Every Clint Eastwood Movie of 21st Century, Ranked Worst to Best

Look, when you’re talking about Hollywood legends, Clint Eastwood is in a league of his own. The man is 94 years old and still making movies, and that’s just insane! Since the year 2000, he’s directed 18 films that range from absolute masterpieces to… well, let’s just say some interesting experiments.

From intimate character studies to massive war epics, Eastwood has kept busy, proving why he’s got two Best Director Oscars sitting on his shelf. Some of these films are straight-up classics, while others? Not so much. But here’s the thing, even his misfires are worth talking about.

So grab your popcorn, because we’re diving into every single Clint Eastwood movie from the 21st century, ranked from “what were they thinking?” to “absolute perfection.”

18 The 15:17 to Paris (2018)

Okay, so here’s where Eastwood got a little too experimental for his own good. He decided to cast the actual real-life heroes who stopped a terrorist attack on a Paris-bound train to play themselves. Noble idea? Absolutely. Good movie? Not really. The problem is that Spencer Stone, Anthony Sadler, and Alek Skarlatos are genuine heroes but not actors, and it shows (painfully).

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
The 15:17 to Paris	Warner Bros. Pictures, Village Roadshow Pictures, Malpaso Productions	5.3/10	Critics: 24% Audience: 37%	$57.1 Million (via Box Office Mojo)

We spend forever watching awkward backstory scenes before finally getting to the thrilling 15 minutes everyone came to see. It’s like Eastwood forgot that documentaries exist for a reason. The authentic heroism these guys showed deserved a better movie, maybe with actual actors who could, you know, act. Even at just 94 minutes, this one feels way longer than it should.

You can currently stream The 15:17 to Paris on platforms like Netflix, Prime Video, or Fandango at Home (formerly Vudu). You can also rent or buy the movie through services like Apple TV and Google Play. 

17 Cry Macho (2021)

At 91, Eastwood proved he still had the guts to star in his own movies, playing a washed-up rodeo star who heads to Mexico to rescue his ex-boss’s teenage son. There’s something genuinely touching about watching Eastwood at this age, all weathered and reflective, exploring what masculinity means when you’re past your prime.

The film’s got this gentle, melancholic vibe that works in moments, but let’s be real, it moves slower than a Sunday drive and hits every predictable beat you’d expect.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Cry Macho	Malpaso Productions	5.7/10	Critics: 57% Audience: 64%	$16.5 Million (via Box Office Mojo)

It’s basically Gran Torino-lite with sombreros and roosters. Not terrible, just… forgettable? Which is weird for an Eastwood film. The movie’s heart is in the right place, and there’s poignancy in Eastwood’s performance, but the whole thing needed more punch to really land.

You can watch Clint Eastwood’s film Cry Macho by subscribing to Max (formerly HBO Max).

16 Hereafter (2010)

So Eastwood decides to make a supernatural drama about the afterlife with Matt Damon as a reluctant psychic. Yeah, that happened. It’s one of his weirdest choices, and honestly? It doesn’t quite work. The movie follows three people connected by death and the great beyond, and while it’s beautifully shot and occasionally moving, it never really finds its footing.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Hereafter	The Kennedy/Marshall Company, Malpaso Productions, Amblin Entertainment	6.5/10	Critics: 48% Audience: 38%	$106.9 Million (via Box Office Mojo)

That opening tsunami sequence is absolutely spectacular (genuinely jaw-dropping), but the film never recaptures that visceral power. Critics said it best: it straddles the line between

poignant sentimentality and hokey tedium.

Damon tries his best, and you can see Eastwood attempting something different, but the whole thing feels like a mismatch between director and material. Still, you’ve gotta respect a filmmaker willing to swing for the fences this late in his career.

15 Blood Work (2002)

Eastwood plays an ex-FBI agent with a brand new transplanted heart who’s tracking down a serial killer in this adaptation of Michael Connelly’s novel. It’s… fine? That’s really the best word for it. The movie’s competently made (Eastwood’s always been a solid craftsman), but there’s nothing here that makes it stand out.

