| 100% | SANDRABULLOCK | 13 | "The Blind Side" actress who received the 2010 Generation Award: 2 wds. |
| 64% | JAMIEFOXX | 9 | "Ray" actor who received the 2013 Generation Award: 2 wds. |
| 60% | CAROLBURNETT | 12 | "The Four Seasons" actress who received the SAG Life Achievement Award in 2015: 2 wds. |
| 59% | SANDRABULLOCK | 13 | Actress who won a Golden Globe, SAG Award, and Oscar for "The Blind Side": 2 wds. |
| 57% | CATHERINEOHARA | 14 | Canadian-born "Schitt's Creek" actress who received the Carnegie Great Immigrants award in 2020: 2 wds. |
| 57% | MIKENICHOLS | 11 | "The Graduate" director who received the AFI Life Achievement Award in 2010: 2 wds. |
| 56% | WILLSMITH | 9 | "Ali" actor who received the Generation Award at the 2016 MTV Movie & TV Awards: 2 wds. |
| 55% | SANDRABULLOCK | 13 | Actress who won an Oscar for Best Actress for "The Blind Side" and a Worst Actress Razzie Award for "All About Steve": 2 wds. |
| 54% | SANDRABULLOCK | 13 | "The Blind Side" actress who played a crossword constructor in 33-Across: 2 wds. |
| 54% | LORENAOCHOA | 11 | 2007 Women's British Open winner who received the Best Female Golfer ESPY Award in 2009 and 2010: 2 wds. |
| 52% | ANGELINAJOLIE | 13 | "Maleficent" star who received the Hersholt Humanitarian Award in 2013: 2 wds. |
| 52% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 52% | LIZAMINNELLI | 12 | "Cabaret" star who received the GLAAD Vanguard Award in 2005: 2 wds. |
| 52% | JERRYLEWIS | 10 | "The Nutty Professor" star who received the Hersholt Humanitarian Award in 2009: 2 wds. |
| 51% | NEILDIAMOND | 11 | "Sweet Caroline" singer who received the Billboard Icon Award in 2011: 2 wds. |
| 51% | JANETJACKSON | 12 | "Rhythm Nation" singer who received the GLAAD Vanguard Award in 2008: 2 wds. |
| 51% | JENNIFERLOPEZ | 13 | "Waiting for Tonight" singer who received the Billboard Icon Award in 2014: 2 wds. |
| 50% | DANNYGLOVER | 11 | "Lethal Weapon" star who received the Hersholt Award in 2022: 2 wds. |
| 50% | AMANDASEALES | 12 | "Insecure" actress who hosted the socially distant 2020 BET Awards: 2 wds. |
| 50% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who received the GLAAD Vanguard Award in 2009: 2 wds. |
| 50% | PAULNEWMAN | 10 | "The Sting" star who received the Hersholt Humanitarian Award at the Oscars in 1994: 2 wds. |
| 49% | SANDRABULLOCK | 13 | Best Actress Oscar winner for "The Blind Side" who was a Worst Actress Razzie winner for "All About Steve": 2 wds. |
| 49% | SELENAGOMEZ | 11 | "Only Murders in the Building" actress who received a kidney transplant in 2017: 2 wds. |
| 49% | SANDRABULLOCK | 13 | Actress who plays a mother in "The Blind Side" (2 wds.) |
| 49% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 49% | ROBINROBERTS | 12 | "Good Morning America" coanchor who received the 2013 Arthur Ashe Courage Award: 2 wds. |
| 49% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 49% | GEORGELUCAS | 11 | "Star Wars" director who received the AFI Life Achievement Award in 2005: 2 wds. |
| 49% | MARTINSCORSESE | 14 | "Raging Bull" director who received the AFI Life Achievement Award in 1997: 2 wds. |
| 49% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |