Who he wants to be: The 20 best films directed by Clint Eastwood, ranked

Based on Robert James Waller's wildly successful novel, "The Bridges of Madison County" is a romantic tale of a photographer (Eastwood) who enters a brief yet torrid affair with a bored and neglected housewife (Meryl Streep) that will change their lives forever and leave a legacy to be found by the housewife's children that also change theirs. It's a depiction of a late-life romance that is far better than it deserves to be, even if it's not as good as the book itself.

Taking his signature gruff exterior out of Westerns and cop movies, Eastwood stars and directs in this story of a Marine sergeant who is tasked with getting a bunch of lackluster recruits whipped into shape for what would be the 1983 invasion of Grenada. Much of "Heartbreak Ridge" feels like B-Movie material, but Eastwood treats the subject matter with the due amount of respect, making it a film that hums along at its own pace, delivering a fairly satisfying experience overall.

So much of "Bronco Billy" feels like an elegiac look at the romanticism of the Old West, wrapped in a sense of finality as the dramedy follows a broken-down Wild West circus as it drifts from town to town, with its leader (Eastwood) inadvertently stealing a bride (Sondra Locke) while trying to get a permit. A box-office failure in 1980, modern audiences seem to have a greater appreciation for the film today, one that was generally shared by critics at the time. Maybe people weren't ready for a self-effacing Eastwood outside of his "monkey movies," but "Bronco Billy" stands as an affable and respectable entry in his filmography.

"White Hunter, Black Heart" is a thinly veiled, fictional take on the experiences of director John Huston and his crew during the filming of "The African Queen" in the 1950s. Director John Wilson (Eastwood) is obsessed with big game hunting, possibly more so than completing work on his upcoming film. Eastwood successfully looks at the concept of toxic masculinity long before it was ever a millennial buzzword, as he masterfully delivers a commentary on the fragility of the male ego wrapped in the general insecurities of artists, particularly filmmakers.

Morgan Freeman stars as Nelson Mandela in his third collaboration with Eastwood in this depiction of real-life events surrounding the 1995 Rugby World Cup. Matt Damon stars as South African National Team captain Francois Pienaar, who leads his team under the watchful eye of Mandela, who is on the national stage for the first time as president of South Africa, leading a nation still fresh from the specter of Apartheid. The two men share a similar burden, as both know the value of a South African championship and how it will bode for the country they love.

Tom Hanks does that thing he does in his first collaboration with Eastwood in the true-life tale of Captain Chesley Sullenberger, an airline pilot who miraculously saved 155 passengers and crew when US Airways Flight 1549 crash-landed in the Hudson River in January 2009. Hanks plays Sullenberger with all the affable charm you expect him to, and Eastwood frames the proceedings in an equally reliable fashion that stands as a subtle tribute to a modern-day hero.

*While Richard Tuggle is credited as director, Eastwood replaced him early on in filming.

Eastwood successfully deviates from his Harry Callahan cop persona to direct and star in a different tale of a cop whose sexual proclivities are on a collision course with a murder investigation he's working. Certainly ahead of its time, "Tightrope" succeeds in telling a story where the stereotypical hard-nosed detective actually grows, and in this case, learns to respect women, particularly when his primary dealings, outside of with his daughters, have been with sex workers. 

This is a somber yet not-quite-elegiac tale of Red Stovall (Eastwood), a hard-living musician who gets one last chance to prove himself on the biggest stage: the Grand Ole Opry in Nashville, Tennessee. Despite his health declining as a result of tuberculosis mixed with alcoholism, Stovall is determined to push on, dragging his nephew (Kyle Eastwood) on one last adventure that finds the two wading through brothels and talent scouts to get Red on stage before it's too late. The film is a gentle but effective effort from Eastwood.

The first of two companion films showing the immediate effects of the Pacific campaign during WWII, "Flags of Our Fathers" focuses on the group of soldiers made famous by the raising of the American flag at Iwo Jima in the wake of what was a major victory. As the soldiers are allowed to go home to serve as ambassadors and spokespersons for war bonds, they bring home with them the horrors of war and a sense that their newfound celebrity is undeserved as their fellow soldiers continue to fight and die overseas. Adam Beach stands out as the tragic Corporal Ira Hayes, a Native American who succumbs to the pressures of being a ready-made hero, as he feels guilt and discrimination from his fellow (white) Americans.

Eastwood's directorial debut is a simple yet effective potboiler about a popular evening DJ who gains a fan (Jessica Walter) who becomes more than a little obsessed after what was supposed to be a brief fling. Little does the DJ know, his fan isn't one to take no for an answer, something that quickly turns deadly as he tries to save himself and his new love from the unhinged former flame.

