I do need to add Nick Fury to this quiz, though. With his appearance in Captain America: The Winter Soldier he's up to 7 big screen appearances played by the same actor, and he was even on the Agents of SHIELD TV series, though that doesn't count for the purposes of this quiz.
Maybe make one with just the leading role? And then you can drop it down to 5 apearances. (cause 6 of the roles, and 15 of these actors I have never heard about. Not that my knowlegde should be the standard. But I mean, people tend to remember the leading roles the best)
brief note: while doing research for the update, I came across the fact that on IMDB there are seven film appearances each listed for both Jay and Silent Bob (played by Jason Mewes and Kevin Smith). However, one of those seven films is something called Lucy You Love It. I can't find any information about this film at all, except that it was apparently released in 2000 and in at least one place it's listed as a documentary. Other than that, nothing. So I'm going to assume that it did not have a wide theatrical release and is therefore not counted for this quiz.
Chasing Amy (1997)
Scream 3 (2000)
Jay and Silent Bob Strike Back (2001)
Clerks II (2006)
Clerks III (2016)
X-Men, X-Men 2, X-Men the Last Stand, X-Men Origins: Wolverine, The Wolverine, X-Men: Days of Future Past, and Logan