I've not seen the Wolf of Wall Street yet, but from what I've read about it, this seems like an appropriate comparison. That said, a man of humble beginnings that rises up out of his station is not a terribly unique plot line. Still, it seems like actors will sometimes end up on a streak of similar roles. I wonder how much this is happenstance and how much is cultural or by choice? I recall Bill Murry going through his sad old man phase, the result of which was fantastic films with extremely similar characters: Lost in Translation, Rushmore, Broken Flowers etc.
Bill Murray's sad old man phase is probably my favorite phase of his. All of those movies are incredible, especially Lost in Translation, which is also probably the best acting job from Scarlett Johansson as well.
I agree, I am a fan of all of those films. But I still have a soft spot for Meatballs.