Clint Eastwoodis one of America’s most treasured filmmakers. Television-star-turned-movie-star-turned-lauded-director, Eastwood is among that rare breed ofdirectors whose careers span five decadesor more. Most famous as a cowboy and a cop, Eastwood has explored both the western and police procedural genres extensively—occasionally dipping into others. Over the course of his career, he has stirred up his fair share of controversy—but he’s also found just as much acclaim.
When it comes to someone with as many acting and directing credits as Eastwood, it’s difficult to watch enough of the guy’s work to get a grasp on what his best films are. After watching enough, though, some definitely stand out more than others. Eastwood has been in so many movies that lots of them can feel either very similar or like mediocre takes on the same stuff, so the ones you need to see are more than just some of his best films (though that’s a big part of it).They also demonstrate the range of subjects and genres this legend has covered, in front of the camera and behind it.In order to understand the artist, the icon, and the controversial Clint Eastwood, these movies are necessary viewing.
10’Invictus' (2009)
Directed by Clint Eastwood
Named after William Ernest Henley’s famous poem,Invictusis one ofthe best sports movies ever made. A director with such a forceful and prosaic style (not to mention a background of violent films) certainly lends well to a movie about rugby. But this is more than just a team trying to win the World Cup; the team happens to be South Africa’s Springboks, and the story takes place right after Nelson Mandela (Morgan Freemanin one of his greatest performances) was finally released from prison and put in charge of South Africa.
As Mandela begins the process of gradually healing the deep and terrible wounds of apartheid, he tries to get the national rugby team to improve and get the people rallied together. The ending toInvictusends on what many would call a deceptively positive note about South Africa’s race relations, but it’s a surprisingly moving film and certainly has a good message.
9’For a Few Dollars More' (1965)
Directed by Sergio Leone
Who knew that two guys shooting each other’s hats in the middle of the night could be so much fun to watch?Sergio Leonesure did, and he’s probably one of the only directors who could make it look as cool as it does in his second entry of the Dollars Trilogy:For a Few Dollars More. As one might expect, there’s lots of smoking, characters quietly staring at each other, beautiful images, and (of course) bullets.
The film’s pacing is so deliberate, and Leone’s vision so confident, that he can make viewers want to shoot apples off a tree (you probably shouldn’t, though). The final duel has three men in a circle, similar to how the climactic shootout inThe Good, The Bad, and The Uglywould look, andEnnio Morricone’s score is a blast—especially those haunting chimes. Clint Eastwood plays the mysterious Man with No Name again, and his portrayal of this antihero is just as cool as ever. Along with Eastwood’s chemistry withLee Van Cleefandone of the best saloon scenes ever,For a Few Dollars Moreis a must for Eastwood fans.
For A Few Dollars More
8’Juror #2' (2024)
Juror #2starts off as a pretty standard court case film, if more skillfully crafted and intense than most. But, as the title suggests, showing this largely from one particular juror’s perspective is important. Soon we learn why, and suddenly a murder case where we can’t be sure what happened adds yet another possibility into the mix.Juror #2’s dilemma is enormous, and watching Justin Kemp (Nicholas Hoult) grapple with it while the trial plays out provides a unique and intriguing nuance to the courtroom genre.
There’s a detective on the jury (J.K. Simmons) because the lawyers never asked what he does, and the prosecutor is running for DA during the trial: merely two flaws in the legal system that this movie points out. It’s hard not to love how the closing arguments are cut so that each attorney seems to be having a back-and-forth argument, making neither side seem more right than the other. Other details, like how the camera roves through each member’s vote in the backroom, elevate this film over other court dramas. If this is indeedEastwood’s final film, then it’s a hell of a way to say goodbye.
A family man serving as a juror in a high-profile murder trial faces a harrowing moral dilemma when he realizes he might be responsible for the victim’s death. As his internal struggle intensifies, he must decide whether to influence the jury’s verdict to save himself or seek justice for the accused.
7’Dirty Harry' (1971)
Directed by Don Siegel
It’s impossible to write a list of must-watch Clint Eastwood movies without including one of his most famous roles:Dirty Harry. There were several sequels to this police procedural, but the first is the only one that Eastwood fans really need to see. The Scorpio killer is based loosely off the Zodiac, and Inspector “Dirty” Harry Callahan is tasked with catching him. He doesn’t have the most orthodox approach in the world, though, and often gets into heated disagreements with the higher-ups.
Ever see a man shoot at some bank robbers while chewing on a hot dog? You can’t get much more American than that, and Dirty Harry is absolutely an American icon. Not everything in this movie has aged well (it did come out in 1971), but fans of crime thrillers will surely want to check this out anyway. DirectorDon Siegel’s stylistic flourishes set the work apart from others of its genre, and Eastwood is just as much of a tough guy as ever. Along with the famous line about feeling lucky, one could watch this just to understand its references.
Dirty Harry
6’Mystic River' (2003)
2003’sMystic Riveris yet another movie where Clint removes himself from the stage and yet displays his signature style so well that fans can easily tell that this can only be an Eastwood feature. With a stellar cast includingSean Penn,Tim Robbins, andKevin Bacon,Mystic Rivercompellingly adaptsDennis Lehane’s novel in a way that tackles trauma, revenge, loyalty, and more. It’s not enough to keep the viewers guessing; we have to care about the characters, too—a test that this film effortlessly passes. The gritty streets of Boston are hardly brought to life with such intensity.
