| 100% | MARTINAMCBRIDE | 14 | "In My Daughter's Eyes" country singer who has never won a Grammy despite 14 nominations: 2 wds. |
| 62% | KATYPERRY | 9 | "Dark Horse" pop singer who has never won a Grammy despite 13 nominations: 2 wds. |
| 55% | SNOOPDOGG | 9 | "Drop It Like It's Hot" rapper who has never won a Grammy despite 17 nominations: 2 wds. |
| 40% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 40% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 40% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 39% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 38% | RAYCHARLES | 10 | "Hit the Road Jack" singer who has a solo in 1985's "We Are the World": 2 wds. |
| 38% | REBAMCENTIRE | 12 | Red-haired country singer who's in her first season as a coach on "The Voice": 2 wds. |
| 37% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 37% | ALISONKRAUSS | 12 | "When You Say Nothing at All" country singer who has won 27 Grammys: 2 wds. |
| 37% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 36% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 36% | TINATURNER | 10 | "Private Dancer" singer who has a solo in "We Are the World": 2 wds. |
| 36% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 36% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 36% | DIONNEWARWICK | 13 | "Walk On By" singer who has a solo in "We Are the World": 2 wds. |
| 36% | FETTYWAP | 8 | "Trap Queen" singer who won 14-Across in 2016: 2 wds. |
| 35% | KATYPERRY | 9 | "Roar" singer who had a guest appearance in "HIMYM" in the episode "Oh Honey" : 2 wds. |
| 35% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 35% | SAMSMITH | 8 | "Stay With Me" singer who won 14-Across in 2015: 2 wds. |
| 35% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 35% | GLENCAMPBELL | 12 | "Rhinestone Cowboy" singer who recently won the Best Country Song Grammy: 2 wds. |
| 35% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 35% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 35% | REBAMCENTIRE | 12 | Grammy-winning country star who plays a singer on 32-Across: 2 wds. |
| 35% | DEBBYBOONE | 10 | "You Light Up My Life" singer who won the Best New Artist Grammy in 1978: 2 wds. |
| 35% | TAYLORSWIFT | 11 | Country singer who had a crossover hit with her 2008 pop song "Love Story" (2 wds.) |
| 35% | SALLYFIELD | 10 | Actress who had a 28-year gap between Oscar nominations for 1984's "Places in the Heart" and 2012's "Lincoln": 2 wds. |
| 34% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who has won two "Billboard" Music Awards and a "Billboard" Women in Music Chart-Topper Award (2 wds.) |