| 100% | KACEYMUSGRAVES | 14 | Artist whose album "Golden Hour" won Album of the Year at the 2019 Grammys: 2 wds. |
| 64% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 61% | SIMONEMANUEL | 12 | Two-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2019 Golden Goggle Awards: 2 wds. |
| 59% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 58% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 56% | JONASBROTHERS | 13 | 2008 American Music Awards New Artist of the Year whose fifth studio album, "Happiness Begins," debuted at #1 on the U.S. "Billboard" 200 in 2019 (2 wds.) |
| 55% | BECK | 4 | He won Album of the Year at the 2015 Grammys |
| 54% | CAELEBDRESSEL | 13 | Seven-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards three times: 2 wds. |
| 54% | MICHAELPHELPS | 13 | 23-time Olympic swimming gold medalist who won Athlete of the Year at the Golden Goggle Awards seven times: 2 wds. |
| 53% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 52% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 52% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 52% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 52% | MISSYFRANKLIN | 13 | Five-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2011 and 2012 Golden Goggle Awards: 2 wds. |
| 51% | KATIELEDECKY | 12 | Seven-time Olympic swimming gold medalist who won Female Athlete of the Year at the 2013-2018 and 2021 Golden Goggle Awards: 2 wds. |
| 51% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 51% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 51% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 51% | MARENMORRIS | 11 | Her "Girl" won the 2019 CMA for Album of the Year: 2 wds. |
| 50% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 50% | JUSTINBIEBER | 12 | 2010 American Music Awards New Artist of the Year whose fifth studio album, "Changes," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 50% | ARIANAGRANDE | 12 | 2013 American Music Awards New Artist of the Year whose sixth studio album, "Positions," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 50% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 50% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 50% | FRANKSINATRA | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "September of My Years": 2 wds. |
| 50% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 50% | PAULSIMON | 9 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Bridge over Troubled Water": 2 wds. |
| 50% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 50% | BEYONCE | 7 | 14-Across, 8-Down, and 49-Across singer whose "Cowboy Carter" won Album of the Year at the Grammy Awards in 2025 |
| 49% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |