| 100% | EVAPERON | 8 | Leader portrayed by Patti LuPone and Madonna (2 wds.) |
| 81% | EVAPERON | 8 | Argentine leader played by Patti LuPone and Madonna (2 wds.) |
| 50% | NORMADESMOND | 12 | Character portrayed by actress Patti LuPone in the musical "Sunset Boulevard" which was based on a 1950 film of the same title: 2 wds. |
| 46% | VANGOGH | 7 | Dutch artist portrayed by 15-Across, 20-Across, and 34-Across: 2 wds. |
| 46% | JAMESBOND | 9 | Fictional spy portrayed by actors such as Daniel Craig and Pierce Brosnan: 2 wds. |
| 45% | EVITA | 5 | Role for Patti LuPone and Madonna |
| 44% | LEOPOLDBLOOM | 12 | Partner of 31-Across portrayed by Gene Wilder in 1967 and Matthew Broderick in 2005: 2 wds. |
| 44% | SHERLOCKHOLMES | 14 | Detective portrayed by Robert Downey Jr., who is known for his unmatched observation and deductive skills: 2 wds. |
| 43% | MAXBIALYSTOCK | 13 | Shady Broadway dealmaker in 14-Across portrayed by Zero Mostel in 1967 and Nathan Lane in 2005: 2 wds. |
| 41% | EVITA | 5 | Argentine icon played by Madonna and Patti LuPone |
| 40% | GREGHEFFLEY | 11 | Boy cartoonist portrayed by Zachary Gordon and Jason Drucker in the "Diary of a Wimpy Kid" movies: 2 wds. |
| 39% | ARTIEABRAMS | 11 | Guitarist portrayed by Kevin McHale on "Glee": 2 wds. |
| 38% | FINNHUDSON | 10 | "Glee" character who was portrayed by 29-Across: 2 wds. |
| 38% | JAMESBRADDOCK | 13 | Boxer portrayed by Russell Crowe in "Cinderella Man": 2 wds. |
| 38% | RUBINCARTER | 11 | Boxer portrayed by Denzel Washington in "The Hurricane": 2 wds. |
| 38% | ALIG | 4 | Obtuse journalist portrayed by Sacha Baron Cohen: 2 wds. |
| 38% | ALIG | 4 | Rapper portrayed by Sacha Baron Cohen: 2 wds. |
| 38% | JAKELAMOTTA | 11 | Boxer portrayed by Robert De Niro in "Raging Bull": 2 wds. |
| 38% | SELINAMEYER | 11 | Fictional president portrayed by Julia Louis-Dreyfus on "Veep": 2 wds. |
| 38% | BILLCLINTON | 11 | President portrayed by Darrell Hammond on "Saturday Night Live": 2 wds. |
| 38% | HARRYPOTTER | 11 | Boy wizard portrayed by Daniel Radcliffe in eight movies: 2 wds. |
| 37% | TRAPPERJOHN | 11 | Physician portrayed by Wayne Rogers on "M*A*S*H": 2 wds. |
| 37% | SAYIDJARRAH | 11 | A former Iraqi soldier in "Lost," portrayed by Naveen Andrews: 2 wds. |
| 37% | JOSIAHBARTLET | 13 | Fictional president portrayed by Martin Sheen on "The West Wing": 2 wds. |
| 37% | MARCUSWELBY | 11 | Physician portrayed by Robert Young on a 1960s-1970s TV series: 2 wds. |
| 37% | TYCOBB | 6 | Baseball great portrayed by Tommy Lee Jones in a 1994 film: 2 wds. |
| 37% | RICHARDCROSBY | 13 | Character portrayed by actor Gary Oldman in the hit sitcom "Friends": 2 wds. |
| 37% | JEFFREYWIGAND | 13 | Big Tobacco whistleblower portrayed by Russell Crowe in a 1999 movie: 2 wds. |
| 37% | KARENSILKWOOD | 13 | Nuclear plant whistleblower portrayed by Meryl Streep in a 1983 movie: 2 wds. |
| 37% | FREDDYKRUEGER | 13 | Antagonist of "A Nightmare on Elm Street" portrayed by Robert Englund: 2 wds. |