| 100% | 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. |
| 85% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 84% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 57% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 57% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 54% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 48% | 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.) |
| 47% | FRANKSINATRA | 12 | Actor in the Best Picture winner "From Here to Eternity" who was nominated for seven Album of the Year Grammys: 2 wds. |
| 45% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 44% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |
| 43% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 43% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 43% | BILLIEEILISH | 12 | "All the Good Girls Go to Hell" singer who won the 2019 American Music Award for New Artist of the Year (2 wds.) |
| 43% | JANELLEMONAE | 12 | Actress in the Best Picture winner "Moonlight" who was nominated for an Album of the Year Grammy in 2019: 2 wds. |
| 43% | RICHARDHARRIS | 13 | Actor in the Best Picture winner "Unforgiven" who was nominated for an Album of the Year Grammy in 1968: 2 wds. |
| 42% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 42% | CYNDILAUPER | 11 | "Girls Just Wanna Have Fun" singer who won the Grammy for Best New Artist in 1985: 2 wds. |
| 42% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 42% | NORAH | 5 | With 22-Down, "Come Away with Me" singer who won the 2002 Best New Artist Grammy Award |
| 42% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 41% | NOAHKAHAN | 9 | "Hurt Somebody" rock singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 41% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 41% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 41% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 40% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 40% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 40% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 40% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 40% | 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. |