Clint Eastwood: His 10 Best Roles

Limiting Clint Eastwood's greatest roles to a mere ten films is a damn near Sisyphean task. Over 55 years of movie-making, the steely-eyed actor/director has created so many indelible characters, it's hard to imagine them all coming from the same mortal man.
With the release of the supernatural thriller 'Hereafter,' it's a good time to look back on some of Eastwood's most memorable characters. We did have two rules: Only one movie could be considered per series -- hence the omission of 'A Fistful Of Dollars,' 'Magnum Force' and the like -- and films directed by, but not starring, Eastwood were discounted ('Bird,' 'Mystic River,' etc.). The debate begins ... now.

10. 'Hang 'Em High' (1968)
If you're going to hang Clint for stealing cattle and murder, don't leave before he's actually dead. After Jed Cooper (Eastwood) mistakenly gets the vigilante justice treatment and is subsequently saved by a passing lawman, he's hired as a deputy marshal and ordered to round up assorted criminals, including the men that tried to kill him. Eastwood says more in this western than in the entire "Man With No Name" trilogy, and his neck rope-burn, an eternal souvenir of his attempted murder, remains one of the actor's iconic visual symbols.

9. 'Million Dollar Baby' (2004)
At 74, Eastwood picked up another Best Picture and Best Director Academy Award (and Best Actor nomination) for his story of a boxing trainer who takes on an aging female boxer (Hilary Swank) and helps her grow into a skilled fighter. The 'Rocky'-esque story, with one major difference in the end, was a critical darling and the most popular of Eastwood's later directorial efforts.

8. 'In the Line of Fire' (1993)
The 1980s was not Eastwood's finest acting era -- besides 'Sudden Impact,' 'Tightrope' and 'Pale Rider,' you could pretty much write off the entire decade -- but the one-two of 1992's 'Unforgiven' and this Wolfgang Petersen thriller resuscitated the actor's flagging career. As Frank Horrigan, an aging Secret Service agent still tormented by his perceived failure to guard John F. Kennedy's assassination, Eastwood matches wits with John Malkovich in one of his best roles (a role originally offered to Robert De Niro). A potentially rote story becomes tense and mesmerizing thanks to the two leads.

7. 'Play Misty For Me' (1971)
Laying the groundwork for a glut of 1980s female stalker films, Eastwood's directorial debut finds him as a California jazz deejay who meets some female company at a bar. Good news: He goes home with her. Bad news: She's the same woman who calls in to his show repeatedly asking him to play "Misty" and crazily shows up at his home on numerous visits. With our stalker friend becoming more and more unhinged, 'Misty' is part-Hitchcockian thriller, part action film and entirely a good case for monogamy.

6. 'Outlaw Josey Wales' (1976)
Called by Eastwood himself one of the "high points of [his] career," this revisionist western finds the actor as a farmer-turned-Civil War-confederate guerrilla who refuses to surrender to the U.S. Army and gets hunted as, well, an outlaw by the man who slew his family. Wales is a (slightly) kinder Man With No Name, yet still able to inspire fear with a singular glint of the eye.

5. 'High Plains Drifter' (1973)
Eastwood's second directorial effort revisits the Old West, drawing from his earlier westerns but introducing a supernatural theme from screenwriter Ernest Tidyman ('Shaft,' 'The French Connection'). Known only as The Stranger for much of the film, the ambivalent and contradictory loner is arguably Eastwood's biggest anti-hero of his career. 'Drifter' combines the traditional work of Eastwood mentor Sergio Leone with suggestions of reincarnation and spirits, making this one of the best additions to the genre. And it, of course, inspired this.

4. 'Escape From Alcatraz' (1979)
Nobody escapes from "The Rock," right? Nearly 20 years before Michael Bay's fiasco with Sean Connery and Nicolas Cage, Eastwood, portraying real-life criminal genius Frank Morris, attempts to flee the seemingly foolproof island prison with two other inmates. Shot in and around the actual prison, director Don Siegel, who previously teamed up with Eastwood on 1971's 'Dirty Harry' among others, infuses 'Alcatraz' with riveting realism and a surprisingly effective backstory. As a character drama, Eastwood and Siegel deftly depict the juxtaposition of the sadistic with the mundane on The Rock. But it's the film's titular escape that ultimately makes this one a classic.

3. 'Unforgiven' (1992)
By the early 1990s, the western had long since gone to the bar, seen a prostitute, rustled up horses and been shot dead in some ill-conceived duel or shootout. Leave it to Eastwood to help revive a moribund genre -- sorry, 'Young Guns' -- with this 1992 film that won four Oscars, including Best Picture and Best Director. Eastwood is William Munny, an outlaw-turned-bounty-hunter who, along with his protégé (Jaimz Woolvett) and friend (Morgan Freeman), hunts down a man wanted for slashing a prostitute's face. Eastwood bought the script in the early 1980s and waited until he was old enough to play Munny as a man who could look back on his life. When Eastwood tells Woolvett, "It's a hell of a thing killin' a man," bolstering the film's anti-violence subtext, he proves yet again that it's the content, not the quantity, of the words that makes all the difference.

2. 'Dirty Harry' (1971)
If Inspector Harry Callahan was a real cop, he'd have been demoted to Meter Maid in the first ten minutes of the series. We're fans of the entire series -- even 'The Dead Pool' remains unfairly maligned -- but the original film became the now-stereotypical template for every authority figure who hates authority. Axel Foley, Martin Riggs, McGarnagle, and countless other subsequent cops all owe a debt to Eastwood's politically incorrect, misanthropic, quick-to-violence Inspector. It's a testament to the film's massive influence that many classic scenes in the series now unwittingly border on parody -- the fed-up chief, the verbal mindscrewing of perps, the constant wisecracks, etc. -- but it was Callahan that started it all.

1. 'The Good, the Bad and the Ugly' (1966)
The last ten minutes of Sergio Leone's masterpiece is enough to put this at the top of the list. The final, and best, film in the "Man With No Name" trilogy still remains the archetypal spaghetti Western, with cinematographer Tonino Delli Colli's sweeping landscape shots (in Techniscope!), Ennio Morricone's haunting, iconic score and the greatest use of editing in a film ending to this day. Eastwood reprises his role as the Man With No Name, setting up a career of action-over-words characters, and squares off against a Mexican bandit (Eli Wallach) and merciless bounty hunter (Lee Van Cleef) in a search for stolen gold. More than 40 years later, the film remains perfect. Enough reading. Just watch.

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