| 100% | JIMIHENDRIX | 11 | Legendary guitarist who performed "The Star-Spangled Banner" at Woodstock 50 years ago: 2 wds. |
| 57% | JANISJOPLIN | 11 | Rock/blues singer who performed "To Love Somebody" at Woodstock 50 years ago: 2 wds. |
| 44% | THEBAND | 7 | One-time backup for Bob Dylan that performed "Chest Fever" at Woodstock 50 years ago: 2 wds. |
| 40% | MARIAHCAREY | 11 | Pop star who performed and cowrote the song at 19-/33-Across: 2 wds. |
| 37% | KERRISTRUG | 10 | American retired gymnast who performed the vault despite injuring her ankle at the 1996 Olympics: 2 wds. |
| 37% | JIMMYKIMMEL | 11 | ABC talk show host who performed at the 2012 White House Correspondents' Dinner: 2 wds. |
| 37% | CONANOBRIEN | 11 | TBS talk show host who performed at the 2013 White House Correspondents' Dinner: 2 wds. |
| 37% | JIMMYKIMMEL | 11 | ABC host who performed at the 2012 White House Correspondents' Dinner: 2 wds. |
| 37% | MICHELLEWOLF | 12 | Netflix host who performed at the 2018 White House Correspondents' Dinner: 2 wds. |
| 37% | CONANOBRIEN | 11 | TBS host who performed at the 2013 White House Correspondents' Dinner: 2 wds. |
| 36% | GAYE | 4 | Singer Marvin who performed a memorable version of "The Star-Spangled Banner" at the 1983 NBA All-Star Game |
| 35% | PAULSIMON | 9 | Singer who performed "Still Crazy After All These Years" on the SNL40 anniversary special: 2 wds. |
| 35% | MICHELLEWOLF | 12 | Former Netflix variety show host who performed at the 2018 White House Correspondents' Dinner: 2 wds. |
| 34% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 33% | FAYEDUNAWAY | 11 | She was Bonnie in "Bonnie and Clyde," which was released 50 years ago: 2 wds. |
| 33% | SANTANA | 7 | Mexican-American rock group that performed "Evil Ways" at Woodstock 50 years ago |
| 33% | ANDRADAY | 8 | Singer who performed "Stand Up for Something" at the 2018 Oscars, accompanied by Common and various activists: 2 wds. |
| 32% | HENDRIX | 7 | Guitarist who famously played the national anthem at Woodstock |
| 32% | SHERYLCROW | 10 | "All I Wanna Do" singer who performed the theme to "Tomorrow Never Dies": 2 wds. |
| 32% | WANDASYKES | 10 | "The Upshaws" star who performed stand-up in the 2019 Netflix comedy special subtitled "Not Normal": 2 wds. |
| 31% | FIONAAPPLE | 10 | Grammy-winning singer who performs the theme song "Container" on "The Affair": 2 wds. |
| 31% | BERT | 4 | ___ Sommer, "America" singer who performed at the 1969 Woodstock Festival |
| 31% | SANTANA | 7 | "Evil Ways" band who performed at the 1969 Woodstock Festival |
| 31% | TONYHAWK | 8 | Legendary skateboarder who completed the first recorded 900: 2 wds. |
| 31% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 31% | MOMSMABLEY | 10 | Trailblazing African American who was the first female comedian to perform at the Apollo Theater: 2 wds. |
| 31% | RAVI | 4 | ___ Shankar, Indian sitar player who performed at the 1969 Woodstock Festival |
| 31% | ONEEYEDWILLY | 12 | Legendary pirate who hid the treasure in "The Goonies": 2 wds. |
| 31% | PAULNEWMAN | 10 | "The Sting" star who received the Hersholt Humanitarian Award at the Oscars in 1994: 2 wds. |
| 31% | NOVAKDJOKOVIC | 13 | Serbian tennis star who won the Men's Singles at the 2018 Wimbledon Championships: 2 wds. |