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The Truman Show - 1998
U.S. Box Office: $125 million
Actual nominees that year: "Shakespeare in Love," "Elizabeth," "Life is Beautiful" "Saving Private Ryan," "The Thin Red Line"
Winner: "Shakespeare in Love"
Justification: "The Truman Show" was not only a box office and critical hit, but received three Oscar nominations including best director. That category in particular usually means the picture was "that close" to getting into the final five. What killed it? Perhaps star Jim Carrey's obnoxious Golden Globe winning speech a few weeks before? Or too much competition? It's unclear, but with ten nods, it's clearly in.
Other potential nominees: "Gods and Monsters," "Bulworth," "Affliction," "There's Something About Mary"