Critics complained about “lethargic pacing,” and they weren’t wrong. The film absolutely tanked at the box office, making just $31.7 million against a $50 million budget (via Box Office Mojo), which must’ve stung.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Blood Work	Malpaso Productions	6.4/10	Critics: 52% Audience: 40%	$31.7 Million (via Box Office Mojo)

Jeff Daniels is genuinely creepy as the killer, and Eastwood does his usual stoic thing, but the whole movie feels like it’s going through the motions. It’s the kind of thriller that used to fill theaters in the ’90s but by 2002 felt pretty stale.

You can buy Blood Work on Apple TV to download or rent it on Amazon Video, Apple TV online.

14 J. Edgar (2011)

Leonardo DiCaprio goes full method as FBI director J. Edgar Hoover, and while his performance is fantastic, the movie around him just never clicks. Eastwood and screenwriter Dustin Lance Black try to cram decades of American history (the Lindbergh kidnapping, blackmailing MLK, Hoover’s closeted sexuality) into one film, and it ends up feeling rushed and unfocused.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
J. Edgar	Imagine Entertainment, Malpaso Productions, Wintergreen Productions	6.5/10	Critics: 44% Audience: 44%	$84.9 Million (via Box Office Mojo)

The aging makeup on DiCaprio drew lots of eye-rolls, too; it’s more distracting than convincing. The film speeds through these massive historical moments without giving any of them room to breathe. It’s frustrating because you can see the great movie hiding in here somewhere.

DiCaprio’s doing incredible work showing Hoover’s complexity and paranoia, but the movie’s all over the place. When your best element is fighting against your structure, you’ve got problems.

Currently, you can buy J. Edgar to download on Apple TV or rent it on Amazon Video, and Apple TV online.

13 Jersey Boys (2014)

Eastwood tackling the Tony Award-winning musical about The Four Seasons should’ve been a slam dunk. Instead? It’s weirdly flat. The performances are solid enough, and obviously the songs are classics (“Sherry,” “Big Girls Don’t Cry,” “Walk Like a Man”), but the film never breaks free from feeling like a filmed stage production.

Where’s the energy? Where’s the pizzazz? It’s competently made, sure, but “competent” isn’t what you want from a movie about one of the most exciting bands of the 1960s.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Jersey Boys	RatPac-Dune Entertainment, GK Films, Malpaso Productions	6.8/10	Critics: 51% Audience: 62%	$67.6 Million (via Box Office Mojo)

The story’s compelling (four guys from Jersey making it big and dealing with the fallout), but Eastwood’s typically restrained direction works against the material here. Musicals need a certain spark, a joy that just never shows up. It’s not bad, just surprisingly forgettable for an Eastwood joint.

You can buy Jersey Boys to download or rent it on Amazon Video, Apple TV, and Fandango At Home.

12 The Mule (2018)

Eastwood came out of acting retirement at 88 to play Earl Stone, an elderly horticulturist who becomes a drug mule for a Mexican cartel. The premise alone is fascinating (based on the true story of Leo Sharp), and Eastwood brings real pathos to this guy who’s messed up his whole life and is trying to fix things when it’s way too late.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
The Mule	Imperative Entertainment, Bron Creative, Malpaso Productions	7/10	Critics: 70% Audience: 67%	$174.8 Million (via Box Office Mojo)

The problem? The tone’s all over the place. One minute it’s a comedy, next it’s a heavy drama, then suddenly it’s a thriller. Bradley Cooper shows up as the DEA agent on his tail, and their scenes work well, but the movie never quite finds its groove. That said, audiences ate it up! Eastwood proved he’s still got box office mojo even if the movie itself is messy.

You can watch The Mule by purchasing or renting it from platforms like Amazon Video, Apple TV, Plex, Fandango at Home, and Google Play. The movie is also available on Netflix and can be streamed on Roku devices.

11 Space Cowboys (2000)

Four aging astronauts get called back for one last mission? Sign us up! Eastwood assembled an absolute dream team (Tommy Lee Jones, Donald Sutherland, and James Garner) for this genuinely fun adventure flick.

