| 100% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 42% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 39% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 39% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 39% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 37% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 37% | SHERYLCROW | 10 | "All I Wanna Do" singer who once taught elementary school music: 2 wds. |
| 36% | SHERYLCROW | 10 | "All I Wanna Do" singer who performed the theme to "Tomorrow Never Dies": 2 wds. |
| 36% | SHERYLCROW | 10 | "All I Wanna Do" singer who sang backup for Michael Jackson and Stevie Wonder: 2 wds. |
| 36% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 36% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 35% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 35% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 34% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 33% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 32% | PAULMCCARTNEY | 13 | Singer who came up with "Yesterday" in his sleep: 2 wds. |
| 32% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 32% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 32% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 31% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 31% | JASONISBELL | 11 | Drive-By Truckers singer who appeared on "The Big Interview with Dan Rather" with his wife, singer/songwriter Amanda Shires (2 wds.) |
| 31% | ELTONJOHN | 9 | Pop star who sang a duet with Lady Gaga on his hit "Your Song" at the 2010 Grammys: 2 wds. |
| 31% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 31% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 31% | MEATLOAF | 8 | Rock singer who played Eddie in "The Rocky Horror Picture Show": 2 wds. |
| 31% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 31% | THEWEEKND | 9 | "The Hills" R&B singer who got his seventh #1 hit with 38-Across: 2 wds. |
| 31% | JOHNLEGEND | 10 | "All of Me" R&B singer who sold his music catalog in 2022: 2 wds. |
| 30% | OZZYOSBOURNE | 12 | Heavy metal singer who starred in a 2002-2005 MTV reality show about his family: 2 wds. |
| 30% | NIALLHORAN | 10 | One Direction singer who's in his second season as a coach on "The Voice": 2 wds. |