| 100% | GARTHBROOKS | 11 | "Friends in Low Places" singer/songwriter honored with the 2020 Gershwin Prize for Popular Song (2 wds.) |
| 70% | STEVIEWONDER | 12 | "Superstition" singer/songwriter honored with the 2009 Gershwin Prize for Popular Song (2 wds.) |
| 68% | SMOKEYROBINSON | 14 | "Being with You" singer/songwriter honored with the 2016 Gershwin Prize for Popular Song (2 wds.) |
| 67% | LIONELRICHIE | 12 | "Say You, Say Me" singer/songwriter honored with the 2022 Gershwin Prize for Popular Song (2 wds.) |
| 64% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 59% | GLORIAESTEFAN | 13 | Miami Sound Machine singer/songwriter honored with her husband Emilio with the 2019 Gershwin Prize for Popular Song (2 wds.) |
| 59% | GARTHBROOKS | 11 | "Friends in Low Places" singer who won the 2020 Gershwin Prize: 2 wds. |
| 45% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 44% | GARTHBROOKS | 11 | "Friends in Low Places" singer with 14 platinum studio albums: 2 wds. |
| 39% | GARTHBROOKS | 11 | "Friends in Low Places" singer who has won the third-most Billboard Music Awards (19) (2 wds.) |
| 37% | JOHNLEGEND | 10 | Singer with the 2020 love song "Bigger Love" (2 wds.) |
| 37% | DEMILOVATO | 10 | Singer with the 2020 love song "I Love Me" (2 wds.) |
| 36% | ANDERSONCOOPER | 14 | CNN host who was honored with the 2018 Walter Cronkite Award for Excellence in Journalism (2 wds.) |
| 36% | JUSTINBIEBER | 12 | Singer with the 2020 love song "That's What Love Is" (2 wds.) |
| 36% | BOBBYRYDELL | 11 | "Volare" singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 35% | ROBINROBERTS | 12 | "Good Morning America" co-anchor who was honored with the 2014 Walter Cronkite Award for Excellence in Journalism (2 wds.) |
| 35% | ELTON | 5 | Singer John honored with a Gershwin Prize in 2024 |
| 34% | TONIMORRISON | 12 | "Beloved" author honored with the National Humanities Medal in 2000: 2 wds. |
| 34% | PHILIPROTH | 10 | "American Pastoral" author honored with the National Humanities Medal in 2010: 2 wds. |
| 34% | RICKTOCCHET | 11 | Vancouver Canucks head coach who was honored with the NHL's Jack Adams Award for coach of the year in 2024 (2 wds.) |
| 34% | CAMILACABELLO | 13 | Pop singer with the hit song "Crying in the Club" (2 wds.) |
| 33% | ELVISCOSTELLO | 13 | "Veronica" new wave singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 33% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 33% | JOHNFOGERTY | 11 | Singer/songwriter whose song 17-Across was honored by the Baseball Hall of Fame in 2010 (2 wds.) |
| 33% | TONESANDI | 9 | Australian singer whose "Dance Monkey" was the #2 song on Spotify in 2020: 3 wds. |
| 33% | ERICCLAPTON | 11 | "I Shot the Sheriff" singer with the 1992 song "Tears in Heaven": 2 wds. |
| 33% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who was honored with the "Billboard" Women in Music Icon Award in 2020 (2 wds.) |
| 33% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 33% | ELTONJOHN | 9 | "Piano man" with the hit song "Candle in the Wind": 2 wds. |
| 32% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |