From The Outlaw Josey Wales (1976) to Million Dollar Baby (2004), here are the best Clint Eastwood-directed movies.
Few people in Hollywood can claim to have a career as accomplished and celebrated as Clint Eastwood. His work in spaghetti Westerns and crime thrillers and his endless array of badass dialogues have made him an icon in Hollywood. Even after attaining stardom, Clint Eastwood constantly reinvented himself. In the early 1970s, he made the transition as a director, and in the next five decades, surprised us with several prestigious projects. However, life hasn’t always been so kind to him. His journey remains a testament to one’s perseverance and hard work.
Born May 31, 1930, Eastwood spent his childhood in Depression-era California as his parents moved around to find jobs. After graduating from high school, he was drafted into the army where he spent two years before he switched to acting at 21. After much struggle, in the early 1950s, Clint Eastwood signed a contract with Universal Studios as a bit-player. Throughout the decade, he played simple characters in low-budget films. Fortunately, in the late 1950s, he got his big break with an important role in the Western TV series Rawhide (1959-1965).
Early in the 1960s, Clint Eastwood met Sergio Leone and went to Italy to shoot the unique spaghetti Westerns. His role as The Man With No Name in Sergio Leone’s Dollars Trilogy elevated him to international fame. Ever since, he’s been a part of some timeless films, both as an actor and director. Nothing beats watching the sneer and growl of Clint Eastwood on the big screen. Quickly then, here are all Clint Eastwood movies (directed) ranked.
All Clint Eastwood Movies Ranked
39. The Rookie (1990)
The Rookie was undoubtedly one of Clint Eastwood’s weakest projects as an actor and director. He wasn’t actually interested to begin with. Clint Eastwood agreed to make the film for Warner Bros. to let him pursue his passion project, White Hunter Black Heart. Eastwood was put in a spot when that film bombed at the box office, and he was left with a lackluster script for The Rookie.
The film was clearly a Lethal Weapon wannabe, where Eastwood plays the world-weary detective who is partnered with Charlie Sheen’s rich and rookie cop David Ackerman. Eastwood’s performance is just routine stuff, and the script is full of tiring clichés. The acting and direction are so bad at times that it feels like a parody of buddy cop dramas.
38. The 15:17 to Paris (2018)
Clint Eastwood has directed quite a few bad films in his five-decade directorial career. There are a few instances where a messy script derails his efficient direction. But only rarely have Clint Eastwood movies lacked professionalism on all fronts. The 15:17 to Paris is one such rare work in Eastwood’s career as a filmmaker. The film tells the true story of three young Americans who heroically confronted a terrorist while vacationing in Europe and stopped a terror attack.
Unfortunately, Eastwood’s first mistake is to cast the three men to portray themselves. This gimmick never works, and the script is unbelievably ham-fisted. Eastwood’s weak direction adds to the woes. The film fails to generate genuine drama despite the fact that the real-life incident is so fascinating.
37. Firefox (1982)
While in the 1960s, Clint Eastwood focused on mysterious Cowboy roles, and in the 70s, he was known as the tough cop, he attempted to diversify his choice of roles in the 80s. But that didn’t work out too well, as we ended up with this ‘okayish’ thriller starring Clint Eastwood as traumatised former pilot Michael Gant. The narrative deals with Cold War politics in the messiest and most awkward manner.
The flying sequences involving the titular Firefox were made with expensive special effects. However, everything about the film looks dated. Even Eastwood’s direction is uninspiring. The film can be seen as a relic of the Reagan era and doesn’t offer anything of value to entertain modern audiences.
36. Jersey Boys (2014)
For some reason, Eastwood seems mismatched to tell the story of this iconic rock group. Adapted from a Tony-award-winning musical play by Marshall Erickman and Rick Alice, Jersey Boys chronicles the story of four poor young men from New Jersey who come together to form the rock and pop band The Four Seasons in the 1960s. The straightforward narrative touches on their rise, fame, and their numerous troubles after finding success.
