The Couch Potato's Guide to Old and New Hollywood: The Legacy of Clint Eastwood

By Geoff Carter

Clint Eastwood has been a screen icon for the past sixty-six years. He’s acted in over seventy-two films, directed forty-five, and produced more than fifty, sometimes wearing all three hats during a single project. He has been responsible for such award-winning classics as Million Dollar Baby, Unforgiven, and Letters from Iwo Jima. Although he has one of the most recognizable faces in the world, Eastwood’s screen personas—along with his directing style—are typically quiet, understated, and as uncomplicated as the family dog—even though he might look as tightly wound as a guitar string onscreen.

His career began in the mid-fifties when he appeared in such classics as Tarantula and Return of the Creature before establishing himself as a steely-eyed Western hero in 1964’s A Fistful of Dollars. Eastwood’s first directing foray was 1971’s Play Misty For Me and was followed by dozens more, including Bronco Billy, A Perfect World, and The Bridges of Madison County.

Eastwood’s career underwent something of a renaissance in his later years. Starting with the award-winning Unforgiven in 1992—when he was 62 years old—the venerable director acted in and directed such critical successes as Million Dollar Baby, Gran Torino, The Mule, and Cry Macho—his newest, all films in which he plays crusty old men seeking redemption (and perhaps forgiveness) for past transgressions. He appeared—and appears—at 91 years of age, to be at the top of his game both in front of and behind the camera. His films Million Dollar Baby and Unforgiven won Best Picture and Best Director Academy Awards and his films are now consistently recognized as some of the best in the business.

Eastwood in neither a showy actor nor a stylish director. His stories are told in a simple, straightforward, and honest style; while the characters he plays have experienced layers of history, nuance, and scar tissue, those attributes simmer hidden below the surface of his cool steely-eyed glare. His characters, and his films, have grown less macho and more layered in his later years. Frankie Dunn or Will Munny or Walt Kowalski are strong assertive men, but Eastwood has filled in their interior selves with quiet, experienced, and sometimes wounded sensibilities. He has aged gracefully—and so have his characters.

They aren’t heroes anymore, they’re just people. So, without further ado, here are the top ten films both directed by and starring Clint Eastwood.

The Top Ten Films of Clint Eastwood

Unforgiven: Will Munny (Eastwood) a pig farmer who is a retired gunslinger is reluctantly recruited by The Schofield Kid to get the bounty on two cowboys who cut up a prostitute in the town of Big Whiskey. Will recruits his friend Ned (Morgan Freeman) to accompany them, but once they get to the town, Munny is severely beaten by the sheriff Little Bill (Gene Hackman). He recovers and the group goes on their mission. After Ned is caught by Little Bill, Will takes the law into his own hands—with a vengeance. Eastwood’s portrayal of Munny is an understated masterpiece; the audience—and his cohort—never suspect the ruthlessness and real violence (and justice) inside him. Notable for Gene Hackman’s performance as the sadistic sheriff.

Starring: Clint Eastwood, Gene Hackman, Morgan Freeman, Jaimz Woolvett, Saul Rubinek, Richard Harris, and Frances Fisher. Written and directed by Clint Eastwood.

Million Dollar Baby: Frankie Dunn (Eastwood), a trainer and owner of a gym is asked by Maggie (Hilary Swank), a waitress from the Ozarks, to be her coach. Stating he doesn’t train girls, Frankie refuses until he is ultimately persuaded by Maggie’s grit and the arguments of his only employee—and friend, Scrap (Morgan Freeman). After he takes her on, Maggie’s career takes off. She knocks out everyone she faces and eventually, in spite of Frankie’s trepidation, he schedules a title for her with disastrous results. Frankie Dunn, like many of Eastwood’s characters, only eventually allows his true feeling for Maggie—and the depths of his devotion—to rise past his crusty and acerbic exterior. Notable for the outstanding supporting performances by Hilary Swank and Morgan Freeman.

