Clint Eastwood’s 10 Coolest Movie Roles Of His Career

Clint Eastwood is one of cinema’s acting and directing titans, and he’s played some of the coolest characters over his astoundingly long career.

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Famed actor and director Clint Eastwood has been making movies since 1955, and he’s still going strong with 2021’s Cry Macho. Over the past six and a half decades, Eastwood has played tough-as-nails outlaws in a series of unforgettable westerns, before varying up his repertoire with a series of modern-day action flicks, dramas, and even some comedy.

During that time, he’s created some of the most iconic characters in movie history, who still stand the test of time so many years later. Eastwood’s rugged presence and take-no-guff attitude is largely what made these characters so memorable, and it’s doubtful anyone could have played them quite the same.

Steve Everett (True Crime, 1999)

True Crime saw Eastwood hang up his traditional tough-guy role in favor of something different. Here, he portrayed Steve Everett, a journalist trying to prove the innocence of a death row inmate scheduled for execution. It didn’t rank very high with critics, who felt that Eastwood (who also directed the film) was the wrong choice for the role.

Over time, the film has managed to garner a better reception, particularly due to Eastwood’s performance. It’s memorable in the fact that it came at a midway point in his career when Eastwood had already directed a cache of previous films.

Frankie Dunn (Million Dollar Baby, 2004)

Clint Eastwood directed and starred in this 2004 mega-hit featuring Hilary Swank, who turned out one of the best dramatic performances of the 2000s. The story involves a female boxer who hits the big time under the tutelage of Eastwood’s character, Frankie Dunn. It remains one of the actor’s most profitable films, grossing over $216 million dollars against a $30 million dollar budget.

Dunn is a character who ends up becoming not just a mentor, but a father figure to Swank’s character Maggie. Million Dollar Baby is an emotional rollercoaster of soaring highs and crushing lows, with Dunn acting as the character who gets the rawest deal of the bunch.

Joe Kidd (Joe Kidd, 1972)

The 1970s saw Eastwood continuing to star in a string of westerns before he’d eventually start breaking out into more contemporary roles. Joe Kidd was one of his best, where he played the titular ex-bounty hunter who gets roped into hunting a Mexican revolutionary.

Eastwood played a less gritty character than his usual western movie fare, blending toughness with a sense of understated civility. As a result, Eastwood managed to craft a character somewhere between Will Munny from Unforgiven, and the Preacher from Pale Rider.

Frank Horrigan (In The Line Of Fire, 1993)

In this memorable action thriller, Eastwood played Frank Horrigan, an aging Secret Service agent who takes up a spot on a detail to protect the current sitting President from the threat of assassination. His opponent is Mitch Leary, a killer who plays on Frank’s guilt over his inability to save President Kennedy from assassination decades prior.

Eastwood injected a bit of Harry Callahan into the role, without the rebelliousness that would have seen him booted off the Secret Service detail. The character was smartly written, and presented Eastwood in a badass role with a surprising amount of vulnerability, which was rare for him.

Frank Morris (Escape From Alcatraz, 1979)

Eastwood headed up this tense prison thriller as Frank Morris, an extremely intelligent convict who schemes up a way to get out of America’s most notorious prison. While he plans his escape along with several other inmates, he’s forced to contend with the machinations of a sadistic Warden with an eye out for trouble.

The film is a masterpiece mixture of tension, excellent pacing, and even some humor thrown in for good measure. Eastwood turned out one of the best performances of his entire career, making Frank Morris one of his most memorable “bad guy to root for” characters.

Walt Kowalski (Gran Torino, 2008)

Capitalizing on his own age, Eastwood played the memorable Walt Kowalski in this popular 2008 film, which he also directed. The character was a Korean War veteran and widower with a serious chip on his shoulder, who befriends a young Asian man named Thao.

Over the course of the film, Kowalski softens his bigoted attitude and becomes a grandfather figure to Thao. The film is a beautiful testament to how people can change in spite of their upbringing. As a result, Walt Kowalski remains one of Eastwood’s best characters.

The Preacher (Pale Rider, 1985)

Clint Eastwood’s defining mark lies in how many western movies he’s starred in, and there are a lot. However, few are as memorable as Pale Rider, where he played the mysterious Preacher, a do-gooder with a quick draw. He earns the adoration of young Megan Wheeler and her mother, the former of whom believes was sent by God to help her family.

Eastwood played the Preacher with a sense of hardness and kindness. He’s clearly a man with a dark past, but he’s also a benevolent character out to do as much good as he can in a very harsh world. It would turn out to become one of Eastwood’s best western films.

Blondie (The Good, The Bad And The Ugly, 1966)

Few cowboy films have as much staying power as the classic The Good, The Bad And the Ugly, directed by famed Spaghetti Western filmmaker Sergio Leone. Here, Eastwood played the allegorical “Blondie,” one part of a trio of opportunists seeking to get their hands on a buried fortune.

While Eastwood was not the direct central character of the film, he was one of its linchpins. The timeless theme song mixed with the unusual and inventive narrative helped propel Eastwood into stardom, paving the way for a string of hits to follow in later years. It continues to rank high as one of the most pioneering westerns of all time.

Will Munny (Unforgiven, 1992)

Eastwood directed and starred in this incredible, gritty western, where he played Will Munny, a former outlaw grieving the loss of his late wife, who takes a hit contract to help pay for his farm. Along the way, he gets wrapped up in his old lifestyle, and the brutal code of honor that went along with it.

Munny is such an unforgettable character thanks to Eastwood’s rustic and unapologetic performance. In contrast to the Spaghetti Western films that made him famous, Unforgiven was far more grounded in a sense of reality and plausibility, and Munny was the vehicle that allowed the audience to glimpse it.

Harry Callahan (Dirty Harry, 1971)

Undoubtedly Eastwood’s most iconic and prolific role, Harry Callahan embodied the kind of rebellious, rough-edged attitude of police officers forced to endure America’s rampant and horrific 1970s crime epidemic. The character was a proverbial middle finger against emerging political correctness that had begun seeping into law enforcement, leading to both good and bad results.

Callahan was a street cop who walked the beat, knew the players, and understood the risks. He scoffed at political hypocrites and opportunistic lawyers dictating policy from their ivory towers and gated communities, and kept his focus on taking down the bad guys before they harmed more innocent people. His methods were dirty, and he crossed the line, giving audiences one of the most quotable anti-heroes in cinema.

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