The narrative largely flows out in an inorganic and stiff manner. Of course, it’s well shot and acted, but the energy and humor inherent to the material doesn’t quite come together on screen. Perhaps this material needed a filmmaker like Baz Luhrmann (Moulin Rouge!) or Rob Marshall (Chicago).
35. Breezy (1973)
Breezy is the first Clint Eastwood directed flick where he didn’t act. It’s also a romance drama, which doesn’t have any dark psychological conflicts as in Play Misty for Me. Breezy revolves around a grumpy middle-aged real-estate salesman Frank Harmon (William Holden), who comes across a free-spirited, young hippie woman named Edith Breezerman, aka Breezy (Kay Lenz).
Their embarrassing, budding romance forms the crux of the story. Though not a typical Eastwood fare, the direction is pretty smooth, and he gets good performances from the actors. However, despite the non-exploitative nature of filmmaking, the whole scenario feels underdeveloped, especially due to the lack of strong characterizations. The film bombed at the box office. Nevertheless, it showed Eastwood’s skills in directing different narrative subjects.
34. Blood Work (2002)
Blood Work is just one of the many barely watchable Clint Eastwood movies that retain certain elements of Dirty Harry. Here, Eastwood plays celebrated FBI profiler, Terry McCaleb. He is after a serial killer, dubbed as the ‘Code Killer,’ because the killer leaves coded numbers as clues at each crime scene. When Terry comes close to catching the killer, he collapses of a heart attack.
Subsequently, he retires and gets a heart transplant a couple of years later. Random circumstances bring Terry to confront the serial-killer again. The film was written by L.A. Confidential scribe Brian Helgeland and is based on Michael Connelly’s novel. Nevertheless, this is a formulaic Eastwood fare with uninventive writing and average direction.
33. The Gauntlet (1977)
In The Gauntlet, Clint Eastwood plays a variation of a Dirty Harry-type tough cop. His Ben Shockley is an alcoholic and sexist guy who is tasked to go to Las Vegas and escort a witness named Gus Mally (Sondra Locke) to Phoenix. Gus Mally is a sex worker and a key witness in a mob trial. Therefore, both the mobsters and shady cops attempt to silence her. The Gauntlet is a fine escapist fare with some entertaining banter between Shockley and Mally.
Eastwood directs most of the over-the-top action sequences with flair and verve. The outrageous bus scene towards the end, despite its implausibility, puts a smile on our face. The script written by Dennis Shyrack and Michael Butler only relies on one-liners and shoot-outs to forward the narrative.
32. Hereafter (2010)
Clint Eastwood’s compelling phase as a director, starting from Mystic River (2003), hit a speed-breaker with Hereafter.Gran Torino, despite its controversial portrayal of Asian characters, had a tense, dramatic conflict at its center. Hereafter is a vague fantasy drama with no emotional resonance. The narrative has three storylines that eventually converge. In one, Matt Damon plays a traumatized psychic with a factory job.
Then a French reporter nearly gets killed during the 2004 Indian Ocean Tsunami. And, finally, there are young twin brothers, one of who gets tragically killed in an accident. What connects these three stories is that the individuals are haunted by death. The premise shows promise but doesn’t work because of the unexciting script and flat direction.
31. The Eiger Sanction (1975)
Eiger Sanction is a fairly entertaining Eastwood vehicle that’s let down by the underwhelming script. Clint Eastwood plays Dr. Jonathan Hemlock, a retired assassin and an art professor. The protagonist’s characterization and how Eastwood plays Hemlock gives it the vibe of a Bond film. Hemlock is forced to come out of retirement to find the identities of the men who killed his former colleague. The quest takes him to the Swiss Alps and a treacherous climb on the north face of Eiger Mountain.
