| 100% | ADELE | 5 | Only performer to twice sweep the Album, Record and Song of the Year Grammys |
| 57% | BRUNOMARS | 9 | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| 57% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 48% | ADELE | 5 | Artist with two Record of the Year and two Album of the Year Grammys |
| 47% | HELLO | 5 | Adele hit that won Grammys for Song and Record of the Year |
| 41% | REHAB | 5 | Amy Winehouse 2008 Grammy Award for Song of the Year and Record of the Year winner |
| 40% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 40% | FLOWERS | 7 | Miley Cyrus song that won Record of the Year at the 2024 Grammys |
| 40% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 40% | HER | 3 | Singer nominated for Album of the Year Grammys in 2019 and 2020 (and whose name spells a pronoun) |
| 39% | HELLO | 5 | Adele song that won Record of the Year and Song of the Year Grammy Awards |
| 39% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 39% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 38% | EILISH | 6 | At 18, the youngest person to sweep the four main Grammy categories (Song, Album, Record, Best New Artist) in a single year |
| 38% | FRANKSINATRA | 12 | Actor in the Best Picture winner "From Here to Eternity" who was nominated for seven Album of the Year Grammys: 2 wds. |
| 38% | STEVIE | 6 | Singer Nicks who is the only woman to be inducted into the Rock and Roll Hall of Fame twice |
| 38% | REHAB | 5 | Song of the Year at the 2008 Grammys |
| 37% | BLACK | 5 | "Man in ___," 1971 song written and recorded by Johnny Cash from album of the same name |
| 37% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 37% | HELLO | 5 | Adele song that won the 2016 Record of the Year and Song of the Year Grammy Awards |
| 37% | RIGHTONTIME | 11 | 2021 song by 32-Across nominated for three Grammy Awards, including Record of the Year and Song of the Year (3 wds.) |
| 37% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 37% | ADELE | 5 | Song of the Year winner for "Hello" at the 2017 Grammys |
| 37% | LONESOME | 8 | "Blue & ___," 25th American studio album by The Rolling Stones and the first one to feature only cover songs |
| 36% | 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. |
| 36% | GRAMMYS | 7 | Record of the Year and Best New Artist |
| 36% | ADELE | 5 | Record of the Year winner at the 2017 Grammys |
| 36% | 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.) |
| 36% | VMAS | 4 | Where Olivia Rodrigo won Best New Artist and Song of the Year in 2021, for short |
| 35% | RAP | 3 | Genre for only two Song of the Year winners in Grammy history |