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Favourite movie collaborations:
1) Clint Eastwood / Sergio Leone / Ennio Morricone - These three are responsible for some of the greatest westerns ever made. The combination of Eastwood's often imitated but never duplicated performances, Leone's signature visual style and Morricone's beautiful scores is hard to beat.
2) Akira Kurosawa and Toshiro Mifune - Won't pretend I've seen all their collaborations, but based on Yojimbo, The Seven Samurai, and Rashomon alone, I think these guys did pretty well for themselves. Guess they had something of a falling out later on, but I believe they mended fences at a friend's funeral (just a few years before they themselves both died).
3) Brian O'Halloran and Jeff Anderson (aka Dante and Randall from Clerks) - I don't enjoy Kevin Smith's stuff as much as I used to, but these guys essentially made his career. Anderson has brilliant comedic timing (especially for a non-actor), and O'Halloran is great at playing the morose sad-sack, but still being likeable.
80s teen comedy... yeah - I'll echo and say "Breakfast Club is NOT a comedy!"
A lot of good films were already mentioned... John Cusack is a favorite for the trifecta of "Sure Thing," "Better Off Dead," and "One Crazy Summer." (Sorry - Say Anything also not a comedy)
But I don't think one of my all time favorites was mentioned - Real Genius! Love that flick!