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.
The Rookie (1990)
Starring: Clint Eastwood, Charlie Sheen, Raul Julia, Lara Flynn Boyle
Premise: A veteran cop (Eastwood) is teamed with a rookie partner (Sheen) to nab a German crime boss (Julia) before he commits more felonies.
Why It Stinks: After spending the first part of his directorial career mostly alternating between highly commercial (and mostly enjoyable) Westerns like High Plains Drifter and action movies like Firefox, Eastwood had started to branch out in the late '80s, taking on such unlikely material as 1988's Bird, a film about jazz musician Charlie 'Bird' Parker, and 1990's White Hunter Black Heart, in which he cast himself as a Golden Age movie director modeled strongly after John Huston. While critics responded to these more mature, challenging works, audiences mostly stayed away, which may be why Eastwood was tempted into returning to the action well for an odd couple cop movie that was obviously inspired by the recent success of the Lethal Weapon films. But Lethal Weapon was powered in large part by the remarkable chemistry of Danny Glover and Mel Gibson -- Eastwood and Sheen just don't have the same spark, which makes it a slog to sit through. The casual misogyny and endless (though well-filmed) car chases don't help matter.
Midnight in the Garden of Good and Evil (1997)
Starring: John Cusack, Kevin Spacey, Jude Law, Irma P. Hall
Premise: A magazine reporter (Cusack) travels to Savannah, Georgia to write a piece on an eccentric millionaire (Kevin Spacey) accused of murder and discovers more than he bargained for.
Why It Stinks: Two years earlier, Eastwood took an almost unreadable bit of soft-core romance fiction porn, Robert James Waller's The Bridges of Madison County, and turned it into the genuinely moving story of love denied. History didn't repeat itself with his adaptation of John Berendt's non-fiction bestseller, which was a finalist for the Pulitzer Prize in 1995. In addition to failing to capture the book's mysterious tone, the movie version suffers from slack pacing and inventing an unnecessary love interest for the Cusack character, played by -- in a bit of Francis Ford Coppola-style nepotism -- the director's daughter, Alison Eastwood. Entertainment Weekly critic Owen Gleiberman spoke for the majority when he wrote, "The film feels slack, sterile, and wanly populated."
Mystic River (2003)
Starring: Sean Penn, Tim Robbins, Kevin Bacon, Laura Linney
Premise: The murder of a young woman in South Boston kicks off a police investigation that stirs up old ghosts amongst three men (Penn, Robbins and Bacon) who grew up as friends but drifted apart following a horrible crime.
Why It Stinks: Yeah, yeah, so Mystic River won Penn and Robbins their first respective Oscars and picked up dozens of other awards and accolades besides. It's still a ham-fisted, clunky adaptation of Dennis Lehane's mesmerizing novel, populated by performers who play their parts to the rafters (looking at you, Sean) and an overwrought score composed by Eastwood himself. To see Lehane done right, check out Ben Affleck's underrated directorial debut Gone Baby Gone which, while far from flawless, at least plays the material in the proper key instead of drowning its dramatic power in overacting and outsized melodramatic flourishes.
Gran Torino (2008)
Starring: Clint Eastwood, Bee Vang, Christopher Carley
Premise: A retired factory worker (Eastwood) with less-than-enlightened attitudes about race finds himself unexpectedly protecting the Asian family next door from the gang violence that's engulfing their blue collar neighborhood.
Why It Stinks: We get that Eastwood is intended to be playing a relic from another age, but does that mean all of the film's minority characters have to sound like they stepped out of a Saturday Night Live sketch? Screenwriter Nick Schenk's dialogue is rife with thudding clichés and Eastwood's depiction of gang culture is laughable when placed alongside such vivid and incisive portraits of contemporary thug life as The Wire. And while we appreciate that the finale tries to subvert Eastwood's classic screen persona as the heroic vigilante, simply turning him into a martyr isn't that much of a daring departure.
Starring: Matt Damon, Cécil De France, Frankie McLaren, George McLaren
Premise: A trio of death-obsessed characters (Damon, De France and the McLaren kids) explore the big question of what waits for mankind out there in the Great Beyond.
Why It Stinks: Eastwood famously shot the first draft of Peter Morgan's screenplay without insisting on any rewrites. That undoubtedly explains the movie's strange mélange of half-baked plot points, thinly sketched characters and one of those "everything's all connected" endings that was funnier than almost any intentional comedy released last year. If Mystery Science Theater 3000 was still on the airwaves, Hereafter would be prime viewing for the Satellite of Love of crew. (Guess we'll have to wait for the RiffTrax version instead.)
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