Clint Eastwoodis a towering figure in the history of cinema. His groundbreaking performances as “The Man With No Name” in Sergio Leone’sDollars Trilogyand as Harry Callahan in theDirty Harrymovie series effectively created the Spaghetti Western and neo-noir film genres. Meanwhile, his move behind the camera to the director’s chair has led to a succession of modern classics, including his Oscar-winning genre moviesUnforgivenandMillion Dollar Baby. Yet there’s more to Eastwood’s career than his headline big-hitters, such as the selection of his movies now free to watch on Amazon’s Prime Video showcases.

Eastwood isn’t the typecast caricature of morally ambivalent antiheroeshe’s made out to be. There’s also more to his understanding of cinema than the economy of words he’s famous for as a director. He’s a profoundly intelligent filmmaker, able to shape his characterizations and directions to the needs of whatever movie he’s working on. What’s more, he’s a rare example of an Americanactor but even better directorwho’s consistently demonstrated empathy with the plight of Native Americans, and who’s been willing to cross the artificial threshold separating Italian and Spanish-speaking filmmakers from Hollywood’s Anglo-American hegemony. Eastwood’s repertoire on Prime Video highlights these sides of his work.

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5Reel Injun (Documentary)

2009

Reel Injunisn’t a Clint Eastwood movie per se, but it illustrates Clint Eastwood’s pioneering role in the recharacterization of Native Americans in Hollywood cinema. Eastwood makes a brief appearance in the documentary to discuss working withNative American actorsChief Dan George, in his own 1976 masterpieceThe Outlaw Josey Wales, and Adam Beach to portray the life of war hero Ira Hayes inFlags of Our Fathers.

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Western movies remain popular and stand the test of time, but several iconic movies have been criticized for historical inaccuracies and portrayals.

But the legendary Western actor and director is alsoconspicuous by his absence, from the offensive depictions of Native Americansin dozens of the movies thatReel Injun’s Cree-Canadian director Neil Diamond examines. UnlikeJohn Wayne, Eastwood seldom took part in moviesthat propagated harmful and inaccurate stereotypes about Native Americans. Moreover, his fruitful working relationship with various tribal communities of North America is testament to his exceptional role in Hollywood breaking these stereotypes.

Ennio Morricone Composer

4Escape from Alcatraz

1979

Don Siegal’s biographical thrillerEscape from Alcatrazportrays a real-life 1962 escape from the notorious maximum-security prison on California’s Alcatraz Island. Eastwood plays the ingenious ringleader of the prison escape, Frank Morris, who’s forced to contend with the violent rapist and fellow inmate Wolf while befriending other prisoners who were unlucky to find themselves on the wrong side of the law.

Never mindThe Shawshank Redemption,Escape from Alcatrazis the original and the best modern prison escape film.

Clint Eastwood photgraphing Meryl Streep in The Bridges of Madison County

For realism, suspense and a spectacular prison break, forgetThe Shawshank Redemption.Escape from Alcatrazis the original and thebest modern prison escape film, with Eastwood showing his range as a performer by portrayinga sympathetic and understated herotrying to evade the heavy hand of the law.

3Ennio (Documentary)

2021

Enniois a glorious celebration of the great Italian film composer Ennio Morricone, much of which is narrated poetically by its subject. Eastwood features in short interview clips, to share his views on the innovations of Morricone’s soundtracks in genre filmmaking. It’s thanks to the composer that the most iconic image of Eastwood as an actor is the death stare of hisgreatest Western character, “The Man with No Name,” soundtracked by Morricone’s famous theme music laden with pan flutes inThe Good, the Bad and the Ugly.

This documentary premiered at Venice Film Festival in 2021, but only became more widely available a year later. For this reason, it’s largely slipped under the radar. But it’s well worth watching, even if just forbehind-the-scenes insights into Sergio Leone’s Spaghetti Westernsstarring Eastwood shared by many of those involved in their production.

Split image of Meryl Streep on the poster for Postcards from the Edge and with Jonah Hill in Don’t Look Up

2The Bridges Of Madison County

1995

Starring Meryl Streep alongside Eastwood as its female lead,The Bridges of Madison Countymarked a significant change of pace for the actor-director when it was released in 1995. A heartfelt romance about a brief wartime encounter that stayed with Streep’s protagonist Francesca forever, the movie is different from anything Eastwood, who plays Francesca’s love interest Michael, has directed before or since.

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Meryl Streep has shared the screen with such similarly iconic stars as Robert De Niro, Clint Eastwood, and Shirley MacLaine.

Streep andEastwood give two of the best performances among any of the director’s movies. Their onscreen chemistry madeThe Bridges of Madison Countya winner with critics and audiences alike. Fans of Clint Eastwood who want to seea softer side of the filmmakershould start here.

Clint Eastwood and Morgan Freeman on horses in Unforgiven

1Unforgiven

1992

On the other hand, surely Eastwood’s best movie available for free on Prime Video is a dispassionate Western about a stone-cold killer. Marking the start of his late-career renaissance both as an actor and a director,Unforgivenis a gripping philosophical exploration of what it means to be a hero in the Western sense. In this way, themovie is not only one of Eastwood’s best, but is arguably the one that defines his career more than any other. It explores the anti-hero personas he developed in his earlier years with fresh eyes, from the stance of a director as well as an actor.

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Clint Eastwood is the epitome of the iconic cowboy in classic Westerns, portraying characters that elevate the quality of these timeless films.

His protagonist, William Munny, isa former outlaw and bounty hunter forced to come out of retirementto provide for his family. The requisite saloon bar showdowns ensue, but are rendered in novel forms that manage to pay homage to classic Westerns while bringing something new to the genre.Clint Eastwoodproves himself a master of the genre behind the camera as well as in front of it, in a movie John Ford at his best would have been proud to make.

Clint Eastwood as Blondie aims a gun in The Good The Bad and The Ugly

Headshot Of Clint Eastwood In The AFI Fest 2011