Clint Eastwood's 9 Least Badass Roles

[caption id="attachment_147906" align="alignleft" width="300" caption="Warner Bros."]Trouble With the Curve[/caption]

Clint Eastwood is the last, lonely representative of a mythical breed — the badass. Oh sure, there are other tough-guy actors out there (Stallone, Schwarzenegger and other assorted Expendables) but they're all a little too oiled, chiseled and ready for their Men's Health cover shoots. Eastwood is old-school; the kind of gunslinger who survived his shoot-outs not by having bigger biceps, but because he's leaner, meaner and smarter than the bad guy. Men fear his squint, not his heavy artillery or super powers.

But though he's made a permanent cigarillo-chomping, growling, feel-lucky-punk badass crater on all of pop culture (there's no Wolverine or Jason Statham without Clint), Eastwood hasn't always played it hard and flinty. He's been beat up, left for dead, stuck behind a desk and lost and confused on the range. Though he seemed keen to end his acting career as cantankerous and trigger-happy as it began — "Get off my lawn!" — he appears to have changed his mind and opted to remind audiences of his softer side in "Trouble With the Curve." There's no Walt Kowalski or William Munny in Gus the baseball scout, who shouts a lot but cuts a sad figure as he peers through his eyeglasses and yells at his prostate.

Eastwood has always relished undermining his cool persona by befriending orangutans, letting Sondra Locke and Shirley MacLaine punch him and ... well, yelling at chairs. Here are nine other examples where Clint's been less than a pure unfiltered badass.

9. "Space Cowboys" (2000)

[caption id="attachment_147908" align="alignright" width="150" caption="Warner Bros."]Space Cowboys[/caption]

The premise of "Space Cowboys" is that they're all too old for NASA, so you can't roll your eyes at this line-up of elderly action heroes. Nor can you call Eastwood's Dr. Frank Corvin a wimp. He's an astronaut, engineer and test pilot! He's a different kind of tough, a no-nonsense man who wields a pocket protector and slide rule over a Magnum .44. Brains, stamina and a knack for math help him fight off the forces of old age, competition from young astronauts, bureaucracy, Soviet warheads and the deadly chill of space. He's like Dirty Harry's nerdier cousin, or NASA's Mohawk Guy without the style.

8. "Pink Cadillac" (1989)

[caption id="attachment_147909" align="alignright" width="150" caption="Warner Bros."]Pink Cadillac[/caption]

Eastwood's attempts at action-comedy are a mixed bag, but he failed at both when he took on the part of bounty hunter Tommy Nohawk. He does pack a gun but relies more on costumes, tricks and snark to get the job done. He's good at his job until this one case, where he's completely buffaloed by a bail-skipping Bernadette Peters. Yes, that's right. Eastwood, who took on Lee Van Cleef and lived to tell about it, finds himself blinded by Peters' sequins and outwitted by her adorable lisp. He tries to remind us he's Clint Eastwood with a forest shoot-out at the end but the damage was already done.

7. "Blood Work" (2002)

[caption id="attachment_147910" align="alignright" width="150" caption="Warner Bros."]Blood Work[/caption]

All action heroes do one (or two, or three) flicks where their cops and soldiers should have been drawing pension instead of guns. "Blood Work" is Eastwood's major "Why isn't this guy golfing already?" moment. To be fair, his Terry McCaleb is a retired FBI profiler, but only because he actually suffered a heart attack in the line of still-too-old-for-it duty. A heart transplant puts Eastwood back on the trail of a serial killer, but he's a fragile man, wheezing through all his chase and fight scenes. It's uncomfortable to watch, though arguably not in the tense and sympathetic way the movie intends.

6. "White Hunter, Black Heart" (1990)

[caption id="attachment_147911" align="alignright" width="150" caption="Warner Bros."]White Hunter Black Heart[/caption]

Eastwood's John Wilson is meant to be an ersatz John Huston (complete with the affected "I drink your milkshake!" accent) and the epitome of strutting machismo. He plays hard, drinks harder and is on a quest to shoot anything that moves. The film is meant to be a deflation of that attitude, and it is ... but that also means seeing Eastwood-as-Wilson falter in the face of an enraged elephant. None of his cops and gunslingers would have been dumb enough to bug a mama elephant to prove their manhood, recognizing (as Wilson belatedly does) that posturing is for wimps and cowards.

5. "The Beguiled" (1971)

[caption id="attachment_147912" align="alignright" width="150" caption="Universal"]The Beguiled[/caption]

Eastwood has an intriguing cinematic habit of being beat up by women, but there's only one film where a gang of women completely emasculate him, and that's "The Beguiled." His Yankee soldier John McBurney is an unrepentant slimeball who thinks he can sleep his way through a Southern girl's school and survive the Civil War. But the girls don't take kindly to his bed-hopping and take their revenge by drugging him, tying him to the kitchen table and playing "Operation." Yes, it's as creepy and gruesome as it sounds, and a wonderful example of an Eastwood character being betrayed by his own swagger.

4. "Honkytonk Man" (1982)

[caption id="attachment_147914" align="alignright" width="150" caption="Warner Bros."]Honkytonk Man[/caption]

This sad and folksy story finds Eastwood drinkin', coughin' and lovin' his way across the Great Depression, hopin' to become a famous country singer. Red Stovall is certainly a hardscrabble guy who can fend for himself (otherwise he'd have been dead long before this set of adventures), but he's no match for tuberculosis. It's one of Eastwood's rare "average guy" roles and remains a traumatizing one for fans who never wanted to see their favorite outlaw coughing up blood.

3. "Paint Your Wagon" (1969)

[caption id="attachment_147915" align="alignright" width="150" caption="Paramount"]Paint Your Wagon[/caption]

Tough guys can sing (just ask Frank Sinatra, Dean Martin or Hugh Jackman), but sadly Clint Eastwood and Lee Marvin couldn't. That didn't stop them from belting out a number of western-themed tunes in "Paint Your Wagon," a bizarre and corny dramedy about gold mining and wife-sharing. Eastwood's "I Talk to the Trees" has gone down in tuneless infamy, but while it's a dorky moment, it's also a gutsy one. How many action stars do you know that would croon a line like, "Her heart was made of holidays"?

2. "Play Misty For Me" (1971)

[caption id="attachment_147918" align="alignright" width="150" caption="Universal"]Play Misty For Me[/caption]

The same year Dirty Harry strode out to ask punks if they felt lucky, Eastwood allowed himself be cut to ribbons by Jessica Walter. His DJ Dave thinks he's the coolest guy in Carmel and swaggers right into a one-night stand with Walter's Evelyn ... but then Evelyn reveals she's been stalking him and that she won't take kindly to being dumped. A terrified Dave must now flee from Evelyn's screams, threats, manipulations and attempted murder. Eastwood has rarely been as vulnerable as he is in "Misty," where he's just trying to catch a bit of sleep before a butcher knife nearly makes off with half his skull.

1. "The Bridges of Madison County" (1995)

[caption id="attachment_147919" align="alignright" width="150" caption="Warner Bros."]The Bridges of Madison County[/caption]

If you're looking for the softest and sweetest moment of Eastwood's entire acting career (and allegedly the one that's closest to his real-life personality), it's here. As photographer Robert Kincaid, he's all rugged charm and gentle gestures. He's a man who picks bouquets of flowers, helps with dinner, dances with a lady in the kitchen and never slams a screen door. When he breaks down and sobs after Francesca refuses to run away with him, you're hard-pressed to remember any hardened antihero from his past.