Clint Eastwood himself did most of the dangerous stunts. He excels as both an actor and a director. However, the trio of screenwriters fails to develop the narrative’s dramatic aspects. And the film falls flat at crucial moments.
30. Sudden Impact (1983)
Sudden Impact was the fourth film in the Dirty Harry series and the franchise’s highest-grossing film. The critical response was, however, mixed. In Sudden Impact, the culprit Harry Callahan pursues vigilante killer Jennifer Spencer (Sondra Locke). She is seeking revenge on the individuals who raped her and her teenage sister, who is still in a vegetative state. Harry tries to nab the killer while also putting up with the hostile locals and a disdainful police chief (Pat Hingle).
Though the film opens with a mysterious premise, the identity of the killer and motive is revealed too soon. Moreover, Sondra Locke wasn’t the right choice to play the traumatized and stoic vigilante. Clint Eastwood moves the narrative with an action-packed direction. Yet the superfluous nature of the storyline is a downer.
29. Cry Macho (2021)
At the ripe age of 91, Clint Eastwood had done a wonderful job of acting and directing himself. But Cry Macho, on the whole, doesn’t tug at our heartstrings as it was intended to. Eastwood reunites with his Gran Torino and The Mulescreenwriter Nick Schenk. He once again plays a growling old man involved in a personal mission to redeem himself. Racial epithets are casually thrown, and of course, Clint Eastwood hardly cares about being politically correct.
The story revolves around a former rodeo star Mike Milo. His former employer hires him to travel to Mexico and bring back his teenage son, Rafo. After making the trip, Milo understands his former employer’s real reasons to kidnap his son. At the same time, Milo forms an unlikely friendship with Rafo.
28. Absolute Power (1997)
Absolute Power is a mediocre Clint Eastwood vehicle despite featuring Hollywood A-listers. The script was written by author and screenwriting genius William Goldman. Jack N. Green, who crafted the gorgeous visuals in Unforgiven & A Perfect World, is the cinematographer. Clint Eastwood reunites with his Unforgiven co-star Gene Hackman, and other talented actors are in the cast, including Ed Harris, Judy Davis, and Laura Linney.
Yet Absolute Power suffers due to an underwhelming storyline. Eastwood plays a world-class cat burglar named Luther Whitney. While breaking into an elite mansion in the DC area, he witnesses a murder directly connected to America’s most powerful person. What follows is a clichéd action thriller that also lacks craftsmanship.
27. Midnight in the Garden of Good and Evil (1997)
Clint Eastwood’s interest in choosing diversified directorial projects continued with this adaptation of John Berendt’s renowned novel. Midnight in the Garden of Good and Evil is a quirky high-society melodrama that’s underwhelming at times. Set in Savannah, Georgia, the film opens with a New York writer, John Kelso (John Cusack), arriving at the city to write a story about the much-talked-about Christmas Party of super-rich Jim Williams (Kevin Spacey).
But soon, the Christmas bash turns into a night of crime as Jim stands accused of murder, and his gay identity comes under spotlight. John covers the rich man’s trial, wondering if there’s material to make a book out of it. The engaging performances and the rich setting make this one of Eastwood’s decent directorial works.
26. Space Cowboys (2000)
Space Cowboys tells a familiar tale of rivalry, friendship, and bickering between old men. The only change in the set-up is that they happen to be astronauts and embark on a dangerous space mission. Eastwood’s revived career post the critical and commercial hit of Unforgiven gradually waned by the time he reached 70 in 2000. In fact, when Space Cowboys was in production, there were rumors that it would be his last project. Fortunately for us and for him, he didn’t retire with such a mediocre drama.
The film largely works due to the solid cast, which includes Tommy Lee Jones, James Garner, Donald Sutherland, and Eastwood. Despite the novelty of the premise, the second half only turns more routine and dull.
