Madame Chana said something in another discussion that jogged a personal observation--
Why is this phenomenon? And why does it work sometimes and sometimes not? Who are actors that play the same tired stereotype in every role they take on?
I'll nominate a few: Woody Allen, Angelina Jolie (tired of your tough, angry, wounded bitch schtick), Jennifer Aniston, and Seth Rogen (likable, but always the awkward, hapless underdog that luck smiles on after unleashing a shitstorm).