| 100% | WILLSMITH | 9 | "Ali" actor who received the Generation Award at the 2016 MTV Movie & TV Awards: 2 wds. |
| 52% | JAMIEFOXX | 9 | "Ray" actor who received the 2013 Generation Award: 2 wds. |
| 45% | REBBROWN | 8 | Actor who played the titular character in the TV movie "Captain America" in 1979: 2 wds. |
| 45% | PAULNEWMAN | 10 | "The Sting" star who received the Hersholt Humanitarian Award at the Oscars in 1994: 2 wds. |
| 45% | MICHAELGROSS | 12 | Actor who played Burt Gummer in both the movie and TV series "Tremors": 2 wds. |
| 44% | MORGANFREEMAN | 13 | "Million Dollar Baby" actor who received the SAG Life Achievement Award in 2017: 2 wds. |
| 44% | SANDRABULLOCK | 13 | "The Blind Side" actress who received the 2010 Generation Award: 2 wds. |
| 44% | ANTHONYMACKIE | 13 | "Avengers: Endgame" actor who played Martin Luther King Jr. in the 2016 TV movie "All the Way" (2 wds.) |
| 43% | VIVAVILLA | 9 | 1934 movie for which Wallace Beery won the best actor award at the 2nd Venice Film Festival: 2 wds. |
| 43% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 43% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 42% | SHANIATWAIN | 11 | "That Don't Impress Me Much" singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| 42% | GARYBURGHOFF | 12 | Actor who played "Radar" O'Reilly in both the movie and TV series "M*A*S*H": 2 wds. |
| 42% | PATRICKSWAYZE | 13 | Actor and dancer who rose to fame after doing "Dirty Dancing" and who received formal dance training at the Harkness Ballet, NYC.: 2 wds. |
| 42% | DOLLYPARTON | 11 | Country singer who received the Gary Haber Lifting Lives Award at the 11th Annual ACM Honors: 2 wds. |
| 42% | MILLIONDOLLAR | 13 | "___ Baby," movie directed by Clint Eastwood which received seven Oscar nominations at the 77th Academy Awards: 2 wds. |
| 41% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 41% | MISSYELLIOTT | 12 | "Work It" rapper who received the 2019 MTV Video Vanguard Award, the first female rapper to do so: 2 wds. |
| 41% | JAMESCAGNEY | 11 | "White Heat" star who was the second actor to receive the AFI Life Achievement Award after John Ford: 2 wds. |
| 41% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 41% | CUBAGOODING | 11 | Academy Award-winning actor from "Jerry Maguire", who plays the TV version of 14-Across in "American Crime Story" : 2 wds. |
| 40% | AUSTINMAHONE | 12 | YouTube sensation who was the Artist to Watch at the 2013 MTV Video Music Awards: 2 wds. |
| 40% | BENKINGSLEY | 11 | Actor born in England who won the Academy Award for Best Actor for his portrayal of Mahatma Gandhi in the movie "Gandhi": 2 wds. |
| 40% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 40% | ROGERMOORE | 10 | Actor from the TV series "The Saint", who has played the role of James Bond in seven movies : 2 wds. |
| 40% | EDDIEREDMAYNE | 13 | British actor who received an Academy Award nomination for playing Lili Elbe in "The Danish Girl": 2 wds. |
| 40% | WILLSMITH | 9 | "Ali" actor who won the NAACP Image Award for Entertainer of the Year in 1999: 2 wds. |
| 40% | JEFFREYWRIGHT | 13 | "Westworld" actor who played Martin Luther King Jr. in the 2001 TV movie "Boycott" (2 wds.) |
| 40% | CHRISTIANBALE | 13 | Actor born in Wales who won the Academy Award for Best Supporting Actor for playing Dick Dicky Eklund in the movie "The Fighter": 2 wds |
| 40% | 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. |