25. White Hunter Black Heart (1990)
Eastwood’s star actor persona was gradually fading in the late-1980s. He made his last Dirty Harry film, The Dead Pool,in 1988. In 1990, he turned 60 and began a new phase in his career, taking up varied projects as a filmmaker. He was interested in bringing to screen Peter Viertel’s 1953 book. The book offered a dramatized take on legendary filmmaker John Huston’s adventures in Africa during the shooting of The African Queen (1951). Clint Eastwood himself played the egocentric central character named John Wilson.
Despite being an atypical Eastwood fare, the film was largely ignored due to clumsy and dull writing. It turned out to be one of the biggest box-office disasters in the filmmaker’s career.
24. True Crime (1999)
True Crime is a familiar yet riveting moral drama anchored by Eastwood’s steadfast direction and captivating performances. Clint Eastwood plays Steve Everett, a journalist, and a recovering alcoholic. He hates playing by the rules. One day, he is assigned a human interest story that involves interviewing a Black Death row inmate Frank Beechum. Beechum continues to claim that he is innocent. Soon, Everett gets interested in investigating the flaws in the case. When Everett is convinced of Beechum’s innocence, he races against time to save him.
Though this is a predictable tale of a cranky Eastwood character attempting to redeem himself, Eastwood, the director, creates enough dramatic intrigue to keep us emotionally invested. Everett’s meeting with Beechum is one of the film’s most brilliantly staged and well-performed sequences.
23. Heartbreak Ridge (1986)
Heartbreak Ridge is a clichéd drama about a flawed combat veteran seeking redemption. Clint Eastwood himself plays the grizzled, Gunnery sergeant Thomas Highway. The hard-drinking veteran is nearing retirement and gets transferred to his old unit, where he is tasked with training an unfit platoon of slackers. Thomas clashes with the new Major in the job. On the personal front, he tries to reconcile with his ex-wife Aggie.
The script is so predictable, and the conflicts are set as well as resolved in a neat manner. It relies too much on the time-worn tropes of military training narratives. Even Eastwood’s direction feels inadequate. But what makes Heartbreak Ridge watchable is the veteran actor’s intense and comedic performance as a misanthropic individual.
22. J.Edgar (2011)
Audiences and critics alike were intrigued when the 80-year-old Clint Eastwood was involved in making the biopic of J Edgar Hoover. And there was much anticipation with an A-list actor like Leonardo DiCaprio associated with the project. But the semi-fictionalized portrait was a mess due to the lackluster two-dimensional script. Hoover, who led the FBI for nearly half a century (1924-1972), was considered a highly controversial figure.
In fact, horrific truths about Hoover’s actions during the Civil Rights era have surfaced in the last decade or so. DiCaprio’s Edgar is not a likable figure in the film. But that’s not the problem. It lacks a deep understanding of this complex and ruthless political figure. Eastwood and DiCaprio’s commitment fails to save us from the flat narrative.
21. The Mule (2018)
Clint Eastwood was rumored to have retired from acting quite a few times. After the 2012 movie Trouble with the Curve,he seemed done. But after Gran Torino (2008), Eastwood directed himself again in The Mule, a decent drama based on a real-life incident. The then 88-year-old Clint Eastwood played 90-year-old Earl Stone, who is a horticulturist and a Korean War vet.
Due to financial and personal woes, Stone becomes a mule, delivering cargo for a Mexican drug cartel. After a few successful runs, Earl Stone comes under the radar of DEA agents. Despite quite a few clichéd turns, Mule largely works due to Eastwood’s even-handed direction. Clearly, the filmmaker/actor isn’t subtle with his political commentary.
20. American Sniper (2014)
American Sniper is somewhat of a return to form for Clint Eastwood after quite a few duds like Hereafter and Jersey Boys. The film was nominated for six Oscars and became a box-office hit. It is based on the real-life story of Navy SEAL sniper Chris Kyle. Bradley Cooper plays Kyle, who is touted as the most deadly sniper in the history of the United States military. Kyle has served four tours in Iraq and is said to have saved countless American lives due to his ‘pinpoint accuracy.’
