| 100% | STAPLETON | 9 | Grammy winner Chris whose album "From a Room: Volume 2" was released on December 1 |
| 33% | 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.) |
| 32% | MARIAHCAREY | 11 | Five-time Grammy winner who is the only artist whose first five singles reached #1 on the Billboard Hot 100 (2 wds.) |
| 31% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 31% | ROOM | 4 | "From A ___: Volume 1" country album by Chris Stapleton that won a Grammy Award in 2018 |
| 31% | INDIAARIE | 9 | Grammy winner whose first name is also a country |
| 31% | JOHNLEGEND | 10 | "Ordinary People" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 30% | THISMOMENT | 10 | "From ___ On," a hit song by Shania Twain, whose birthday it is today: 2 wds. |
| 30% | JONASBROTHERS | 13 | Artists on "Songland" whose "Sucker" was a #1 Billboard hit in 2019: 2 wds. |
| 30% | JUNECARTERCASH | 14 | "Ring of Fire" songwriter and five-time Grammy winner whose first name is a month of the year (2 wds.) |
| 29% | TONIBRAX | 8 | Multiple Grammy winner who was a contestant on "Dancing With the Stars" |
| 29% | REBAMCENTIRE | 12 | "Sing It Now: Songs of Faith & Hope" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 28% | DELREY | 6 | Singer Lana whose 2017 album "Lust for Life" was nominated for a Best Pop Vocal Album Grammy (2 wds.) |
| 28% | UNSNAG | 6 | Release from being caught on a nail, say |
| 28% | LIVINGHISTORY | 13 | Memoir by 31-Across whose audiobook version was nominated for a Grammy Award for Best Spoken Word Album (2 wds.) |
| 27% | EDSHEERAN | 9 | Grammy Award-winning singer-songwriter whose three album releases have been named after mathematical symbols |
| 27% | KELLYCLARKSON | 13 | "American Idol" winner whose newest album is titled "Meaning of Life": 2 wds. |
| 27% | CARLOSSANTANA | 13 | Latin Grammy award winner who teaches a MasterClass course on guitar: 2 wds. |
| 27% | MACMILLER | 9 | "Good News" rapper whose surname is a beer brand from Milwaukee: 2 wds. |
| 27% | MIRANDALAMBERT | 14 | "Wildcard" Best Country Album Grammy winner who was born on November 10, 1983 (2 wds.) |
| 27% | HESAID | 6 | Song by Group 1 Crew from the album "Fearless" featuring Chris August: 2 wds. |
| 27% | LAYLA | 5 | Song on Eric Clapton's "Unplugged" album whose title is a woman's name |
| 27% | ALECGUINNESS | 12 | Obi-Wan Kenobi portrayer whose surname is a beer brand from Ireland: 2 wds. |
| 27% | IWILL | 5 | "___ Wait," Mumford & Sons track released as a lead single from their album "Babel": 2 wds. |
| 27% | CHUBBYCHECKER | 13 | Singer born Ernest Evans whose stage name is a variation on "Fats Domino": 2 wds. |
| 26% | KOBEBRYANT | 10 | Former L.A. Laker whose jersey number was retired during a December 18 ceremony: 2 wds. |
| 26% | MIDDLECHILD | 11 | J. Cole single from the album "Revenge of the Dreamers III" that was nominated for a Best Rap Performance Grammy Award in 2020 (2 wds.) |
| 26% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 26% | TALK | 4 | Hit song by Khalid from his album "Free Spirit" which was nominated for a Grammy in 2020 |
| 26% | LOCATION | 8 | Debut single by Khalid from his album "American Teen" which was nominated for a Grammy in 2018 |