Yeah, the plot’s got every cliché in the book, but who cares when the chemistry between these legends is so good? They’re clearly having a blast playing off each other, and that energy is infectious.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Space Cowboys	Village Roadshow Pictures, Clipsal Films, Malpaso Productions, Mad Chance Productions	6.5/10	Critics: 78% Audience: 53%	$128.8 Million (via Box Office Mojo)

The film takes its time building these characters before blasting them into space, and that patience pays off. When the action kicks in, the special effects hold up surprisingly well even now. It’s not trying to be anything more than an entertaining crowd-pleaser, and it succeeds completely. Sometimes that’s enough, especially when you’ve got this level of star power elevating the material.

You can currently rent Space Cowboys on Amazon Video online.

10 Invictus (2009)

Morgan Freeman as Nelson Mandela? That’s perfect casting right there. This inspirational sports drama shows how South Africa’s 1995 Rugby World Cup victory helped unite a divided nation after apartheid.

Matt Damon earned an Oscar nomination playing team captain François Pienaar, and the chemistry between him and Freeman is electric. Sure, the story follows the typical sports movie playbook (you know exactly where it’s going), but Eastwood’s measured direction and the performances elevate it beyond the formula.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Invictus	Revelations Entertainment, Mace Neufeld Productions, Malpaso Productions, Liberty Pictures	7.3/10	Critics: 76% Audience: 75%	$122.2 Million (via Box Office Mojo)

Roger Ebert nailed it, calling this

a very good film with moments evoking great emotion.

The rugby sequences are thrilling even if you don’t understand the sport, and the film’s message about unity and forgiveness hits hard. It’s the kind of uplifting drama that reminds you why Eastwood’s been doing this for 50+ years.

Currently, you are able to buy Invictus streaming on Apple TV as a download or rent it on Amazon Video, Apple TV online.

9 Changeling (2008)

Based on the horrifying Wineville Chicken Coop murders, this period thriller has Angelina Jolie fighting against a corrupt LAPD after they try to pass off some random kid as her missing son.

It’s dark, twisted, and Jolie’s performance is absolutely devastating. She’s a mother pushed to the absolute edge. Eastwood crafts this gothic nightmare, showing how institutions can crush ordinary people, and the anger in this film is palpable.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Changeling	Imagine Entertainment, Malpaso Productions, Relativity Media	7.7/10	Critics: 61% Audience: 82%	$113.3 Million (via Box Office Mojo)

The critics were split on it, but many called it “flawless” and “emotionally powerful.” The period detail is impeccable, and the story’s righteous fury about police corruption and media manipulation feels eerily relevant today. It’s one of Eastwood’s few female-driven films, and he handles it with surprising sensitivity. Definitely an underrated gem in his filmography that deserves more love.

You can buy or rent Changeling on Amazon Video, Apple TV, and Fandango At Home.

8 Richard Jewell (2019)

Paul Walter Hauser’s performance as Richard Jewell absolutely breaks your heart. This security guard discovers a bomb at the 1996 Atlanta Olympics, saves countless lives, and then gets absolutely destroyed when the FBI and media decide he’s actually the bomber.

Eastwood’s sympathetic direction captures how quickly an ordinary guy can get chewed up by the system. The film feels super relevant in today’s media landscape, where reputations get demolished on Twitter before anyone checks the facts.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Richard Jewell	Malpaso Productions, Appian Way Productions, Misher Films, 75 Year Plan Productions	7.5/10	Critics: 77% Audience: 96%	$44.6 Million (via Box Office Mojo)

Hauser makes Jewell so human (awkward, earnest, just wanting to do the right thing) that when everything falls apart, you feel it in your gut. Sam Rockwell and Kathy Bates provide excellent support as his lawyer and mother. It’s a powerful reminder that the distance between hero and villain is just one news cycle.

You can buy Richard Jewell on Amazon Video, Apple TV, Fandango At Home to download or rent it on Plex, Amazon Video, Apple TV, Fandango At Home online.

