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4. "The Royal Tenenbaums"

The incredible critical success of Rushmore in 1998 gave Wes Anderson carte blanche to make pretty much any movie he wanted as a follow-up. He opted to make huge ensemble movie about a family of former child prodigies struggling to life normal lives as adults. Ben Stiller played Chas Tenenbaum, a business genius that can't get over the tragic death of his wife. It's a stellar film that only gets better with repeat viewings.