The film explores the man’s life on and off the battlefield and the trauma he endured until he was murdered in 2013. Clint Eastwood makes a gripping drama out of Kyle’s life. But at times, it becomes an unabashed celebration of his legacy rather than deeply examining his PTSD.
19. Richard Jewell (2019)
Richard Jewell tells the true story of a falsely accused man who was vilified and destroyed by the media. In Atlanta’s Centennial Park on July 27, 1996, Richard Jewell – an obese middle-aged security guard – accidentally came across a backpack full of pipe bombs and saved the lives of countless civilians. Initially, the media and the public hailed him as a hero. But when the FBI leaked information that Richard was also a suspect, the journalists commenced a witch-hunt.
Richard’s mental health issues from the past are put together to create a distorted view of him as an attention-seeking bomber. Clint Eastwood offers a well-dramatized sympathetic portrait of Richard’s struggles to prove his innocence. Paul Walter Hauser is phenomenal in the titular role.
18. Bronco Billy (1980)
Bronco Billy was a charming, gentle drama about a modern-day Cowboy. Clint Eastwood plays the eponymous character, an ex-convict and an ex-shoe salesman who spearheads a traveling Wild West Show. His crew consists of people like himself: ex-convicts, misfits, and wannabe cowboys. Billy’s troupe gets a new arrival in the form of a spoiled, wealthy heiress named Antoinette Lily. Sondra Locke plays Lily, who previously paired with Eastwood in Gauntlet.
Bronco Billy is about a dreamer following the old codes of the West in an increasingly bleak modern world. This was Eastwood’s favorite among the films he directed. The film’s producer Dennis Hackin wrote the screenplay. The film never becomes a top-tier Eastwood feature because of awkward execution in certain places and shallow writing.
17. Flags of our Fathers (2006)
After the grand success of Million Dollar Baby, Clint Eastwood moved to do an obscure passion project. He wanted to make a two-part film on a little-known period in the Pacific War. The first film, Flags of Our Father, delves into the story behind the most familiar picture of WWII. It shows six American servicemen raising their flag at Mount Suribachi in Iwo Jima. While the media and politicians portray this as a testament to their soldiers’ heroism and valor, the truth behind the picture offers a thought-provoking perception of the battlefield.
Eastwood smartly uses monochrome and color to recreate the gritty atmosphere. Moreover, his portrayal of battlefield violence isn’t gratuitous. However, the film’s flawed narrative structure avoids deep reflection on the subject.
16. Bird (1988)
Clint Eastwood’s Bird was an ambitious, underseen biopic of jazz legend Charlie ‘Bird’ Parker. His graceful direction perfectly sets the tone of the film. This was only the second film directed by Eastwood that he didn’t act in. The titular character was heartbreakingly played by Forest Whitaker. Writer Joel Oliansky’s script covers the turbulent phase in Parker’s life who suffered mental health issues and addiction problems before he passed away at 34.
Clint Eastwood is a jazz fan, and Bird is supposedly his labor of love. While his nuanced direction was lauded, Eastwood’s approach to not focus on the social forces surrounding Charlie Parker was questioned. Bird is more of a mood-piece, and Eastwood barely delves into the man’s life.
15. Honkytonk Man (1982)
Honkytonk Man was a beautiful road movie where Eastwood sheds off his tough-guy persona and plays a sensitive country singer. The film was based on the novel by Clancy Carlile, who also adapted it into a script. Set during the Great Depression era, the narrative revolves around Red Stovall, an unsuccessful singer with tuberculosis. He receives an invitation to audition at Grand Ole Opry, a famous country music concert in Nashville. On his way to the concert, Redvisits his sister and picks up her talented teenage son, Whit.
Clint Eastwood cast his son Kyle Eastwood as Red’s nephew Whit. Though the film is built on a sentimental premise, it’s to Eastwood’s credit as a director and actor that the film isn’t lost to melodrama.