7 Gran Torino (2008)

This was supposed to be Eastwood’s final acting performance (until The Mule came along), and what a way to go out! Playing Walt Kowalski, a prejudiced Korean War vet who forms an unlikely friendship with his Hmong neighbor, Eastwood created one of his most memorable characters.

The film grossed a whopping $270 million worldwide and made 78-year-old Eastwood the oldest leading man to hit #1 with a $29 million opening weekend.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Gran Torino	Warner Bros. Pictures, Village Roadshow Pictures, Double Nickel Entertainment, Malpaso Productions	8.1/10	Critics: 81% Audience: 90%	$270 Million (via Box Office Mojo)

Yeah, some people criticized how it handled race, but the film’s meditation on redemption and the lasting cost of violence really hits. Eastwood’s growling performance and that iconic “get off my lawn” moment became instant classics. It’s a powerful examination of how toxic masculinity and violence haunt us, wrapped in a surprisingly tender story about cross-cultural friendship and sacrifice.

You can buy Gran Torino on Amazon Video, Apple TV, and Fandango At Home for download.

6 Flags of Our Fathers (2006)

The American side of Eastwood’s ambitious Iwo Jima diptych follows the men who raised that famous flag and how they got exploited for war bond sales afterward. It’s a fascinating, brutal look at how we manufacture heroes and commodify their trauma for propaganda.

The film’s less focused than its Japanese companion piece, but it offers something really provocative: showing the gap between the heroic image we create and the messy, bloody reality these guys lived through.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Flags of Our Fathers	DreamWorks Pictures, Malpaso Productions, Amblin Entertainment	7.1/10	Critics: 76% Audience: 69%	$65.9 Million (via Box Office Mojo)

Ryan Phillippe, Jesse Bradford, and Adam Beach lead a strong ensemble cast. The movie deconstructs American heroism in ways that probably made some viewers uncomfortable, which is exactly the point. War is hell, and making celebrities out of traumatized soldiers for political purposes? That’s a different kind of hell entirely.

You can buy Flags of Our Fathers on Apple TV for download or rent it on Amazon Video.

5 American Sniper (2014)

Bradley Cooper completely transformed himself to play Chris Kyle, the deadliest sniper in U.S. military history, earning an Oscar nomination in the process. Eastwood’s direction is lean, powerful, and doesn’t waste a single frame exploring Kyle’s struggles with PTSD and trying to reconcile his battlefield identity with civilian life.

The film became a massive cultural lightning rod. Some saw it as pro-war propaganda, others as a tragic portrait of what war does to soldiers. Either way, it dominated 2014, becoming the year’s highest-grossing movie at $547.7 million worldwide.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
American Sniper	Village Roadshow Pictures, RatPac-Dune Entertainment, Mad Chance Productions, 22nd & Indiana Pictures, Malpaso Productions	7.3/10	Critics: 71% Audience: 84%	$547.7 Million (via Box Office Mojo)

The action sequences are intense, but it’s the quiet moments showing Kyle’s disconnection from normal life that gut you. Say what you want about the politics, but Eastwood crafted a technically brilliant and emotionally devastating war film.

Currently, you are able to watch American Sniper streaming on Amazon Prime Video Free with Ads.

4 Juror #2 (2024)

At 94 years old, Eastwood just dropped what might be his finest late-career work. This gripping legal thriller stars Nicholas Hoult as a juror who realizes mid-trial that he might be responsible for the death being prosecuted. It’s taut, morally complex, and masterfully crafted, everything you want from a courtroom drama.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Juror #2	Dichotomy Films, Malpaso Productions	7/10	Critics: 93% Audience: 90%	$27 Million (via Box Office Mojo)

The film feels like a culmination of Eastwood’s career-long fascination with moral ambiguity and institutional failure. Critics absolutely loved it, calling it,

a crackerjack legal/moral thriller

Warner Bros. weirdly gave it only a limited release (a bizarre choice for a 93% Rotten Tomatoes film), but audiences who found it have been raving. It’s proof that Eastwood’s still got it after all these years.

You can watch Juror #2 on Max, or you can also purchase or rent the movie on digital platforms like Apple TV and Amazon Video.

