| 100% | JAMIEFOXX | 9 | "Ray" actor who received the 2013 Generation Award: 2 wds. |
| 72% | WILLSMITH | 9 | "Ali" actor who received the Generation Award at the 2016 MTV Movie & TV Awards: 2 wds. |
| 64% | ROBINROBERTS | 12 | "Good Morning America" coanchor who received the 2013 Arthur Ashe Courage Award: 2 wds. |
| 63% | MORGANFREEMAN | 13 | "Million Dollar Baby" actor who received the SAG Life Achievement Award in 2017: 2 wds. |
| 63% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 63% | SANDRABULLOCK | 13 | "The Blind Side" actress who received the 2010 Generation Award: 2 wds. |
| 60% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 59% | ANGELINAJOLIE | 13 | "Maleficent" star who received the Hersholt Humanitarian Award in 2013: 2 wds. |
| 55% | EDDIEREDMAYNE | 13 | British actor who received an Academy Award nomination for playing Lili Elbe in "The Danish Girl": 2 wds. |
| 55% | KIRKDOUGLAS | 11 | "Spartacus" actor who received the French Legion of Honor medal in 1985: 2 wds. |
| 54% | DANNYGLOVER | 11 | "Lethal Weapon" star who received the Hersholt Award in 2022: 2 wds. |
| 53% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 53% | GEORGELUCAS | 11 | "Star Wars" director who received the AFI Life Achievement Award in 2005: 2 wds. |
| 53% | MARTINSCORSESE | 14 | "Raging Bull" director who received the AFI Life Achievement Award in 1997: 2 wds. |
| 53% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 53% | JESSYENORMAN | 12 | Opera star with five Grammys who received the Spingarn Medal in 2013: 2 wds. |
| 53% | KEVINSPACEY | 11 | Actor who's hosting the 71st Tony Awards June 11: 2 wds. |
| 52% | CAITLYNJENNER | 13 | Transgender track-and-field star who received the 2015 Arthur Ashe Courage Award: 2 wds. |
| 52% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 52% | ERNIEBANKS | 10 | Cubs Hall of Famer who received the Presidential Medal of Freedom in 2013: 2 wds. |
| 52% | ANANAVARRO | 10 | Nicaraguan-born CNN political commentator who received the Carnegie Great Immigrants award in 2020: 2 wds. |
| 52% | DAVIDBYRNE | 10 | Scottish-born Talking Heads musician who received the Carnegie Great Immigrants award in 2020: 2 wds. |
| 52% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 52% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 52% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 52% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 51% | CATHERINEOHARA | 14 | Canadian-born "Schitt's Creek" actress who received the Carnegie Great Immigrants award in 2020: 2 wds. |
| 51% | CARLOSSANTANA | 13 | "Oye Como Va" musician who received the Billboard Latin Music Lifetime Achievement Award in 2009: 2 wds. |
| 51% | EMILIOESTEFAN | 13 | Miami Sound Machine musician who received the Billboard Latin Music Lifetime Achievement Award in 1994: 2 wds. |
| 51% | MIKENICHOLS | 11 | "The Graduate" director who received the AFI Life Achievement Award in 2010: 2 wds. |