| 100% | JANETJACKSON | 12 | "Rhythm Nation" singer who received the GLAAD Vanguard Award in 2008: 2 wds. |
| 69% | LIZAMINNELLI | 12 | "Cabaret" star who received the GLAAD Vanguard Award in 2005: 2 wds. |
| 61% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who received the GLAAD Vanguard Award in 2009: 2 wds. |
| 59% | JANETJACKSON | 12 | "Rhythm Nation" R&B singer who received the 1990 MTV Video Vanguard Award, the first African American woman to do so: 2 wds. |
| 58% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 58% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 57% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 57% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 56% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 56% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 56% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 56% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 56% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 56% | JENNIFERLOPEZ | 13 | "Waiting for Tonight" singer who received the Billboard Icon Award in 2014: 2 wds. |
| 55% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 55% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 55% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who received the Willie Nelson Lifetime Achievement Award in 2020: 2 wds. |
| 55% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 54% | CYNDILAUPER | 11 | "Girls Just Want to Have Fun" singer who received the Billboard Women in Music Icon Award in 2018: 2 wds. |
| 54% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 54% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 53% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 53% | SMOKEYROBINSON | 14 | "The Tears of a Clown" singer who received the BET Lifetime Achievement Award in 2015: 2 wds. |
| 52% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 52% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 51% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 51% | HARRYBELAFONTE | 14 | "Day-O" singer who received the Spingarn Medal in 2012: 2 wds. |
| 49% | MARYJBLIGE | 10 | "Not Gon' Cry" singer who received the BET Lifetime Achievement Award in 2019: 3 wds. |
| 49% | ANGELINAJOLIE | 13 | "Maleficent" star who received the Hersholt Humanitarian Award in 2013: 2 wds. |
| 48% | DOLLYPARTON | 11 | Country singer who received the Gary Haber Lifting Lives Award at the 11th Annual ACM Honors: 2 wds. |