| 100% | SAMSMITH | 8 | British crooner who followed up his Grammy-winning debut album with "The Thrill of It All": 2 wds. |
| 40% | 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% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 36% | 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.) |
| 34% | CHAPPELLROAN | 12 | Singer with the debut album "The Rise and Fall of a Midwest Princess": 2 wds. |
| 34% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 34% | PAULMCCARTNEY | 13 | Artist with the most number of Grammy nominations in one night without winning, with 9: 2 wds. |
| 32% | EDGARMARTINEZ | 13 | Hall of Famer with the Mariners who played 68% of his games as a designated hitter: 2 wds. |
| 31% | LESMISERABLES | 13 | Musical with the song "I Dreamed a Dream" which was also the name of Scottish singer Susan Boyle's (birthday today) debut album: 2 wds. |
| 31% | 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.) |
| 31% | DERRICKTHOMAS | 13 | NFL pass rusher who played his entire career with the Kansas City Chiefs and is considered one of the greatest of all time: 2 wds. |
| 30% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 30% | PRIVATEDANCER | 13 | 1984 Tina Turner album with the #1 hit "What's Love Got to Do With It": 2 wds. |
| 30% | PAULMOLITOR | 11 | Hall of Famer with the Brewers, Blue Jays, and Twins who played 44% of his games as a designated hitter: 2 wds. |
| 29% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 29% | BECK | 4 | Artist who won the 2014 Album of the Year Grammy |
| 29% | COHEN | 5 | Leonard ___, musician who received critical acclaim at the age of 33, following his debut album with Columbia Records |
| 29% | JIMBOEHEIM | 10 | College basketball coach who has won 946 games with the Syracuse Orange as of 3/20/19: 2 wds. |
| 29% | FEDUP | 5 | Sick of it all: 2 wds. |
| 29% | DEREKHOUGH | 10 | "Dancing With the Stars" dancer who's a judge on "World of Dance": 2 wds. |
| 29% | FRANKTHOMAS | 11 | Hall of Famer with the White Sox, Blue Jays, and A's who played 56% of his games as a designated hitter: 2 wds. |
| 29% | BECK | 4 | His "Morning Phase" won the Album of the Year Grammy in February 2015 |
| 29% | SARAHSTOREY | 11 | British paralympian who has won 16 medals at the Paralympic games: 2 wds. |
| 29% | JOCELYNALO | 10 | Softball player who won two championships with the University of Oklahoma and who is both the NCAA's all-time home run leader and the only player to record three 30-home run seasons (2 wds.) |
| 29% | SKEPTA | 6 | British hip-hop star who won the 2016 Mercury Prize for his album Konnichiwa |
| 29% | LUTHERVANDROSS | 14 | His "Dance With My Father" won the 2003 Grammy for Song of the Year |
| 29% | BEYONCE | 7 | Singer who won the Album of the Year Grammy for "Cowboy Carter" |
| 29% | BIGMISTAKE | 10 | Song by Australian singer-songwriter Natalie Imbruglia from her debut album "Left of the Middle": 2 wds. |
| 29% | ALFONSORIBEIRO | 14 | "Dancing With the Stars" host who played one of Ricky's friends on 19-Across: 2 wds. |
| 29% | NAS | 3 | Rapper who won his first Grammy for the 2020 album “King’s Disease” |