| 100% | GLORIAESTEFAN | 13 | Miami Sound Machine singer/songwriter honored with her husband Emilio with the 2019 Gershwin Prize for Popular Song (2 wds.) |
| 53% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who, with her husband Emilio, won the 2019 Gershwin Prize: 2 wds. |
| 51% | STEVIEWONDER | 12 | "Superstition" singer/songwriter honored with the 2009 Gershwin Prize for Popular Song (2 wds.) |
| 50% | SMOKEYROBINSON | 14 | "Being with You" singer/songwriter honored with the 2016 Gershwin Prize for Popular Song (2 wds.) |
| 50% | GARTHBROOKS | 11 | "Friends in Low Places" singer/songwriter honored with the 2020 Gershwin Prize for Popular Song (2 wds.) |
| 50% | LIONELRICHIE | 12 | "Say You, Say Me" singer/songwriter honored with the 2022 Gershwin Prize for Popular Song (2 wds.) |
| 45% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 43% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 34% | TRISHAYEARWOOD | 14 | Country singer who, along with her husband, helps build houses for Habitat for Humanity: 2 wds. |
| 33% | JENNIFERLOPEZ | 13 | Singer famous for her hit song "On the Floor" with Pitbull, who also starred as the lead role in the film "Maid in Manhattan": 2 wds. |
| 32% | DAVECHAPPELLE | 13 | Former "Saturday Night Live" comedian honored with the 2019 Mark Twain Prize for American Humor (2 wds.) |
| 31% | GLORIAESTEFAN | 13 | Miami Sound Machine singer who is a 2023 Songwriters Hall of Fame inductee (2 wds.) |
| 31% | STEVIEWONDER | 12 | American singer with 25 Grammy Awards famous for his song "You Are the Sunshine of My Life": 2 wds. |
| 30% | NIPSEYHUSSLE | 12 | Musician/activist honored posthumously with the 2019 BET Award for Best Male Hip Hop Artist (2 wds.) |
| 30% | YOLANDAADAMS | 12 | "Be Blessed" gospel singer who was honored with the 2019 Soul Train Lady of Soul Award: 2 wds. |
| 30% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 29% | GLORIAESTEFAN | 13 | Songwriters Hall of Famer and Miami Sound Machine lead singer who was born September 1, 1957 (2 wds.) |
| 29% | ALEXMORGAN | 10 | Soccer great honored with the 2019 ESPY Award for Best Female 34-Down (2 wds.) |
| 29% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |
| 29% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 29% | BILLWITHERS | 11 | Singer with the 1971 song "Ain't No Sunshine": 2 wds. |
| 29% | TAYLORSWIFT | 11 | "Anti-Hero" singer who was honored with the People's Choice Award for The Female Artist of 2022 (2 wds.) |
| 28% | BREANNASTEWART | 14 | Basketball great honored with the 2019 ESPY Award for Best WNBA Player (2 wds.) |
| 28% | SPACECOWBOY | 11 | Kacey Musgraves single that won the 2019 Grammy for Best Country Song: 2 wds. |
| 28% | 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. |
| 28% | HARRYSTYLES | 11 | "As It Was" singer who was honored with the People's Choice Award for The Male Artist of 2022 (2 wds.) |
| 28% | VANMORRISON | 11 | Rock singer with the 1971 song "Wild Night": 2 wds. |
| 28% | BIGMISTAKE | 10 | Song by Australian singer-songwriter Natalie Imbruglia from her debut album "Left of the Middle": 2 wds. |
| 28% | STEPHENCURRY | 12 | NBA star honored with the 2019 BET Award for Sportsman of the Year (2 wds.) |
| 28% | SERENAWILLIAMS | 14 | Tennis great honored with the 2019 ESPY Award for Best Female Tennis Player (2 wds.) |