| 100% | SAMSMITH | 8 | "Stay With Me" singer who won 14-Across in 2015: 2 wds. |
| 66% | FETTYWAP | 8 | "Trap Queen" singer who won 14-Across in 2016: 2 wds. |
| 60% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 56% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 54% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 53% | 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. |
| 52% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 52% | SAM | 3 | ___ Smith, "Stay With Me" singer who was 22 when they won the 2015 Grammy for Record of the Year |
| 52% | LORDE | 5 | "Royals" singer who won 14-Across in 2014 |
| 51% | 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. |
| 51% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 50% | ONEDIRECTION | 12 | "Drag Me Down" group that won 14-Across in 2013: 2 wds. |
| 49% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 49% | NATALIECOLE | 11 | "Unforgettable" singer who won the Best New Artist Grammy in 1976: 2 wds. |
| 49% | PAULMCCARTNEY | 13 | Singer who came up with "Yesterday" in his sleep: 2 wds. |
| 49% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 49% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 49% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 49% | OLIVIARODRIGO | 13 | "Drivers License" singer who won a Best New Artist Grammy in 2022: 2 wds. |
| 48% | SAMSMITH | 8 | "Stay With Me" singer/songwriter: 2 wds. |
| 48% | MARIAHCAREY | 11 | "Vision of Love" singer who won the Best New Artist Grammy in 1991: 2 wds. |
| 48% | TRACYCHAPMAN | 12 | "Fast Car" singer who won the Grammy for Best New Artist in 1989: 2 wds. |
| 48% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 48% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 48% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who won the Best New Artist Grammy in 1974: 2 wds. |
| 48% | CARLYSIMON | 10 | "You're So Vain" singer who won the Best New Artist Grammy in 1972: 2 wds. |
| 48% | TONIBRAXTON | 11 | "Another Sad Love Song" singer who won the Best New Artist Grammy in 1994: 2 wds. |
| 48% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 48% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 48% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |