The 7 Best Clint Eastwood Movies of the 21st Century, Ranked


Summary

  • Eastwood excels in diverse genres, from westerns to biopics, enhancing his reputation as a brilliant storyteller.
  • Cry Macho, though not his best work, showcases Eastwood’s mastery in bringing heartwarming stories to life with depth and emotion.
  • Eastwood’s films like Changeling and Mystic River tackle heavy themes, portraying the complexity of human relationships and societal flaws.

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Clint Eastwood isn’t just one of the greatest directors in film history, but one of the most versatile. Eastwood is most closely associated with the western genre, and for good reason; after starring in Sergio Leone’s beloved The Man With No Name trilogy of A Fistful of Dollars, For A Few Dollars More, and The Good, The Bad, and The Ugly, he directed many iconic westerns. Pale Rider, High Plains Drifter, The Outlaw Josey Wales, and the Best Picture winner Unforgiven were responsible for injecting a new sense of life into the genre, and ensured that Eastwood would forever be associated with his infamous outlaw persona. Of course, Eastwood has directed nearly 40 films, and not all of them are westerns.

Interestingly, he followed up his wins at the Academy Awards for Unforgiven with a versatile series of projects that reflected his growth as a storyteller. His work over the course of the last two decades has signified that Eastwood’s filmography should be appreciated as not just the work of a great western director, but the output of a filmmaker capable of biopics, action films, comedies, dramas, and much more. Roger Ebert noted that Eastwood “has a supremely intelligent artistic sensibility,” and Eastwood himself has stated that he continues “working because I learn something new all the time.” Here are the best Clint Eastwood movies of the 21st century, ranked.

Updated May 16, 2024: This article has been updated by Soniya Hinduja with more brilliant movies directed by Clint Eastwood.

12 Cry Macho (2021)

Certainly not his finest work till date, Cry Macho is heartwarming enough to remind us why Clint Eastwood is considered a master of storytelling. The movie takes place in 1979. Eastwood plays the role of a washed-up rodeo star named Miko who takes a job from his former employer to bring his teenage son home from Mexico. As the unlikely duo embark north, they face a series of challenges. The boy reluctantly forms a bond with Miko, and he teaches him what it means to be a good man.

Cry Macho Explores Familiar Themes with a Fresh Lens

In what may be his final leading role in a Western, Eastwood infused that assured touch of a seasoned auteur. Which is perhaps why a simple tale of an unlikely connection forming between two individuals against the odds seems so profoundly moving. The intimate moments between Eastwood and Eduardo Minett added depth and perfection. Cry Macho proves that the director can find nuance even in well-trod genres, which is what makes it so enjoyable.

11 Hereafter (2010)

Hereafter

Release Date
October 22, 2010

Cast
Cecile de France , Thierry Neuvic , Cyndi Mayo Davis , Lisa Griffiths , Jessica Griffiths , Ferguson Reid

Hereafter explores themes of life and death and life after death. It tells three parallel stories that are somehow intertwined. Marie is a French television journalist who narrowly escapes death, Marcus is a young London boy who loses the person closest to him, and George is a blue-collar American with a special connection to the afterlife, meaning he can communicate with the dead. When their paths cross, their lives and their perception of death changes profoundly.

Hereafter Contemplates Life’s Biggest Questions

A poignant and soulful drama directed, co-produced, and scored by Eastwood, Hereafter is a complex story. Stars Cécile de France, George McLaren, and Matt Damon bring reserved strength to their roles of people affected and awakened by their connection to mortality and each other. The movie also bravely tackles life’s biggest question, one we have all wondered about at some point in time. Again, it may not be as reliable and compelling as Eastwood’s other outings, but Hereafter manages to be tender and delicate, which is an Eastwood trademark too.

10 Changeling (2008)

Set in 1928 Los Angeles, Changeling centers around Christine Collins, a single mother who returns home one day to find her son missing. She reaches out to the LAPD, who eventually find a boy claiming he is Christine’s son, but she insists he is not. The police dismiss her claims and facing a corrupt system and a rotten city for her gets harder by the day.

Changeling Is a Crime Thriller That Resonates Emotionally

Based on the real-life Wineville Chicken Coop murders, Changeling is among the few female-driven movies directed by Eastwood. It is enriched with heavy themes of societal flaws and injustices. Angelina Jolie gives a brilliant performance as a mother on an unstoppable quest to get past certain institutions’ dark influences and discover the truth about her son. Paired with supporting turns from Jeffrey Donovan, Jason Butler Harner, John Malkovich, Michael Kelly, and Amy Ryan, this beautifully-shot and hard-hitting drama is a great addition to Eastwood’s filmography.

