| STEVIEWONDER | Superstition singer who has won 25 Grammys: 2 wds. |
| KLAMMER | Franz , Austrian ski racer who won 25 World Cup downhill races (7) |
| JOELOUIS | U.S. boxer, world heavyweight champion who won 25 consecutive title defences from 1937-49 (3,5) |
| ALISONKRAUSS | When You Say Nothing at All country singer who has won 27 Grammys: 2 wds. |
| JONIMITCHELL | "Help Me" singer/songwriter who has nine Grammys: 2 wds. |
| VICTORIAMONET | On My Mama R&B singer who won Best New Artist at the 2024 Grammys: 2 wds. |
| NOAHKAHAN | Hurt Somebody rock singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| JELLYROLL | Need a Favor country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| FRANKSINATRA | Actor in the Best Picture winner From Here to Eternity who was nominated for seven Album of the Year Grammys: 2 wds. |
| ELTONJOHN | Pop star who sang a duet with Lady Gaga on his hit Your Song at the 2010 Grammys: 2 wds. |
| TONYBENNETT | Crooner who sang a duet with Lady Gaga on the standard Cheek to Cheek at the 2015 Grammys: 2 wds. |
| NILERODGERS | Producer who played guitar while Lady Gaga sang a David Bowie medley at the 2016 Grammys: 2 wds. |
| THEBOX | 2020 Roddy Ricch chart-topper nominated for three Grammys: 2 wds. |
| SMALLWONDER | "Superstition" singer Stevie, as a child? |
| ADELE | British singer who has won 15 Grammys since 2009 |
| ENYA | Irish singer who has won four Grammys |
| BRUNOMARS | Winner of Album, Record, and Song of the Year at the 2018 Grammys: 2 wds. |
| STEVIE | "Superstition" singer Wonder |
| BETTEMIDLER | Actress and singer who has won three Grammys, four Golden Globes, three Emmys and two Tony Award (5,6) |
| BENNETT | Tony___ (b 1926), US singer who has won 19 Grammy Awards (7) |