Starring: Clint Eastwood, Hilary Swank, Morgan Freeman, Jay Baruchel, Mike Colter, and Margo Martindale. Written by Mike Figgis and Francis X. O’Toole. Directed by Clint Eastwood.

Gran Torino: Walt Kowalski (Eastwood), a newly widowed UAW retiree hangs onto his house—all he has left—in a rapidly deteriorating Detroit neighborhood. While chasing gang bangers off his property, he accidentally aids Thao Lor, a young Hmong man who lives next door. The boy’s family, especially the girl’s sister, takes Walt under its wing, indenturing the boy to him to pay for trying to steal his Gran Torino. At first resistant—still feeling the scars from his in the Korean War—Walt eventually softens and becomes a friend and mentor to Thao, his sister, and their family. Beneath his rancorous and caustic exterior, Eastwood’s Kowalski is a wounded man unable to show his pain, but as he gets to know Thao—who is very much like some of the Koreans he killed—Walt can face his pain and find retribution. Notable for the supporting performances of Christopher Carley as Father Janovich and Dreama Walker as the smarmy Ashley.

Starring: Clint Eastwood, Bee Vang, Ahney Her, Brian Haley, John Carrol Lynch, Brian Howe, and Dreama Walker. Written by Nick Schenk and David Johansson. Directed by Clint Eastwood.

The Mule: Leo Sharp, (Eastwood), an amiable old florist who loses his business to internet competition, takes up an opportunity to become a drug runner for members of a Mexican drug cartel. Because of his age, race, clean record, and immaculate driving, Sharp is soon entrusted with huge shipments despite his reluctance to knuckle under to the cartel’s strict rules. When the cartel head is assassinated and replaced by a younger leader, Leo is coerced into continuing the cartel’s work after they learn the DEA is closing in on him. Interrupting a shipment to visit his gravely ill ex-wife, Leo finds himself surrounded. Unlike some other characters in Eastwood’s later works, Sharp is a likable, clever, charming, and good-hearted man that gets the most out of life whenever he can. He does find an opportunity to find forgiveness for past sins, and ultimately takes responsibility for his actions. Notable for Bradley Cooper’s supporting performance as a DEA agent.

Starring: Clint Eastwood, Bradley Cooper, Laurence Fishburne, Michael Pena, Dianne Wiest, Andy Garcia, and Alison Eastwood. Written by Nick Schenk. Directed by Clint Eastwood.

The Outlaw Josey Wales: After the end of the Civil War, Josey Wales (Eastwood), a member of Captain Anderson’s pro-confederate Missouri guerilla fighters, is asked to surrender. After the militia gives up their guns, they are brutally slaughtered by Union troops. Wales escapes, and, with a bounty on his head, Wales flees across the Western wilderness, accumulating some odd companions, including an old Cherokee, a young Navajo woman, and two survivors of a wagon train massacre, a woman and her granddaughter on their way to a relative’s farm. They eventually find the farm and settle in. After fending off an Indian attack, Wales is recognized by his old nemesis, Fletcher, who seeks to take him in. Eastwood’s performance here is much more representative of the younger Western hero that he played so often, but the humor and humanity of this revisionist Western is a foretaste of Eastwood’s future performances and works. Notable for Chief Dan George’s performance as Lone Watie.

Starring: Clint Eastwood, Chief Dan George, Sondra Locke, Bill McKinney, John Vernon, Sam Bottoms, and Sheb Wooley. Written by Phil Kaufman and Sonia Chamus. Directed by Clint Eastwood.

The Bridges of Madison County: In this departure from expectations, Eastwood plays Robert Kincaid, a National Geographic photographer who has traveled to Iowa to photograph some of its most noted covered bridges. There he meets Francesca Johnson (Meryl Streep) an Italian war bride. While her family is away, Francesca agrees to take Kincaid on a tour of local bridges during which they start a torrid four-day affair. She almost leaves with him but decides to stay—despite an unfulfilling marriage—to care for her children. After her death, her grown children recover a notebook recounting the affair. Eastwood was praised for his direction and cited for his ability to discover a moving love story at the heart of a somewhat vapid novel. Notable for Meryl Streep’s excellent performance as Francesca.

