| 100% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 66% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |
| 59% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 58% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 57% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 56% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 56% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 56% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 56% | MARCANTHONY | 11 | Ex-husband of Jennifer Lopez who won a Grammy for "Amar Sin Mentiras": 2 wds. |
| 55% | BILLIEEILISH | 12 | "Bad Guy" singer who won a record five Grammy Awards in 2020, including Best New Artist (2 wds.) |
| 55% | JONSTEWART | 10 | Former "Daily Show" host who won a Spoken Word Grammy for "Earth (The Audiobook)": 2 wds. |
| 55% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 55% | JAMESTAYLOR | 11 | Ex-husband of Carly Simon who won a Grammy for "You've Got a Friend": 2 wds. |
| 55% | MIRANDALAMBERT | 14 | Ex-wife of Blake Shelton who won a Grammy for "The House That Built Me": 2 wds. |
| 55% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 55% | RACHELMADDOW | 12 | MSNBC host who won a 2021 Grammy for the audiobook of her nonfiction book "Blowout": 2 wds. |
| 54% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 54% | JOANRIVERS | 10 | Late "Fashion Police" host who won a Spoken Word Grammy for "Diary of a Mad Diva": 2 wds. |
| 54% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 54% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 53% | PATTONOSWALT | 12 | "A.P. Bio" actor who won a Grammy for Best Comedy Album in 2017: 2 wds. |
| 53% | BETTYWHITE | 10 | "The Proposal" actress who won a Grammy for the spoken word recording of her book "If You Ask Me": 2 wds. |
| 53% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 52% | JOANRIVERS | 10 | "Fashion Police" host who won a Grammy for a spoken word recording of her book "Diary of a Mad Diva": 2 wds. |
| 52% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 52% | DONCHEADLE | 10 | "Hotel Rwanda" actor who won a 2022 Grammy for the audiobook of John Lewis's "Carry On": 2 wds. |
| 52% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 52% | ANDERSONPAAK | 12 | LA hip-hop artist who won a 2019 Grammy for Best Rap Performance for "Bubblin": 2 wds. |
| 52% | SIDNEYPOITIER | 13 | "Lilies of the Field" actor who won a Grammy for the spoken word recording of his book "The Measure of a Man": 2 wds. |
| 51% | VIOLADAVIS | 10 | "The Woman King" actress who won a 2023 Grammy for the audiobook of her memoir "Finding Me": 2 wds. |