Penn and Robbins won Academy Awards for their performances, and the movie was nominated for four other awards—including Best Director and Best Picture. Easily one ofEastwood’s best efforts of the 2000s,Mystic Rivermay not accomplish everything that it sets out to do, but it still does enough to leave an ominous imprint on the viewer’s memory.
Mystic River
5’American Sniper' (2014)
American Sniperis easily one of Clint Eastwood’s most famous films of the 21st century. It’s easy to see why; the movie is intense, superbly acted (Bradley Cooperis at the top of his game), and very well directed. Based on Chris Kyle’s memoir,American Sniper: The Autobiography of the Most Lethal Sniper in U.S. Military History, Eastwood’s adaptation offers a compelling look at how PTSD affects veterans and the overall toll that war often takes on soldiers.
Had the movie stuck to focusing specifically on Kyle’s inner struggles, it would have been more unanimously hailed an anti-war masterpiece. Unfortunately, it undermines this interpretation by featuring scenes of an enemy sniper—suggesting this is a “good guy vs. bad guy” situation. Eastwood movies usually have this dynamic, but, in this context, the structure arguably makes it look like the Iraq War was a necessary evil. Critics of the war take issue with this, and the screenplay alsotakes certain creative liberties with its source material. Along with the infamous plastic baby scene,American Sniperis a controversial work—but it’s still a powerful character study, as well as an important look at veterans' issues.
American Sniper
There’s no doubt about it:The Good, The Bad, and The Uglyis one of the greatmasterpieces of the Western genre. Over the course of three hours, director Sergio Leone captures the viewer’s imagination with sweeping landscapes, shootouts, plot twists, and a hunt for riches between three men. Eastwood’s third and final incarnation of the Man with No Name is even more entertaining than the other two, as this epic western couldn’t have us say goodbye to the character on a more magnificent scale.
The dubbing will always be annoying, the movie is built on western tropes, and it’s a bit long for those who normally don’t have the patience for long movies. Yet Sergio Leone overcomes these problems with a story so beautifully shot and suspensefully told that Eastwood fans wouldn’t be able to identify themselves as such without watching it. Along with perhapsEnnio Morricone’s most incredible score,The Good, The Bad, and The Uglyis a must.
The Good the Bad and the Ugly
3’Million Dollar Baby' (2004)
Eastwood received his second Best Director and Best Picture wins forMillion Dollar Baby, and it’s just as powerful over twenty years later as it was when it came out. Morgan Freeman andHilary Swankreceived Oscars for their performances, and Eastwood himself was given an Oscar nod for his role as a cranky old boxing manager. This man’s endless bickering with his friend (played by Freeman) is great, and the drama is even better.
The story’s genre tropes and tear-jerking moments are overpowered by the film’s blunt direction, thrilling boxing matches, and big heart. Morgan Freeman does some of his best voice-over work here, too, as in the training montage that shows Frankie training Maggie. Most important of all is the emotional bond that forms between trainer and trainee, which is truly moving. Demonstrating how Eastwood can deftly handle stories in which the characters don’t point guns at each other,Million Dollar Babyproves atruly essential Clint Eastwood picture.
Million Dollar Baby
2’Letters from Iwo Jima' (2006)
Letters from Iwo Jimamay just be Clint Eastwood’s best movie of the aughts—and even of the century. His depiction of the World War II battle of Iwo Jima was compelling enough in 2006’sFlags of Our Fathers, but Eastwood came out with that film’s companion piece later that same year and completely outdid himself in every way. The storytelling is tighter, the characters are better explored, and the inevitability of their doom creates an intensity that’s rare to find even in war movies. This is a noble tribute to the many soldiers who lost their lives, and he admirably makes sure it’s in Japanese (despite not speaking the language himself).
Ken Watanabeis terrific as General Kuribayashi, who uses unorthodox tactics to defend a beach with insufficient numbers. Meanwhile,Kazunari Ninomiyais just as compelling as Private Saigo, who cannot bring himself to end his life like his fellow soldiers (as they’re ordered to kill themselves rather than be taken prisoner). Ofall the movies Clint Eastwood has directed,Letters From Iwo Jimais especially difficult to shake.
Letters from Iwo Jima
1’Unforgiven' (1992)
If you could only choose one Clint Eastwood film to understand his influences, his aesthetic, and the power of his craft when working with an exceptional screenplay, Best Picture-winnerUnforgivenwould be it. When a sex-worker is scarred by a cruel patron, a bounty for his body is released by her associates. This captures the attention of an aging, notorious bounty hunter played by Eastwood—who enlists the help from his old partner (played by Morgan Freeman yet again) and a younger man.
For a guy who spent most of his career playing the role of the cowboy hero and antihero,Unforgivenoffered a role that strips away some of the romanticism given to those kinds of characters. The movie even features a cowardly writer who intends to publish a story about the famous gunslingers he comes across. Featuring excellent performances fromRichard Harrisand the recently-passedGene Hackmanin one of his most fantastic roles,Unforgivenrepresents the epitome of both the western and Clint Eastwood’s storytelling prowess.