14. The Bridges of Madison County (1995)
The Bridges of Madison County is a polarizing romantic drama that some might find heartwarming while others, annoyingly dull. It is an adaptation of Robert James Waller’s melodramatic bestseller. With a run time of 135 minutes, Clint Eastwood makes a great effort to conjure a nuanced drama out of a predictable narrative. Set in the summer of 1965, Meryl Streep plays Francesca, a terribly bored middle-aged housewife with two children.
While Francesca’s husband and kids spend four days away from home, she accidentally meets Robert Kincaid (Eastwood), a National Geographic photographer. They eventually fall in love, and the four days have a lasting impact on their lives. The stunning countryside landscape perfectly complements Eastwood’s subtle staging of the love story.
13. Pale Rider (1985)
Written by The Gauntlet screen-writing duo Dennis Shyrack-Michael Butler, Pale Rider marks Clint Eastwood’s return to the Old West after The Outlaw Josey Wales (1976). The narrative is set in a small mining community near a Northern California creek. A mysterious drifter, also a preacher (Eastwood), reaches the town to help the people getting harassed by the thugs of a businessman. This familiar, straightforward Western drama is elevated by a good ensemble cast and well-rounded performances.
Michael Moriarty is particularly good as the local miner Hull Barrett. Despite the predictable nature of the script, Clint Eastwood’s careful compositions bring a haunting and tense tone to the proceedings. However, Eastwood excels more as an actor than a director.
12. Gran Torino (2008)
Gran Torino has a conventional narrative arc, packed with appalling racial stereotypes. Clint Eastwood, as usual, plays the cantankerous old guy named Walt Kowalski. A Korean War vet, he worked in Ford until his retirement. He’s lost his wife recently, and isn’t connected with his kids. Walt now spends his day cherishing his 1972 Gran Torino while drinking beer on his porch.
He’s among the few white guys in a neighborhood inhabited mostly by Hmong people. He despises change, but the grumpy, old-fashioned man is forced to confront his prejudices when he forms an unlikely bond with his Hmong neighbors. Gran Torino has its share of heart-warming moments. But its racist vocabulary and stereotyping are problematic.
11. Play Misty for Me (1971)
The Year 1971 was a significant one in Clint Eastwood’s film career. It was the year he collaborated with his friend-and-mentor Don Siegel to make the blockbuster hit Dirty Harry. The film launched a franchise and influenced many cop dramas and thrillers of the era. The duo also made The Beguiled, a Gothic Civil War drama, which was a box-office flop but gained a cult status in the later years.
But the undoubtedly courageous decision of the year is Clint Eastwood taking up the directorial reins of the psychological thriller Play Misty For Me. He also played the central character, which is far different from his usual Western macho hero. The perseverance of the legend is evident in the fact that he was directing films fifty years later (Cry Macho in 2021) amidst the COVID-19 Pandemic.
10. Invictus (2009)
Clint Eastwood’s Invictus portrays Nelson Mandela’s struggles in bringing together South Africa after Apartheid. It opens in 1990 when Mandela was released after 27 years of prison life, and the country appeared to be on the verge of a Civil War. However, Mandela gradually rebuilt the nation and saw sports as one of the unifying forces.
Eastwood’s measured, low-key direction shows how Mandela (Morgan Freeman) cleverly used the Rugby World Cup, held in South Africa, to reconcile the wounds of the past. Eastwood’s patient approach is his greatest strength, and in Invictus, he gradually reaches the high emotional points without rushing them. Besides, he gracefully handles the many subplots in the narrative. Eventually, what’s unforgettable about the film is Morgan Freeman’s phenomenal performance as Mandela.
