4. Tropic Thunder
Often seen to lack substance in certain roles, Stiller proves with Tropic Thunder that hes more than just a silly face, though he is that too. Tropic Thunder is his satirical stab at Hollywood; written, directed and produced by Stiller himself, its proof that hes better than some of the bog-standard comedic roles that he sometimes chooses for himself. Here though, he plays a direct parody of the cash-cow actor he's often taken for. Not as consistently hilarious a movie as you might hope, Stiller nevertheless attempted something bigger, better and bolder and ultimately darker than most of the mainstream Hollywood comedy that came before it, and arguably pulled the genre out of its Will Ferrell shaped rut. For that reason, Stiller must be thoroughly commended and his role within easily earns a place this side of the list.