A companion film of sorts for 1973's "High Plains Drifter," Eastwood saddles up as "The Preacher," a mysterious man of the cloth who drifts into a snowy mining town, where the residents are under the thumb of mining baron Coy LaHood (Richard Dysart). Befriending a lowly miner (Michael Moriarty) and his family, the Preacher battles LaHood's men, bringing justice and a sense that a higher power truly watches over the oppressed.

Playing off themes presented in Sergio Leone's "Dollars" trilogy, "High Plains Drifter" goes an extra step, taking the motif of the "Man With No Name" and spinning a tale that feels almost supernatural in nature. Eastwood directs and stars as "The Stranger," a man with no identity who drifts into a town on the brink of violent collapse. He's begged by the townsfolk to save them, but this is a town with a dark past and a connection to "The Stranger" that may be even darker. Highly controversial for a rape scene that some consider needless, "High Plains Drifter" is as much horror film as Western but every bit as watchable either way.

Jazz aficionado Eastwood makes a bold attempt at chronicling the life of saxophonist extraordinaire Charlie Parker (Forest Whitaker) in "Bird." Eastwood chooses to tell Parker's story as a set of vignettes as opposed to a straightforward narrative, shifting back and forth through key points in his life and showing his mastery of the genre alongside his crippling heroin addiction. Relationships with fellow groundbreaking artists like Dizzy Gillespie and Red Rodney as well as his wife Chan are featured to bring some sense to the meteoric rise and fall of a jazz titan.

In what feels like the final chapter (if not in name) to the Dirty Harry saga, "Gran Torino" is the story of a Walt Kowalski (Eastwood), a crotchety bigot who has to lay down his personal prejudices (and defenses) to come to the aid of a young Hmong boy (Bee Vang) pressured into stealing the old man's vaunted Gran Torino. Eastwood weaves a somber tale marked with equal parts hope and tragedy as Kowalski grows closer to his adopted family to the point that he has to risk it all to save them in a way he never thought he would.

Without question, "The Outlaw Josey Wales" is easily Eastwood's second-best Western. Unlike previous and future efforts "High Plains Drifter" and "Pale Rider," the point is not to position Eastwood as a vengeful savior but rather as a man who's driven by revenge and also by his humanity. While he seeks to be alone in the wake of the death of both his original family and his surrogate family of marauders during the tail end of the Civil War, Wales manages to build yet another family, one full of outcasts and left-behinds, who prove to be his strongest — one in search of ultimate peace even if it comes at the end of a gun barrel.

The first film since 1959's "Ben-Hur" to win Oscars for Best Actor and Best Supporting Actor, "Mystic River" is a haunting tale based on Dennis Lehane's best seller about three lifelong friends whose past and present collide with deadly consequences. Sean Penn, Kevin Bacon and Tim Robbins are magnificent as the friends whose burdens and secrets prove too much to maintain the loyalty they built since childhood.

Eastwood collected his second Best Picture and Director Oscars for this tale of a female boxer (Hilary Swank) whose meteoric rise in the ring was met with a crashing and disastrous fall. "Million Dollar Baby" is more about how even the hardest men deal with tragedy and how some requests can often be far too difficult to grant. Morgan Freeman returns as a supporting actor to Eastwood's lead, serving in a similar fashion as a conscience to Eastwood's grizzled boxing manager.

The companion film to "Flags of Our Fathers," "Letters from Iwo Jima" is by far the superior, if not more ambitious of the pair. Filmed mostly in Japanese, the film stars Ken Watanabe as a commander of Japanese soldiers on the island of Iwo Jima in 1994. "Letters" is a film that shows viewers the perspective of the Japanese, humanizing them and trying to give insight into how war and honor mix under extreme pressure. While "Flags" focused on the aftermath of the battle and its effect on the celebrated U.S. soldiers, "Letters" takes us into the heart of defeat with a sense of dignity and pride not usually shared when dealing with an "enemy" force.

This film, quietly released in the wake of the massive Oscar haul of "Unforgiven," threatened to be the top film on our list. While nowhere near as epic as "Unforgiven," "A Perfect World" makes up for it in pure heart. Set in the 1950s, a pair of convicts stage a daring escape, with one of them, Butch (Kevin Costner) developing a unique relationship with a boy hostage who he looks at more as a partner in crime than a prisoner. On his trail is a world-weary Texas Ranger (Eastwood) and a sociologist (Laura Dern), who learn Butch is much more than he seems even though their first priority is saving the child. This leads to a climax that won't leave a dry eye in the house.

The crown jewel of Eastwood's career and his final Western to date, "Unforgiven" is the tale of an aged gunfighter turned rancher who is tasked with one more fight: facing off against an affable but equally deadly sheriff (Gene Hackman) in a battle of wits and bullets, serving as a final commentary on the brutality of gunslingers against the manufactured myths that romanticize them. The Best Picture-winning film features a strong supporting cast, including Morgan Freeman, Frances Fisher and Richard Harris.