9. High Plains Drifter (1973)
Apart from John Ford and John Wayne, Clint Eastwood was the icon closely associated with the Western genre. Eastwood played several uncredited, bit parts in films in the 1950s before getting the lead role in Leone’s spaghetti Westerns. So it’s no wonder that Eastwood would naturally direct himself in a Western. The actor/director is often reductively described as ‘workmanlike’ and ‘conservative.’
But his craftsmanship is no less than the finest American filmmakers. And High Plains Drifter is one of Eastwood’s most daring and revisionist Western flicks. He plays an anti-hero with no name. For unknown reasons, the enigmatic stranger arrives at a mining town and helps the townspeople defend themselves from three dangerous outlaws. It’s a bloody and bleak Western made for the Vietnam War era.
8. Sully (2016)
Sully is the perfect all-American, non-controversial drama that appeals to a wide range of audience. The same couldn’t be said about Eastwood’s previous polarizing film American Sniper. Few critics even called it his best work after Letters from Iwo Jima. Sully, of course, isn’t mounted on such a lofty scale. Nevertheless, it’s an incredibly effective drama, spearheaded by a grounded performance from the ever-dependable Tom Hanks.
The film tells the story of airline pilot Chesley Sullenberger, who became a hero overnight after successfully landing a completely damaged plane on the Hudson River, saving 159 lives. But his decision to make such a dangerous landing is questioned. What follows is a riveting investigation that proves beyond doubt the soundness of the veteran pilot’s judgment.
7. Changeling (2008)
Clint Eastwood’s streak as the astonishing septuagenarian filmmaker continued with the depression-era crime dramaChangeling. Based on a true incident, Michael Straczynski’s script follows a single mother’s quest to find her missing boy. Angelina Jolie plays Christine Collins, who lives in 1928 LA with her nine-year-old son Walter. She returns home from work one day and can’t find her child. Five months later, Christine receives news that her boy has been found. Alas, she reaches the station only to see that it’s not Walter.
A devastating series of events follow this discovery, and Christine is subjected to great suffering by the system. Changeling is a brilliantly performed period drama where Eastwood gracefully stages the narrative’s emotional high points. There’s no flashy camerawork here, and he shifts between tones with astounding skill.
6. A Perfect World (1993)
Clint Eastwood returns to the road movie genre (after Honkytonk Man) with A Perfect World, which is also mixed with elements of crime. Set in rural Texas in 1963, the film revolves around escaped prisoner Butch Haynes (Kevin Costner). Butch takes an 8-year-old Philip Perry hostage. The boy is raised by his deeply religious mother. On the road, as Butch and Philip embark on a cross-country journey, they bond like father and son.
However, Butch is pursued by Texas Ranger Red Garnett (Eastwood) and criminologist Sally Gerber (Laura Dern). Despite being fairly predictable, A Perfect World largely works due to the well-rounded cast and Eastwood’s sharp direction. He turns a simple manhunt narrative into a thoughtful, character-driven drama.
5. The Outlaw Josey Wales (1976)
The Outlaw Josey Wales is one of the Western genre’s finest films, though overlooked sometimes due to the popularity of the Dollars Trilogy. Eastwood directs and stars as Josey Wales, a Missouri farmer who is driven to revenge by the murder of his wife and young son by a band of Union militants during the American Civil War. He joins a Confederate guerrilla band and fights in the Civil War. However, due to the Union’s victory, all his brothers-in-arms are forced to surrender, while Eastwood (typically) remains an outlaw and is hunted down by the Union.
Despite the film being about a farmer taking part in the Civil War, Eastwood remarked that it was an anti-war film in an interview with WSJ: “As for Josey Wales, I saw the parallels to modern day at that time. Everybody gets tired of it, but it never ends. War is a horrible thing, but it’s also a unifier of countries… Man becomes his most creative during the war. Look at the amount of weaponry made in four short years of World War II — the number of ships, guns, tanks, inventions, planes, P-38s and P-51s, and just the urgency and the camaraderie and the unifying. But that’s kind of a sad statement on mankind if that’s what it takes.”
