| 100% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 65% | TONESANDI | 9 | Australian singer whose "Dance Monkey" was the #2 song on Spotify in 2020: 3 wds. |
| 51% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 47% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 47% | RODDY | 5 | With 32-Across, American rapper whose "The Box" was the #3 song on Spotify in 2020 |
| 47% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 46% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 45% | ALANNAHMYLES | 12 | Singer whose "Black Velvet" was a #1 song for two weeks in 1990 (2 wds.) |
| 44% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 44% | {THE}WEEKND | 11 | Artist whos song "Blinding Lights" was streamed almost 1.6 billion times on Spotify in 2020 |
| 43% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 43% | SHEERAN | 7 | Singer whose "Shape of You" was the most streamed song of the 2010s on Spotify |
| 43% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 43% | DONNYOSMOND | 11 | Actor who was the Peacock on season 1 of "The Masked Singer": 2 wds. |
| 43% | TORISPELLING | 12 | Actress who was the Unicorn on season 1 of "The Masked Singer": 2 wds. |
| 43% | MARGARETCHO | 11 | Comedian who was the Poodle on season 1 of "The Masked Singer": 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. |
| 42% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 42% | JANETJACKSON | 12 | Singer whose "Escapade" was a #1 song for three weeks in 1990 (2 wds.) |
| 42% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 42% | BJTHOMAS | 8 | Singer whose "Raindrops Keep Fallin' on My Head" was the first "Billboard" #1 hit of the 1970s (2 wds.) |
| 41% | DION | 4 | Celine ___, singer whose song "My Heart Will Go On" won the Grammy for Record of the Year in 1999 |
| 40% | 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. |
| 40% | MILEYCYRUS | 10 | "Party in the U.S.A." singer whose first TV series lead role was on Disney's "Hannah Montana": 2 wds. |
| 40% | DEMILOVATO | 10 | "Heart Attack" singer whose first TV series lead role was on the Disney Channel's "Sonny with a Chance": 2 wds. |
| 40% | TINATURNER | 10 | American singer whose Maracana Stadium concert in 1988 is the third highest-attended ticketed concert for a single artist: 2 wds. |
| 40% | VASCOROSSI | 10 | Italian singer whose Enzo Ferrari Park concert in 2017 is the highest-attended ticketed concert for a single artist: 2 wds. |
| 40% | FLORIDA | 7 | Rapper and singer whose name comes from the state he was born in: 2 wds. |
| 40% | RAYCHARLES | 10 | "What'd I Say" singer whose sunglasses are in the Smithsonian (2 wds.) |
| 40% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |