10. Coogan’s Bluff (1968)
Think the Clint archetype, but in New York City.
Save your Pace salsa jokes. Coogan’s Bluff just works, and does wonders to prove the durability of Eastwood’s gritted-teeth caricature. It even shows faint signs of levity in Eastwood’s steely demeanor. Ironically, it’s a “damn hippies” sort of procedural, and Clint slides through like a cobra amidst flowers. But honestly, this is just fun-as-hell pulp.
The fish-out-of-water film is the stuff of hackwork nowadays, but Eastwood did it with such confidence. You’ve seen the urban drug avenger, but with a way-out-West cowboy in the thick of it? Walt Coogan’s the name, and he’s the Arizona lawman dispatched to New York City (one complete with pool hall fights, happenin’ LSD weirdness, make-out sessions, and all sorts of freaks trying to kill Coogan). The almost clichéd work of Eastwood feels like it really can fit into any movie here. Clint’s a fighter, a lover, a cowboy, a cool guy, and above all, a star.
Who’s Directing: Well, well, well, if it isn’t Don Siegel. This would be the first of five films Siegel made with Eastwood, and Siegel would later become his directing mentor. Best buds, these two.
Essential Eastwood: Apologies for the second-hand YouTube quality here, but in the year of Bullitt, Coogan’s final bike chase is criminally underseen. Proves that Clint just looked great in action.
09. Every Which Way but Loose (1978)
For the sake of honesty, we’ll just say it now – this movie’s dumb as a rock. It’s that buddy actioner with Eastwood and a beer-swilling orangutan named Clyde. Perhaps you’ve seen the stills of Clyde giving the finger online? Share it via text if you get the chance! The sequel’s even sillier, and it gave us a Ray Charles and Clint Eastwood duet about beer. But damn it, we love Every Which Way but Loose anyhow and the way in which Clint pals around with his co-star in self-effacing fashion. It’s a farce with its brow hung low as Eastwood stars as Philo, the trucker/brawler just a’ drinkin’ and a’ punchin’ his way through the American West.
While you can guess the general beats – orangutan makes a silly, Philo bops other boys in bars – the overall mood is so easygoing. Clyde socks Nazis (suck it, alt-right), Ruth Gordon pisses and moans about Oreos, and Eastwood knocks ‘em dead in fist fights with his girl and his ape by his side. Every studio passed on this, but Eastwood thought it would be fun in the wake of Smokey and the Bandit and other good, ol’ boy comedies. Adjusted for inflation, this is still Clint’s biggest hit – over $500 million in 2018 numbers.
Who’s Directing: James Fargo got his start as an assistant director on TV movies before eventually graduating to his first feature film, The Enforcer (the third Harry Callahan film). Perhaps it’s to Fargo’s credit that Eastwood has been quoted as saying that Clyde (Manis, in real life) was the most natural actor he’s ever worked with. That takes good direction and guidance, one reckons.
Essential Eastwood: Oh, Clyde steals the show for sure. But if you’ll pardon the expression, Eastwood’s a helluva second banana.
08. Where Eagles Dare (1968)
Brian G. Hutton’s spectacle holds up in a way best described through onomatopoeia, Where Eagles Dare is boffo kablammo! It’s an insane, stunt-filled war epic (one that Tarantino willfully riffed upon for his Inglourious Basterds). And Eastwood is simply B.A.D. ass in it, but he does it in a minor key. Clint kills, early and often, but with a modest intensity. He arguably disappears into it, acting as a perfect utility for action filmmaking, a believable face and presence for larger-than-life set pieces and scenarios. Next to Richard Burton’s exorbitant theatrics and Brian Hutton’s arsenal of stunt and effects men, Eastwood just slides into this World War II event role with spy-like gamesmanship.
Who’s Directing: Brian G. Hutton would reunite with Eastwood a mere two years later for Kelly’s Heroes. Hutton got Eastwood to do his own stunts on this sucker.
Essential Eastwood: Look at Eastwood, just hanging back. Taking it in. And doing that thing where the quiet dude might be the most intimidating one in the room. Even with hype from British forces, Eastwood just keeps it cool. That, right there, is presence. And it’s a testament to his performance when so many hyperbolic explosions and so much action occurs, yet his demeanor feels hypnotic and almost like a reprieve.
07. The Outlaw Josey Wales (1976)
The film school kids are still dueling over Josey Wales’ perceived left- and right-wing politics. In the wake of Saigon, Josey Wales focused on post-war trauma, Native reparations, and deep resentment for the government that screams … well, Eastwood would prefer you decide for yourself. Sneaky Pete. While known as conservative in real life, his films tend to be best read as moral fables — extended thought scenarios that look less to make a single statement on something and instead reflect on extraordinary circumstances or reality-suggested troubles. (By Eastwood’s own admission in documentaries, any bias or political reads were incidental and only help to strike up conversations.)
Josey Wales had soul, regret, and a conscience, and all he was looking for was closure (read: revenge) after his family’s massacred. The Missouri farmer wanted action against the Union men that killed his family. It a harsh premise, and Clint was rarely as good at selling those kinds of dilemmas as he is here. Pale Rider, High Plains Drifter, and especially Unforgiven play in the same turf, but rarely has he been this intense and satisfying and just plain tough in the role.
Who’s Directing: This was Eastwood’s fifth directorial effort and perhaps the earliest signs of philosophical life in his Westerns. But here’s the crazy story: Eastwood replaced the original director and writer, Philip Kaufman, at the 11th hour, prompting the DGA to create an “Eastwood Rule” banning actors from taking over productions. All over an alleged boy’s fight for the affections of co-star Sondra Locke. Ugh, fellas.
Essential Eastwood: Remember how much John Wayne hated Native Americans? Well, Eastwood, and by virtue Josey Wales, had more modern, complicated, and compelling drives to interact with Native Americans.
06. The Beguiled (1971)
Eastwood, the onscreen manipulator of women. 1971 was a curious year. Eastwood doubled down as a clueless DJ in his directorial debut, Play Misty for Me, and The Beguiled saw Eastwood as a “blue belly” Union deserter and wolf in the chicken coop that is a Confederate girls boarding school. But while the former falls into the problematic at times, The Beguiled still flies as a nervy work of Southern gothic and haunted, perverse eroticism. And Clint was up to the task of being the gross, pathetic, and cunning McBurney in one of his least remembered, least likable, and most underappreciated roles. And boy, does he get what’s coming to him. It’s a balancing act, as Eastwood nails broken-dog pity, womanizing evil, and deserving amputation that leaves him in agony. It’s a familiar sort of evil for the ages.
Who’s Directing: Clint and Don Siegel, at it again. Apparently, Eastwood was interested in the novel for some time, as he was fascinated by the source’s notions of male desire to castrate female power. Curious given his macho man M.O., no?
Essential Eastwood: Before the Coppola remake, a colleague reminded me of the “old enough for kisses” line, and naturally, I retched. Hey, if that’s not effective villainy, I don’t know what is.