Zoolander. It's nice to finally see the film that created a bunch of memes, most notably "What is this? A center for ants?!"
I can recommend it as a well-made comedy/satire. It didn't feel like anything groundbreaking. Maybe it was at the time of its release, I really don't know, but as far as I'm concerned its popularity is just luck of the draw
Ben Stiller seems to have a track record of playing characters where he is the butt of the jokes and I really appreciate that. His catalog of roles is a great starting point for a list of comedy gold movies.