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9 Letters From Iwo Jima (2006)

Told from the Japanese perspective, the war drama Letters from Iwo Jima chronicles the Battle of Iwo Jima through the eyes of Lieutenant General Tadamichi Kuribayashi, who was responsible for commanding a force of Japanese soldiers. Despite knowing the stakes, he leads his men to turn the island into a heavily fortified death trap and hold off American troops for as long as possible. The movie also focuses on young soldiers Saigo, Shimizu, and Baron Nishi, who make their last stand as the fight grows intense.

Letters from Iwo Jima Offers a Unique and Unflinching War Perspective

Boldly crafted and brutally real, Letters from Iwo Jima acknowledges the complex toll that the war took on both sides. Eastwood brought nuance and empathy to audiences by showing the enemy perspective. Certain scenes featuring Kuribayashi reflected on the leadership, compassion, and humanity shared by Japanese soldiers even when loss was imminent. The movie, as well as Eastwood’s masterful direction, earned a lot of praise as one of the best anti-war movies of all time.

8 Richard Jewell (2019)

Richard Jewell is an outstanding biographical drama based on a 1957 Vanity Fair article about the media and police’s mistreatment toward the titular individual. In the movie, Paul Walter Hauser stars as Richard Jewell, a security guard who discovers a mysterious backpack during the 1996 Summer Olympics in Atlanta and alerts the authorities about it. Initially hailed as a hero, when Jewell becomes the FBI’s prime suspect, he is vilified and an investigation follows.

Richard Jewell Is a Devastating Critique of Power and Control

In Richard Jewell, Eastwood tackles essential topics about issues surrounding law enforcement and media recklessness with an equal amount of care and sincerity. Hauser’s performance truly moved the audience because he embodied the wrongly targeted man with innocence and ordinary grace. While the acting and the direction are worth praising over and over again, the movie also sheds light on some causes that deserve wider attention, and with Richard Jewell, Eastwood left audiences questioning those in power.

7 The Mule (2018)

The Mule was a somewhat unusual project for Eastwood, as he returned to acting to play the lead role of Earl Stone, who was the subject of one of the most bizarre true stories set within the drug war to hit headlines in recent memory. At the age of 87, the former veteran and horticulturalist Leo Sharp (whose name was changed in the film to Stone) became a drug mule for a Mexican cartel and helped to smuggle merchandise over the border.

The Mule Is Eastwood’s Unique Directorial Effort

At over 80 years of age, Eastwood inserts a reflective element into the film that makes the film both funnier and more emotional as a result. Similar to Robert Redford’s recent performance in The Old Man & The Gun, Eastwood’s role as Stone served as an amalgamation of some of the various characters that he had portrayed throughout his career, and reminded his fans why they fell in love with him in the first place. Stone is forced to prioritize spending time with his family when he realizes how little time he has left.

6 American Sniper (2014)

American Sniper became a game-changing financial and cultural juggernaut that stands as one of Eastwood’s most commercially successful films ever. In an era dominated by superheroes and franchises, seeing an R-rated biographical film at the top of the box office for several weeks was a rarity. The movie unpacks the life of the controversial military veteran Chris Kyle (Cooper), whose marksmanship overseas earned him the reputation of being one of the deadliest killers in American history.

American Sniper Is a Game-Changing War Drama

Only a director like Eastwood and a performer of Bradley Cooper’s caliber were capable of making the project as successful as it was. He does a great job at showing Kyle’s complex relationship with patriotism, post-traumatic stress disorder, and his familial responsibilities, and offers a surprisingly balanced perspective considering that he has been outspoken in his politically conservative views. While American Sniper received a Best Picture nomination alongside many other accolades, Eastwood was sadly snubbed for Best Director.

5 Gran Torino (2008)

Gran Torino

Release Date
December 9, 2008

Cast
Clint Eastwood , Christopher Carley , Bee Vang , Ahney Her , Brian Haley , Geraldine Hughes

Gran Torino is a refreshingly earnest examination of generational hatred, cultural awareness, racism, and redemption. Eastwood stars as Walt Kowalski, a Korean War veteran who becomes a mentor to the young Hmong American teenager Thao Vang Lor (Bee Vang). It was the first mainstream film to spotlight the Hmong American experience. While Walt initially has a lot of bigoted beliefs that stem from his service in Korea, he learns about the challenges that Thao has faced and the violence that has impacted his community.

