | "Your Song" singer whose charitable foundation helps people with AIDS: 2 wds. |
| 37% | ALEXSMITH | 9 | Chiefs quarterback whose charitable foundation sponsors adult transition programs for foster teens: 2 wds. |
| 37% | MATTDAMON | 9 | "The Martian" actor whose charitable foundation provides drinking water in developing regions: 2 wds. |
| 37% | LAURYNHILL | 10 | Singer whose 1998 song "Doo Wop (That Thing)" debuted at #1: 2 wds. |
| 37% | BRITNEYSPEARS | 13 | Singer whose 2011 song "Hold It Against Me" debuted at #1: 2 wds. |
| 37% | JANISJOPLIN | 11 | Singer whose 1971 song "Me and Bobby McGee" hit #1 posthumously: 2 wds. |
| 37% | LAURABUSH | 9 | Former First Lady whose charitable foundation supports school libraries: 2 wds. |
| 36% | TIMMCGRAW | 9 | "It's Your Love" singer whose songs have spent 73 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 36% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 36% | TAYLORSWIFT | 11 | Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart: 2 wds. |
| 36% | SELENAGOMEZ | 11 | Singer whose 2015 album "Revival" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 35% | DUALIPA | 7 | Pop singer whose "Levitating" was Billboard's best-performing song of 2021: 2 wds. |
| 35% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 35% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 35% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 35% | ROBINTHICKE | 11 | "Blurred Lines" singer whose 2013 song "Give It 2 U" features 31-Across: 2 wds. |
| 35% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 35% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 35% | JOHNDENVER | 10 | "Annie's Song" singer whose surname is Colorado's capital: 2 wds. |
| 35% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 35% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 35% | TONIBRAXTON | 11 | "Un-Break My Heart" singer whose obsession with home decor led to unmanageable debt: 2 wds. |
| 34% | PAULMCCARTNEY | 13 | Singer whose character shrank in 1965's "Help!": 2 wds. |
| 34% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 34% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 34% | HELENREDDY | 10 | Australian-American singer whose 1972 song became an anthem for the women's liberation movement: 2 wds. |
| 34% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 33% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 33% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 33% | KARENCARPENTER | 14 | "We've Only Just Begun" singer whose last name means "a person who makes things from wood": 2 wds. |