| 100% | COLINFARRELL | 12 | He played bad boss Bobby Pellitt in "Horrible Bosses": 2 wds. |
| 67% | DAVIDSPADE | 10 | He played bad boss Russell Dunbar in "Rules of Engagement": 2 wds. |
| 53% | GLENNCLOSE | 10 | She played bad boss Cruella de Vil in "101 Dalmatians": 2 wds. |
| 51% | JACKPALANCE | 11 | He won an Oscar playing trail boss Curly Washburn in the 1991 comedy "City Slickers": 2 wds. |
| 51% | DICKTRACY | 9 | 1990 Al Pacino movie in which he plays crime boss Alphonse "Big Boy" Caprice: 2 wds. |
| 48% | JASONBATEMAN | 12 | "Horrible Bosses 2" actor who plays Max in "Game Night": 2 wds. |
| 48% | BILLYCRYSTAL | 12 | He played account executive Mitch Robbins in "City Slickers": 2 wds. |
| 47% | JUDDNELSON | 10 | He played "the criminal" John in "The Breakfast Club": 2 wds. |
| 47% | MRT | 3 | He played Clubber Lang in "Rocky III": 2 wds. |
| 47% | ALPACINO | 8 | He played Michael Corleone in "The Godfather": 2 wds. |
| 47% | CLEAVONLITTLE | 13 | He played Sheriff Bart in "Blazing Saddles": 2 wds. |
| 47% | JEREMYPIVEN | 11 | He played agent Ari Gold in "Entourage": 2 wds. |
| 47% | MICHAELKEATON | 13 | He played Batman in 1989's "Batman": 2 wds. |
| 46% | MATTDAMON | 9 | He plays Max De Costa in "Elysium": 2 wds. |
| 46% | CHARLIEDAY | 10 | "Horrible Bosses 2" actor who plays Dr. Newt Geiszler in "Pacific Rim Uprising": 2 wds. |
| 46% | ALECBALDWIN | 11 | He played Adam Maitland's ghost in "Beetlejuice": 2 wds. |
| 46% | ROBERTSHAW | 10 | "Jaws" actor who played crime boss Doyle Lonnegan in "The Sting": 2 wds. |
| 46% | EDWARDFURLONG | 13 | He played John Connor in "Terminator 2: Judgment Day": 2 wds. |
| 46% | ELIJAHWOOD | 10 | He played Frodo in "The Lord of the Rings": 2 wds. |
| 46% | MORGANFREEMAN | 13 | He played Nelson Mandela in the 2009 movie "Invictus": 2 wds. |
| 46% | KELSEYGRAMMER | 13 | He played Frasier Crane in a "Cheers" spin-off: 2 wds. |
| 46% | CHRISTIANBALE | 13 | He played Batman in the 2005 movie "Batman Begins": 2 wds. |
| 46% | GEORGECLOONEY | 13 | He played Batman in the 1997 movie "Batman & Robin": 2 wds. |
| 46% | ADRIANGRENIER | 13 | He played big-name actor Vincent Chase in "Entourage": 2 wds. |
| 46% | HENRYTHOMAS | 11 | He played Elliott in "E.T. the Extra-Terrestrial": 2 wds. |
| 46% | MATTHEWPERRY | 12 | He plays sloppy Oscar Madison in 31-/33-Across: 2 wds. |
| 46% | THOMASLENNON | 12 | He plays tidy Felix Unger in 31-/33-Across: 2 wds. |
| 45% | MICHAELKEATON | 13 | He played Betelgeuse in "Beetlejuice": 2 wds. |
| 45% | JOHNCANDY | 9 | He played Barf in "Spaceballs": 2 wds. |
| 45% | COREYFELDMAN | 12 | He played talkative kid "Mouth" in "The Goonies": 2 wds. |