| 100% | LIZAMINNELLI | 12 | "Cabaret" star who received the GLAAD Vanguard Award in 2005: 2 wds. |
| 74% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who received the GLAAD Vanguard Award in 2009: 2 wds. |
| 73% | JANETJACKSON | 12 | "Rhythm Nation" singer who received the GLAAD Vanguard Award in 2008: 2 wds. |
| 63% | ANGELINAJOLIE | 13 | "Maleficent" star who received the Hersholt Humanitarian Award in 2013: 2 wds. |
| 62% | DANNYGLOVER | 11 | "Lethal Weapon" star who received the Hersholt Award in 2022: 2 wds. |
| 60% | GEORGELUCAS | 11 | "Star Wars" director who received the AFI Life Achievement Award in 2005: 2 wds. |
| 60% | JERRYLEWIS | 10 | "The Nutty Professor" star who received the Hersholt Humanitarian Award in 2009: 2 wds. |
| 56% | PAULNEWMAN | 10 | "The Sting" star who received the Hersholt Humanitarian Award at the Oscars in 1994: 2 wds. |
| 53% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 52% | CAITLYNJENNER | 13 | Transgender track-and-field star who received the 2015 Arthur Ashe Courage Award: 2 wds. |
| 50% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 49% | JENNIFERLOPEZ | 13 | "Waiting for Tonight" singer who received the Billboard Icon Award in 2014: 2 wds. |
| 49% | MISSYELLIOTT | 12 | "Work It" rapper who received the 2019 MTV Video Vanguard Award, the first female rapper to do so: 2 wds. |
| 48% | LORENAOCHOA | 11 | 2007 Women's British Open winner who received the Best Female Golfer ESPY Award in 2009 and 2010: 2 wds. |
| 48% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 47% | 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. |
| 47% | MIKENICHOLS | 11 | "The Graduate" director who received the AFI Life Achievement Award in 2010: 2 wds. |
| 47% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 47% | MARTINSCORSESE | 14 | "Raging Bull" director who received the AFI Life Achievement Award in 1997: 2 wds. |
| 47% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 47% | JAMIEFOXX | 9 | "Django Unchained" star who hosted the ESPY Awards in 2003 and 2004: 2 wds. |
| 46% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 46% | CAROLBURNETT | 12 | "The Four Seasons" actress who received the SAG Life Achievement Award in 2015: 2 wds. |
| 46% | TYLER | 5 | With 34-Across, "Madea" star who received the Hersholt Award in 2021 |
| 46% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 46% | MORGANFREEMAN | 13 | "Million Dollar Baby" actor who received the SAG Life Achievement Award in 2017: 2 wds. |
| 46% | MARTINSCORSESE | 14 | "Raging Bull" director who received the French Legion of Honor medal in 2005: 2 wds. |
| 46% | FRANKROBINSON | 13 | Orioles Hall of Famer who received the Presidential Medal of Freedom in 2005: 2 wds. |
| 46% | TINAFEY | 7 | "30 Rock" star who was awarded the Mark Twain Prize in 2010: 2 wds. |
| 46% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |