Dirty Harry: 5 Ways He’s Clint Eastwood’s Best Character (& 5 Alternatives)

After starring in Don Siegel’s gritty police thriller Dirty Harry, Clint Eastwood reprised the title role of Inspector “Dirty” Harry Callahan in a grand total of four sequels, from Magnum Force to The Dead Pool. Callahan is arguably Eastwood’s greatest role, making full use of his strengths as an actor and giving him plenty of dramatic material to sink his teeth into, but there are a bunch of other close contenders.

The actor’s decades-long career has been lined with iconic characters. From Sergio Leone’s spaghetti westerns to his own directorial efforts, Eastwood has played a ton of roles that have come close to matching Callahan as a screen icon.

10. Dirty Harry Is The Best: He’s A Quintessential Antihero

Clint Eastwood is best utilized when he’s given less than perfect people to play. His gruff demeanor and icy stare are beautifully matched to antiheroes who do questionable things and try not to look back.

Harry Callahan is a quintessential antihero, breaking away from the police’s codes of conduct if they stand in the way of what he sees as the right course of action.

9. Alternative: Frankie Dunn

Although Million Dollar Baby was marketed as a female version of Rocky, it becomes a much more depressing affair after its midpoint twist in which its protagonist, budding boxer Maggie Fitzgerald, is disabled at the beginning of her promising career.

Clint Eastwood co-stars as Maggie’s trainer Frankie Dunn, who champions her through her first few fights and then has to contend with the heartache of her sudden paralysis.

8. Dirty Harry Is The Best: He’s Eastwood’s Darkest Character

The best acting plumbs the darkest depths of the human soul, from Martin Sheen’s turn as Captain Willard in Apocalypse Now to Al Pacino’s portrayal of the corruption of Michael Corleone in The Godfather trilogy.

Clint Eastwood is one of the world’s greatest actors in terms of playing dark roles. As a cop who will torture suspects without thinking twice, Harry Callahan is easily Eastwood’s darkest role.

7. Alternative: Josey Wales

The title role in The Outlaw Josey Wales is a challenging one, as he’s a farmer whose family is murdered by the Union during the Civil War who then joins a Confederate guerrilla army in pursuit of vengeance.

In addition to directing The Outlaw Josey Wales as a magnificent study of the Civil War, Eastwood starred as one of his most iconic characters.

6. Dirty Harry Is The Best: He’s Morally Complex

Unlike a lot of gun-toting detectives in Hollywood cinema, Harry Callahan isn’t depicted as a clear-cut hero. He’ll bend the law in order to catch a bad guy or he’ll feel justified in killing if he thinks it will prevent more killing.

The audience isn’t expected to be on Harry’s side at every turn, but the moral gray area in which he operates means he’s never anything less than compelling.

5. Alternative: Walt Kowalski

In Gran Torino, Eastwood stars as Walt Kowalski, a Korean War veteran who now lives in a neighborhood filled with Korean gangsters. As he’s caught in a gangland conflict, he confronts his own prejudices and makes the ultimate sacrifice in a harrowing finale.

The actor’s ice-cold glare was perfect for the role of Kowalski. He plays the role as a typical crotchety old neighbor, but with a dark side that’s as clear as day.

4. Dirty Harry Is The Best: He Has Most Of Eastwood’s Quotable Lines

Over the course of an incredible career that spans seven decades and counting, Clint Eastwood has uttered a ton of memorable lines on the big screen that have been quoted by fans ever since.

But the majority of his most beloved quotes belong to Harry Callahan, like “Go ahead, make my day,” “A man’s got to know his limitations,” and “You’ve gotta ask yourself one question: ‘Do I feel lucky?’ Well, do ya, punk?”

3. Alternative: William Munny

Eastwood gave the perfect swansong to the outdated genre that spawned his career with the bleak revisionist western Unforgiven. Years after turning his back on a life of killing to lead a simple farming existence, William Munny is reluctantly recruited for one last gig as an outlaw.

The movie is a grisly tale of redemption as Munny strives to exact brutal vigilante justice, but it also takes every chance to remind viewers that he’s no hero.

2. Dirty Harry Is The Best: A Lot Of Eastwood’s Subsequent Roles Emulated Harry

After the success of Dirty Harry, the title character became Clint Eastwood’s defining role, to the point that many of his subsequent roles were written to emulate Harry’s blunt, unconventional style.

Eastwood had made his name as a cowboy in Italian westerns and playing an iconic detective on the streets of San Francisco ensured him a career in contemporary American thrillers.

1. Alternative: The Man With No Name

Between 1964 and 1966, Clint Eastwood teamed up with Sergio Leone to create three of the greatest westerns ever made. With A Fistful of Dollars, Leone recontextualized Kurosawa’s Yojimbo for the Wild West and pioneered the spaghetti western. With The Good, the Bad, and the Ugly, he perfected the genre.

Across all three movies, Eastwood played the fabled Man with No Name, a gunslinging drifter who chases bounties and plays gangs against each other.