| 100% | RAITT | 5 | She won three Grammys for her 1989 album "Nick of Time" |
| 56% | RAITT | 5 | Her "Nick of Time" won the Grammy for Album of the Year |
| 53% | GRAMMYAWARD | 11 | Prize that 17-Across won three times for her spoken-word albums: 2 wds. |
| 49% | ALICIA | 6 | Keys who won five Grammys for her debut album |
| 48% | RAITT | 5 | 1989 Album of the Year Grammy winner, for “Nick of Time” |
| 47% | ANGELOU | 7 | Poet who won three Grammys for Best Spoken Word Album |
| 42% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 42% | RAITT | 5 | 1989 Grammy winner for "Nick of Time" |
| 41% | RAITT | 5 | Singer with the 5x platinum album "Nick of Time," 1989 |
| 41% | LORDE | 5 | She won two Grammys for "Royals" |
| 40% | ANNEHATHAWAY | 12 | "Les Misérables" actress who won an Oscar for her performance, despite only 15 minutes of screen time: 2 wds. |
| 40% | ROOMS | 5 | "___ on Fire," 1989 Stevie Nicks track from her album "The Other Side of the Mirror" |
| 40% | MARENMORRIS | 11 | Her "Girl" won the 2019 CMA for Album of the Year: 2 wds. |
| 39% | MARYMARTIN | 10 | She won three Tony Awards for Best Actress in a Musical, for "South Pacific," "Peter Pan," and "The Sound of Music": 2 wds. |
| 39% | ALLISONJANNEY | 13 | "I, Tonya" actress who won an Oscar for her performance, despite only 15 minutes and 37 seconds of screen time: 2 wds. |
| 38% | PENELOPECRUZ | 12 | "Vicky Cristina Barcelona" actress who won an Oscar for her performance, despite only 14 minutes and 29 seconds of screen time: 2 wds. |
| 37% | JARS | 4 | ___ of Clay (Christian band that's won three Grammys) |
| 37% | ASIAM | 5 | 2007 Alicia Keys album that won three Grammys |
| 37% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 35% | PIAF | 4 | Cotillard won Best Actress for playing her |
| 35% | KESHA | 5 | One-named singer nominated for two Grammys for her 2017 "Rainbow" album |
| 35% | QUEENANNE | 9 | Olivia Colman won an Oscar for playing her |
| 34% | ADELE | 5 | She won Album of the Year honors in 2012 and 2017 |
| 34% | UMA | 3 | Thurman with a species of lizards named for her |
| 34% | PATINA | 6 | Miller who won a Tony for her performance in the 2013 revival of “Pippin” |
| 34% | EDGAR | 5 | Award for Best Novel won three times by Dick Francis |
| 34% | NOONE | 5 | Who has won an Oscar for Best Actor three times |
| 34% | SUZANNEVEGA | 11 | 1990 Grammy winner for her album "Days of Open Hand" |
| 34% | BARENAKED | 9 | __ Ladies; won 2001 Juno for Pop Album of the Year |
| 34% | HEART | 5 | "Elastic ___," hit song written and performed by Sia for her album "1000 Forms of Fear" |