| 100% | SAMSMITH | 8 | Grammy-winning singer of "Stay with Me," 15-Across, 20-Across, and 37-Across and the 2017 album "The Thrill of It All" (2 wds.) |
| 66% | SAMSMITH | 8 | Grammy-winning singer of "Stay With Me," 15-Across, 20-Across, and 37-Across (2 wds.) |
| 48% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 48% | SAMSMITH | 8 | British crooner who followed up his Grammy-winning debut album with "The Thrill of It All": 2 wds. |
| 43% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 41% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 40% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 40% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 40% | PALACE | 6 | Sam Smith's single from the 2017 album "The Thrill of It All" |
| 39% | PRAY | 4 | Sam Smith's promotional single from the 2017 album "The Thrill of It All" |
| 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% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 39% | LEONARDCOHEN | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2017 Album of the Year Juno Award for "You Want It Darker" (2 wds.) |
| 39% | CHAPPELLROAN | 12 | Singer with the debut album "The Rise and Fall of a Midwest Princess": 2 wds. |
| 38% | 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. |
| 38% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 38% | EDSHEERAN | 9 | 15-Across, 28-Across, and 35-Across singer whose solo studio albums are all named with mathematical symbols (2 wds.) |
| 38% | CHRISSTAPLETON | 14 | "From a Room: Volume 1" singer who won the 2017 CMA Awards for Male Vocalist of the Year and Album of the Year (2 wds.) |
| 38% | PAULMCCARTNEY | 13 | 15-Across and 31-Across singer/songwriter with 18 Grammy Awards, an Academy Award, and two inductions into the Rock and Roll Hall of Fame who turns 80 years old this week (2 wds.) |
| 37% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 37% | DANCEMONKEY | 11 | 2019 hit for Tones and I with a sign of the Chinese zodiac in its title: 2 wds. |
| 37% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 37% | GIRLONFIRE | 10 | Grammy-winning album by 42-Across with the singles "Brand New Me" and "New Day" (3 wds.) |
| 37% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 37% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 37% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 37% | TODDRUNDGREN | 12 | "Hello It's Me" singer inducted into the Rock and Roll Hall of Fame in 2021: 2 wds. |
| 36% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 36% | SHAWNJOHNSON | 12 | Gymnast who won season 8 and was runner-up in season 15 of "Dancing With the Stars": 2 wds. |
| 36% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |