| 100% | CHRISTOMLIN | 11 | Grammy-winning contemporary Christian musician who provides vocals for 36-Across's "Be a Light" (2 wds.) |
| 63% | HILLARYSCOTT | 12 | Lead singer of Lady A who provides vocals for 36-Across's "Be a Light" (2 wds.) |
| 39% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 37% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 36% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 36% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 36% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 36% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 35% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 34% | JOEYCHEEK | 9 | 2006 gold medalist who's been a speed skating commentator for NBC's Olympic telecasts: 2 wds. |
| 34% | TARALIPINSKI | 12 | 1998 gold medalist who's been a figure skating commentator for NBC's Olympic telecasts: 2 wds. |
| 34% | DAVEGROHL | 9 | American musician who was the drummer for Nirvana and lead vocalist of Foo Fighters: 2 wds. |
| 34% | JANETWEISS | 10 | American musician who was the drummer for bands like Sleater-Kinney and Wild Flag: 2 wds. |
| 34% | NEWLEY | 6 | Anthony who won a Grammy for "What Kind of Fool Am I?" |
| 33% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 33% | BOBBY | 5 | ___ Darin, "Mack the Knife" musician who was 22 when he won the 1959 Grammy for Record of the Year |
| 32% | SHARYNALFONSI | 13 | Investigative journalist who is a correspondent for "60 Minutes": 2 wds. |
| 32% | ALICIAKEYS | 10 | American musician who co-founded and is the Global Ambassador of the nonprofit organization "Keep a Child Alive": 2 wds. |
| 32% | THUG | 4 | Rapper Young ___, one of the musicians who won the 2019 Grammy Award for Song of the Year for "This Is America" |
| 32% | IRENE | 5 | Singer Cara who won a Grammy for best female pop vocal performance for "Flashdance ... What a Feeling" |
| 32% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 32% | ARLENEFRANCIS | 13 | She was a regular panelist on 18-Across for 25 years: 2 wds. |
| 32% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 32% | APOLOOHNO | 9 | 2002 & 2006 gold medalist who's been a short track commentator for NBC's Olympic telecasts: 2 wds. |
| 31% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 31% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 31% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 31% | JACKNICKLAUS | 12 | Golfer who is tied with 18-Across for the most consecutive seasons (17) with a PGA win (2 wds.) |
| 31% | ARNOLDPALMER | 12 | Golfer who is tied with 43-Across for the most consecutive seasons (17) with a PGA win (2 wds.) |
| 31% | BLUEBAYOU | 9 | Roy Orbison song that was a #3 hit for 32-Across in 1977: 2 wds. |