Ok, this is obviously not a film but I’m lumping it on this list anyway.
One of his earliest high-profile professional gigs, a job which he got primarily because Lorne Michaels really wanted Anthony Michael Hall as a regular, and Anthony wanted RDJ with him. (They’re really close friends; in fact, AMH is Indio’s godfather and they remain close to this day.)
Also of note: James Downey, who was/is one of SNL’s writers, is RDJ’s stepuncle.
Anyway, they weren’t kidding when they said this season is abysmal. It truly is. If you wanna watch it, all episodes are on Hulu. RDJ appears sporadically in the episodes, sometimes as a main player in the sketch, most times a glorified extra. He had a couple of regular sketches throughout the season — “Actors on Film” and “Double R”.
He was still practically a teenager, and you can tell (he looked so young and tiny compared to everybody else). Gap-toothed, sometimes awkward, but always very game and hyper as hell … pretty much like his current 48-year-old self.
Again, this season blows. You will laugh, but out of embarrassment for the people involved (I know I did).
But— if you have a craving to see baby!RDJ going through some growing pains, then this is definitely the ticket.