So recently I read that Troy Gentile from The Goldbergs played a young version of Jack Black’s character in Nacho Libre, and then played a young Jack Black in Tenacious D The Pick of Destiny.
Have any other actors played a younger version of another actor in more than one movie?
Obvious references are James McAvoy as young Patrick Stewart, Michael Fassbender as a young Sir Ian McKellan, and Jennifer Lawrence as a young Rebecca Romijn in the recent X-Men movies.
ETA: The recent ones being X-Men: First Class and Days of Future Past.
This should at least get honorable mention: In 1971’s Sweet Sweetback’s Baadasssss Song, Mario van Peebles portrayed the young version of Sweet Sweetback, who was played by his father Melvin van Peebles. Thirty years later, in the biographical film Baadasssss!, Mario portrayed the role of his father, as well as the role of Sweetback in the film he was trying to produce and distribute. So essentially, Mario van Peebles has played a younger version of himself.
The differences in stature and general appearance are intentional, as the older doctor views his younger self as a small, stupid kid, who had no idea what he was getting into.
Isis Carmen Jones is an actress with two IMDB credits. One is for playing the young Delores in Sister Act, in which the older Delores is played by Whoopi Goldberg.
The other is for playing a young Guinan in ST-TNG, in which the elder Guinan is played by Whoopi Goldberg.
Robert De Niro played a younger version of Vito Corleone in The Godfather II, the role that Marlon Brando played in the original Godfather. Both actors won Academy Awards for their respective films, too, Brando for Best Actor and De Niro for Best Supporting Actor.
This seems to be the only post that fits what I assume the OP wanted. The others are all just younger versions of specific characters–some of them, for some reason, not even in more than one movie.
So, it’s asking about actors who have played a real-life person (who also happens to be an actor, or at least an entertainer of some kind) in more than one film?
Larry Parks portrayed Al Jolson twice, in The Jolson Story and Jolson Sings Again.
Michael Sheen has portrayed Tony Blair several times, for sufficiently generous definitions of “entertainer.”
Er, Ronald Reagan was an actor, and both Richard Crenna and Josh Brolin played him; Brolin played a younger Reagan although Crenna didn’t, albeit that Crenna was playing a version of Reagan younger than the real-life Reagan (who was still alive at the time).