Make our day: Clint Eastwood's 20 best performances, ranked

In his directorial debut, Eastwood plays late-night DJ Dave Garver, who runs into a bit of a stalker problem in "Play Misty for Me." Eastwood strived to play Garver as a regular guy, and not one who is fast on the draw or with a sneer, making him instantly cast away from type, which was largely the point. Opposite Jessica Walter (yes, the future Lucille Bluth) as his stalker, Eastwood shines in his freshman directorial attempt with a smoldering presence that he would recreate in a way in 1984's "Tightrope."

Once considered the hardest prison to escape from, Alcatraz has always been more about legend than fact. That idea carries through in "Escape From Alcatraz," a mostly fictional account of the escape of three inmates who virtually vanished upon their exit being discovered. Here, Eastwood plays inmate Frank Morris, and because so little is known about Morris in real life, Eastwood uses it as an opportunity to create a hard but honorable character whose distaste of the semi-sadistic warden (Patrick McGoohan) serves as a catalyst for the brazen escape.

A lighthearted tale marrying the Old West with the more modern requires a lighter touch, and Eastwood is more than game as "Bronco" Billy McCoy, the head of a traveling circus of malcontents masquerading as cowboys. Here Eastwood puts away his sneer for the sardonic and delivers a solid performance as a man who is fighting to preserve his place while struggling to recognize that place may be firmly rooted in the past.

For the last (and best) of Eastwood's three turns as the Man with No Name, "The Good, the Bad and the Ugly" features Eastwood as his most stoic and slyly mischievous. This time around, "Blondie" is stuck with outlaw trickster Tuco (Eli Wallach) as they make their way through a desert and a Civil War battleground in search of a grave with $200K in Confederate gold. 

Now for something completely different, Eastwood trades his guns and steely sneer for a camera and a heart firmly on sleeve in his adaptation of Robert James Waller's bestseller "The Bridges of Madison County." As Robert Kincaid, Eastwood effectively romances a lonely housewife (Meryl Streep) in a whirlwind affair that changes both their lives in the short time they spend together. While a bit late in life to take on the role of romantic lead, Eastwood does more than an admirable job as a November heartthrob. 

The first appearance of "The Man with No Name," Eastwood cuts an archetype for himself in his first leading role that would not only define much of his career but also the genre as a whole. Joe, as he's known informally in the film, is a man of few words but big actions and presents the image that changed how audiences looked at Westerns going forward.

A thinly veiled take on director John Huston, Eastwood doesn't choose to ape the actor/director but rather echo his sensibilities as John Wilson, a Hollywood director whose blood runs red with adventure, and he plays out his fantasies in the African veldt. Eastwood knows his Wilson is possibly more villain than hero, but he never allows him to be a one-note character — or one immune to self-reflection and possibly change. The film's final moments show Wilson as a haunted man but also one who has a greater appreciation than he's ever known.

At the age of 63, Eastwood proved still capable of being the action hero, but in Wolfgang Peterson's "In the Line of Fire," he settles into his phase as aged leading man in a role that, much like in "Unforgiven," plays on his limitations as an offset to his tenacity. As Frank Horrigan, a Secret Service agent who failed to save John F. Kennedy, he finds himself facing yet another potential assassin (John Malkovich, still not a jewel thief) as he races against the clock, both literally and figuratively, to ensure he doesn't lose another president.

Eastwood takes a unique, albeit darker path on his days as Sergio Leone's "Man with No Name" in "High Plains Drifter." As "The Stranger," Eastwood is once again called on to save a town — one that has more than a few secrets of its own. Like his work for Leone, Eastwood plays most things close to the chest with a limited amount of dialogue, but much of his silent intensity feels like a precursor to what he would later unleash in "Unforgiven."

Eastwood's penultimate Western is a performance that bookends with that in "High Plains Drifter." Whereas the Stranger in "Drifter," Eastwood evoked an angel of vengeance, in "Pale Rider," he plays the other side of the coin as an angel of mercy, albeit with a similar skill for gunfighting. As "Preacher," Eastwood is a bit more accessible than in the former role, giving his character a bit more depth as he balances faith with a six-shooter. Despite the perceived paradox in that balance, Eastwood more than capably pulls off the idea of a gunman for God.

