There are so many great movies to recommend but I’d almost have to say that your first choices in any attempt to fill the gaps in your moviegoing experience should be the quadrafecta of brilliant Christopher Guest mockumentaries:
This is Spinal Tap
Waiting for Guffman
Best in Show
A Mighty Wind
The first film on this list is technically a Rob Reiner film, since he was the director and all, but it’s the brilliance of the writing, the improv chops of the actors, and, yes, the actual musicianship of the members of the band, that make it truly shine. This is Spinal Tap is the template for the three Christopher Guest-directed films that followed more than a decade later. Waiting for Guffman is at least as good as Spinal Tap, although that’s certainly sacrilege to some, and Best in Show and A Mighty Wind are worthy successors even if they don’t quite live up to the greatness of the first two films. I mean, how often can you make a masterpiece? It doesn’t really matter if you don’t miss the mark by much.