The release of a Clint Eastwood-directed Oscar hopeful has come to be one of the hallmarks of the holiday season, right up there with Black Friday sales, Christmas decorations and yet another live-action Chipmunks sequel. Since 2003's Mystic River, the iconic actor/filmmaker has released at least one prestige picture (and sometimes two) almost every year at around this time looking for box-office success and awards love. Sometimes it works (Million Dollar Baby, Letters From Iwo Jima) and other times, it doesn't (Flags of our Fathers, Hereafter). Based on the underwhelming reviews and grosses of his latest film, J. Edgar, an expansive biopic of the legendary FBI director written by Oscar-winning Milk scribe Dustin Lance Black and starring Leonardo DiCaprio as J. Edgar Hoover, this is shaping up to be one of his off years.
With two Oscars and 31 directing credits to his name (his 32nd , J. Edgar opened in theaters yesterday) there's no question that Clint Eastwood has secured his legacy as one of Hollywood's premiere filmmakers. But when you produce that many movies over the course of a multi-decade career, there are bound to be a few flops... just ask Woody Allen. And going by the majority of reviews, J. Edgar may be one of the films that's omitted from Clint's career highlights reel. We'll have our own thoughts about the film next week, but in the meantime here are our picks -- in chronological order -- for Eastwood's five worst movies as a director.