3 Sully: Miracle on the Hudson (2016)

Tom Hanks playing Sully Sullenberger, the pilot who safely landed a plane on the Hudson River? Perfect casting. But here’s what makes this special: Eastwood doesn’t just retell the “Miracle on the Hudson” story everyone knows.

Instead, he crafts this tense examination of judgment, doubt, and institutional scrutiny. The nonlinear narrative keeps you on the edge of your seat even though you know exactly how it ends.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Sully: Miracle on the Hudson	Village Roadshow Pictures, Ratpac-Dune Entertainment, Flashlight Films, The Kennedy/Marshall Company, Malpaso Productions, Orange Corp	7.4/10	Critics: 85% Audience: 84%	$243.8 Million (via Box Office Mojo)

Hanks delivers this beautifully understated performance, showing a humble man who just did his job but gets second-guessed at every turn. The recreation of the emergency landing is both technically brilliant and emotionally devastating. Aaron Eckhart is perfect as co-pilot Jeff Skiles. This film deserves way more love than it got; many think it’s one of Eastwood’s best.

Currently, you are able to watch Sully: Miracle on the Hudson streaming on Amazon Prime Video.

2 Mystic River (2003)

Eastwood’s first masterpiece of the new millennium is this dark, haunting crime drama that reunites three childhood friends after one of their daughters is murdered. Sean Penn, Tim Robbins, and Kevin Bacon deliver career-defining performances. Penn and Robbins both won Oscars, making this the first film since Ben-Hur to win both Best Actor and Best Supporting Actor.

Brian Helgeland’s adaptation of Dennis Lehane’s novel crackles with tension and explores how childhood trauma echoes through entire lives. The film’s examination of vigilantism, masculine violence, and the price of silence is absolutely brutal.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Mystic River	Village Roadshow Pictures, Malpaso Productions, NPV Entertainment	7.9/10	Critics: 89% Audience: 89%	$156.5 Million (via Box Office Mojo)

Critics praised it for being a better Dennis Lehane adaptation than Martin Scorsese managed. Everything clicks here: the performances, the direction, the atmosphere. It’s proof that Eastwood had plenty of gas left in the tank and was entering a new creative peak.

You can buy Mystic River for download or rent it on Amazon Video, Apple TV, and Fandango At Home.

1 Million Dollar Baby (2004)

Here it is: Eastwood’s absolute crowning achievement of the 21st century. This devastating boxing drama swept the Oscars with four wins, including Best Picture, Best Director, Best Actress for Hilary Swank, and Best Supporting Actor for Morgan Freeman.

What starts as a traditional underdog sports story transforms into a profound meditation on sacrifice, euthanasia, and unconditional love. Swank’s performance as Maggie Fitzgerald is absolutely incredible. You completely believe her transformation from trailer park waitress to championship boxer.

Movie	Production House	IMDb	Rotten Tomatoes	Box Office
Million Dollar Baby	Lakeshore Entertainment, Epsilon Motion Pictures, Malpaso Productions, Ruddy Morgan Organization	8.1/10	Critics: 90% Audience: 90%	$216.7 Million (via Box Office Mojo)

Freeman provides the heart and soul as Eddie “Scrap,” and Eastwood himself is perfectly cast as the cantankerous trainer Frankie. That ending? It sparked massive debate and still haunts people today.

Critics and audiences both rated it 90% (a rare alignment). This is Eastwood stripping away all sentimentality to reveal raw human truth, proving that at 74, he could still create his most powerful work yet.

So, there you have it. 18 films spanning over two decades from one of cinema’s true legends. From the absolute peaks of Million Dollar Baby and Mystic River to the experimental misfires like The 15:17 to Paris, Eastwood’s 21st-century filmography shows a director unafraid to take risks and tackle difficult subjects.

What do you think? Did we get the ranking right? Is Gran Torino too low? Does Sully deserve the #3 spot? Drop your thoughts in the comments below! We want to hear which Eastwood films hit you the hardest and which ones you think are overrated.

Don’t forget to share this article with your fellow film buffs and let us know in the comments which Clint Eastwood movie deserves a rewatch!