4. Mystic River (2003)
Eastwood’s best phase as a filmmaker begins with Mystic River, an adaptation of Dennis Lehane’s novel. It was only his third directorial (after Breezy & Bird) where he didn’t act. Mystic River is a star-studded, character-driven whodunit that offers a distressing and intriguing experience. Brian Helgeland’s riveting adapted script was masterfully staged by Eastwood. The narrative revolves around three friends from Boston.
It opens when they are 11 years old. One day, while playing on a sidewalk, a stranger who identifies himself as a plain-clothed cop orders one of the boys to get into his car. What follows, haunts the lives of the three individuals even 25 years later. Eastwood extracted solid performances from Sean Penn and Tim Robbins, both of whom won Oscars.
3. Letters from Iwo Jima (2006)
While Flags of Our Fathers told the tale of the Battle of Iwo Jima from the US soldiers’ point of view, the companion piece, Letters from Iwo Jima, addresses the same events from the Japanese perception. Clint Eastwood worked with Japanese screenwriter Ira Yamashita and talented Japanese actors, spearheaded by the phenomenal Ken Watanabe. Letters from Iwo Jima is not only a far better film than Flags of Our Fathers, but it’s also one of Eastwood’s greatest achievements as a filmmaker.
His compositions are haunting and perfectly complement the slow-burn narrative. The sense of foreboding he builds up in the first half speaks of the legend’s artistic talent. Tom Stern’s cinematography improves on the bleak, faded look employed by Janusz Kaminski in Saving Private Ryan (1998).
2. Million Dollar Baby (2004)
Million Dollar Baby proved Eastwood could pack both emotion and action in a film. Maggie Fitzgerald, played by Hilary Swank, is an aspiring boxer who turns to Eastwood’s Frankie Dunn to train her. The two form a formidable but unlikely duo, where Eastwood keeps a steely watch on his protege, avoiding any sort of a father-daughter relationship between them. Nevertheless, fate ruins Maggie‘s life, and Frankie is forced to commit an act of mercy and love. Eastwood and Swank are accompanied by Morgan Freeman, who plays Frankie Dunn‘s gym assistant. Freeman delivered a great performance, earning him his first and only Academy Award.
Million Dollar Baby scooped up numerous Academy Award nominations and wins, notably Freeman for Best Supporting Actor, Swank for Best Actress, Clint Eastwood for Best Director, along with Best Picture. It really proved to be a KO victory for Clint Eastwood.
1. Unforgiven (1992)
David Webb Peoples wrote the script for Unforgiven in the 1970s, long before he worked on the scripts of cult sci-fi classics Blade Runner (1982) and Twelve Monkeys (1995). Eastwood bought the script in the 1980s but only started working on it after a string of mediocre hits and big flops. And Unforgiven actually revived his career as an actor and director, bringing Eastwood two Oscars. It’s considered as one of the greatest Westerns ever made.
The spectacularly shot film was set in the 1880s Old West and revolves around a retired gunslinger Bill Munny(Eastwood). A vicious act of violence pits Bill against a sadistic, authoritarian sheriff (Gene Hackman). Morgan Freeman also plays an important supporting role. Eastwood’s astounding directorial vision offers an unromanticized perception of the Old West, which influenced many Western genre films in the following decades.
Clint Eastwood is one of Old Hollywood’s few living icons and trailblazers. Before he got into acting, Eastwood auditioned for a whole year without any success. Yet he kept trying and only became an established actor at least a decade after his screen debut. Now Clint Eastwood is also considered one of the best American filmmakers. Though he isn’t currently working on a project, Clint Eastwood has made it clear that he has plans to retire.
Let’s wait and see what exciting projects he makes in his 90s, and perhaps, like the great Portuguese filmmaker Manoel de Oliveira (1908-2015), he’ll keep directing films even after he turns 100.
(Additional writing by Aditya Sarma)