Gran Torino Portrays Social Change in a New Light

Anyone that has been a fan of Eastwood’s for a long time knows that he detests discrimination and xenophobia, so it was perfect for him to both direct and star in a film about modern race relations. Playing the quintessential gruff but big-hearted Vietnam vet felt real, lived-in, and easy for Eastwood, who proved the sensitive themes and an intimate character study can engage any audience. It’s a great film about the power of cultural respect that shows that even the most cold-hearted individual is capable of making extraordinary changes in their outlook.

4 Sully (2016)

Sully

Release Date
September 7, 2016

Sully recounts the incredible true story of Captain Sully Sullenberger (Tom Hanks), a U.S. commercial pilot who successfully landed a plane on the Hudson River on January 15, 2009, after a flock of seagulls forced him to make a crash landing. Following that, Sully and his experienced crew faced intense public scrutiny to determine if there really was no other way out of the situation. Incredibly, all of Sully’s passengers survived the event, and he has been hailed as a modern American hero ever since.

Sully Balances Tension and Crisis

Eastwood took an interesting approach to chronicling Sully’s life story. He explores his post-traumatic stress disorder and struggles to live up to the reputation of being a hero in a nonlinear story that does not revert to the types of clichés that are common in biopics. Hanks gives a very nuanced performance that perfectly fits Sully’s humble outlook and goals; he is unable to rest until he has ensured the safety of everyone on the flight. If there’s any Eastwood film in recent memory that deserves a serious critical reappraisal, it’s Sully.

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3 Invictus (2009)

Invictus is inspired by the incredible true story of South Africa’s World Cup victory in the wake of Nelson Mandela’s (Morgan Freeman) election as President. In 1995, the country held its first democratic elections and while Madela won the presidency, the nation was still divided. He sees the hugely popular sport of rugby as a means to unite South Africa’s many races. He supports the Springbrooks, a team that was not expected to perform well in the Rugby World Cup.

Invictus Is a True Story About Bridging Social Divides

Winning a bunch of awards and honors, Invictus resonated with the audience as an astounding tale of compassion, forgiveness and healing. Eastwood does a phenomenal job balancing the political tension within the context of an inspiring sports story by adding equal amounts of humor and warmth to the narrative. Matt Damon and Morgan Freeman deliver touching performances in their respective roles. Rather predictable, the movie is considered powerful for conveying something very profound, using sports as a metaphor for hope and potential.

2 Million Dollar Baby (2004)

Million Dollar Baby was the second Best Picture and Best Director win for Eastwood, who delivered one of the most heartbreaking sports movies ever made. He starred as Frankie Dunn, an ill-tempered, reclusive boxing trainer who takes on his first female student, Maggie Fitzgerald (Hillary Swank), only to become more attached to his protégé than he had ever imagined. Despite initial skepticism, once he witnesses Maggie’s perseverance and work ethic, Frankie pushes her to train harder.

Million Dollar Baby Is Eastwood at His Directorial Peak

Million Dollar Baby was a knock-out film that demonstrated why Eastwood is an auteur like no other. His empathetic lens, paired with a thoughtful cinematography, brought incredible depth to Swank’s character as she navigated both passion and prejudice. Gritty and inspirational, the movie focuses on life inside and outside the ring and the contrast is strikingly beautiful. Not only does it transcend clichés around sports dramas, but the movie also leaves an emotional impact on the viewer, and for that reason, it is one of Eastwood’s finest works.

1 Mystic River (2003)

Mystic River is one of the most nauseatingly intense crime thrillers of the 21st century. It tells the story of three lifelong friends, Jimmy, Dave, and Sean, who grew up together in Boston but went separate ways after experiencing a tragedy. Twenty-five years later, they are united as adults by another senseless tragedy, one that looks at the ugliness of abuse and the unrewarding nature of revenge.

Mystic River Is a Testament to Eastwood’s Many Gifts

A genuinely haunting tale that established Clint Eastwood as a director capable of producing the most tragic and unflinching stories about the human condition, Mystic River inspired all-time great performances from stars Sean Penn, Kevin Bacon, and Tim Robbins. The powerhouse actors brought subdued depth to the lingering wounds of their characters and made their present a reflection of their pasts. The movie carefully examines themes of guilt, grief, trauma, and revenge. It won several accolades, including Academy Awards and Critics’ Choice Awards for Sean Penn and Tim Robbins. Overall, it is a career-best achievement for everyone involved.



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