In the follow-up to Oscar-darling "Unforgiven," Eastwood's more understated (albeit cantankerous) turn as a Texas Ranger on the heels of an escaped convict (Kevin Costner) who goes on the run with a child hostage is both unexpectedly tender and warmer than one expects. It's not for Red Garnett to storm in guns blazing at this point in his career, and Eastwood drives that point home by focusing on wry wit and a world weariness that makes his supporting character endearing and memorable.

In "Tightrope," Eastwood could've played the cop role as a pastiche of his work as Harry Callahan, but instead he manages to let audiences in a bit deeper as his Wes Block is forced to investigate sex crimes that are a bit closer to his own proclivities than he would like. In that, Eastwood delivers an uncharacteristic level of vulnerability that was surprising even for him.

Eastwood turns a moving performance as depression-era country/western singer Red Stovall, who takes his hard living and hard luck and goes off on one last adventure to perform at the Grand Ole Opry in Nashville, Tennessee. Stovall is dying of tuberculosis, but Eastwood doesn't choose to go somber and morose, instead playing Stovall as the sort of complicated but lovable personality who is certainly larger than his own reality and yet every bit as self-destructive. 

While it might be natural to laugh off Eastwood's "monkey movies," "Every Which Way But Loose" and its 1980 sequel, "Any Which Way You Can," Philo Beddoe, a hard living, hard drinking, hard everything bare-knuckle boxer was more sensitive than expected, showing a softer side in his affection for his family, including orangutan Clyde. Eastwood, while certainly in a middle stage of his career, never felt himself above the material, making what could be considered an absurd pairing of man and ape into something truly enjoyable.

His first lead in an American Western, Eastwood shines as wronged rancher Jed Cooper, lynched by mistake by a group of cattlemen and scoundrels for a crime he didn't commit. Cooper survives his lynching and is allowed to go after his captors by a hanging judge (Pat Hingle), whose desire to maintain order sometimes throws the concept of true justice into question. Eastwood is equal parts dashing and determined here, showing a certain versatility that works even more in his favor than in Leone's trilogy.

A surprising late-career turn from Eastwood comes in the form of the bigot-with-a-heart-of-gold Walt Kowalski in "Gran Torino." A retiree who built a wall around himself in his later years, Kowalski finds himself tearing down that wall as he befriends an Asian teen and his family after the teen tries to steal Walt's prized car. Walt is Harry Callahan in everything but name, and Eastwood plays him with a sense of completion as a man whose view of the world twisted him as he grew old. But his decency and sense of justice never fail to guide him.

Eastwood takes a page from the book of every crusty boxing trainer as Frankie Dunn in his Academy Award-winning "Million Dollar Baby." Eastwood forms a special bond with a boxer he initially didn't want to train (Hilary Swank). But what separates Eastwood's performance from those we've already seen is what happens when his boxer suffers a freak accident that forces him to not only emote in a way he hasn't in film before but also do it in a believable and heartbreaking way.

The sum total of all of Eastwood's Western roles are given an exclamation point in his portrayal of former gunfighter turned farmer William Munny in the Academy Award-winning "Unforgiven." Bill Munny has long retired from the outlaw game, but a new set of circumstances drums up the worst version of his old self, something Eastwood emotes with his signature steeliness. It leads to a climax that presents the deadliest character Eastwood ever played: one whose compassion, or even sense of justice, melts away, leaving only a hardened killer who will absolutely get his revenge.

In a career full of Western roles, Josey Wales may arguably be Eastwood's best. A modest Missouri rancher conscripted into war following the murder of his family by Union soldiers, Wales seeks only revenge. But as the war draws to a close, Josey's war only burns on. Eastwood gives his usual stoic Western performance, but his take on Josey, while defiant, also speaks to a man who yearns for peace, from within and without. 

Harry Callahan is, and maybe always be, a polarizing figure — part action hero, part commentary on the public's fear and hatred of due process. When "Dirty Harry" was released in 1971, urban crime was a hot topic, with public complaints that criminals never got the justice they deserved (of course, this wasn't completely true, especially in urban communities), and in many ways, Eastwood's portrayal in this first film walks a fine line, more so than in the later conservative fantasies that would comprise the four following sequels. That said, it's hard not to love the guy while fully knowing the consequences of doing so.