| 100% | BRYSONTILLER | 12 | "Don't" singer who was Billboard's Top New Artist of 2016: 2 wds. |
| 78% | JUSTINBIEBER | 12 | "Love Yourself" pop singer who was Billboard's Top Male Artist of 2016: 2 wds. |
| 61% | ADELE | 5 | "Hello" singer who was Billboard's Top Artist and Top Female Artist of 2016 |
| 55% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 54% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 54% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 52% | DRAKE | 5 | "Hotline Bling" rapper who was Billboard's Top Hot 100 Artist of 2016 |
| 51% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 49% | EARTHAKITT | 10 | "Santa Baby" singer who was the voice of villainous Yzma in Disney's "The Emperor's New Groove": 2 wds. |
| 48% | DOJACAT | 7 | 13-Across, 19-Across, and 38-Across singer who was named New Artist of the Year at the 2020 American Music Awards (2 wds.) |
| 47% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 47% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer who was named Billboard's 2018 Woman of the Year (2 wds.) |
| 46% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 45% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 45% | CAMILACABELLO | 13 | "Havana" singer who simultaneously topped the Billboard 200, Hot 100, and Artist 100 in 2018: 2 wds. |
| 45% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 45% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 44% | NOAHKAHAN | 9 | "Hurt Somebody" rock singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 44% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 44% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 43% | BILLIEEILISH | 12 | "Bad Guy" singer who was one of PETA's Most Beautiful Vegan Celebrities in 2021: 2 wds. |
| 43% | ANDERSONPAAK | 12 | Silk Sonic singer who was one of PETA's Most Beautiful Vegan Celebrities in 2021: 2 wds. |
| 43% | LENNYKRAVITZ | 12 | "Fly Away" singer who was one of PETA's Most Beautiful Vegan Celebrities in 2021: 2 wds. |
| 43% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 43% | ADELE | 5 | "Skyfall" singer who has been named Billboard's Artist of the Year thrice |
| 43% | TIKTOK | 6 | Kesha song that was Billboard's top pop song of 2010: 2 wds. |
| 43% | AMYWINEHOUSE | 12 | "Rehab" singer who was one of Tony Bennett's duet partners on his "Duets II" album: 2 wds. |
| 43% | BRETTELDREDGE | 13 | "Lose My Mind" singer who won the 2014 CMA New Artist of the Year award: 2 wds. |
| 43% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 43% | PATTILABELLE | 12 | "New Attitude" singer who was the Flower on season 2 of "The Masked Singer": 2 wds. |