Starring: Clint Eastwood, Meryl Streep, Victor Slezak, Annie Corley, and Phyllis Lyons. Written by Richard LaGravenese from the novel by Robert James Waller. Directed by Clint Eastwood.

Pale Rider: A mysterious preacher (Eastwood) arrives at a California mining town besieged by Coy LaHood, (Richard Dysart) a ruthless mining baron. The preacher defends one of the miners, Hull Barret (Michael Moriarty), who is being beaten by LaHood’s men. They are chased off by the preacher who then fends off more attacks by LaHood in an attempt to steal the miners’ land. Things come to a head after one of the miners is assassinated in town. The Preacher and Hull attack LaHood’s camp with dynamite before heading into town for the final showdown. One of the most fascinating aspects of the film is the identity—or nature—of the Preacher. At times, he seems to have almost supernatural powers but is still inherently human. Notable for Moriarty’s fine performance.

Starring: Clint Eastwood, Carrie Snodgrass, Richard Dysart, Chris Penn, Sydney Penny, Richard Kiel, and John McGrath. Written by Michael Butler and Dennis Shryack. Directed by Clint Eastwood.

Bronco Billy: A comedy about a decrepit Wild West traveling circus helmed by hopeless romantic Bronco Billy (Eastwood). After his assistant quits, Antoinette Lily (Sondra Locke), a young woman swindled out of her fortune, agrees to join the show. Although the show is full of alcoholics, ex-cons, and other dregs of society, Miss Lily begins to warm to the crew but further misfortune causes the show to take extreme measures in order to stay alive. They end up entertaining the inmates of a mental institution where Miss Lily is forced to make a difficult choice. Critics liked Bronco Billy, citing it as an affable and funny intersection of the Old West and today’s world. Notable for the fine supporting cast, including Bill McKinney and Scatman Crothers.

Starring: Clint Eastwood, Sandra Locker, Scat Crothers, Geoffrey Lewis, Sam Bottoms, Bill McKinney, and Woodrow Parfrey. Written by Dennis Hackin. Directed by Clint Eastwood.

Thunderbolt and Lightfoot: Thunderbolt (Eastwood), a notorious bank robber, teams up with Lightfoot (Jeff Bridges), a goofy young man, who helps him escape from members of his old gang Red and Eddie (George Kennedy and Geoffrey Lewis) who mistakenly think he double-crossed them by taking the loot from a previous heist. Thunderbolt proposes robbing another bank using the same strategy. After the robbery, Red savagely beats Lightfoot before being apprehended by the law. Thunderbolt and Lightfoot manage to escape but make an interesting discovery on the way. Eastwood’s Thunderbolt contains elements of his typical hero type but also shows a humorous and paternal sensibility in his friendship with Lightfoot. Notable for Jeff Bridges’ great rendition of Lighfoot, a paragon of loose cannons.

Starring: Clint Eastwood, Jeff Bridges, George Kennedy, Geoffrey Lewis, Howard, Jack Dodson, and Garey Busey. Written and directed by Michael Cimino.

Play Misty for Me: One of Eastwood’s first directorial efforts, this psychological thriller tells the story of Dave Garver (Eastwood) a radio disc-jockey who is seduced and then stalked by Evelyn Draper (Jessica Walter) a fan whom he realizes is the caller who always requests “Misty” during his radio program. After she begins to display obsessive and violent behavior, Dave breaks up with her, but Evelyn won’t quit. Her obsession lands her in a mental hospital, but upon her release, she comes after Dave again, driving her obsession to a tragic conclusion. Eastwood’s taut, concise direction helped create one of the better suspense movies of its time. Notable for the final confrontation scene where Evelyn gets her comeuppance.

Starring: Clint Eastwood, Jessica Walter, Donna Mills, Donald Siegel, James McEaschin, and Jack Ging. Written by Jo Heims and Dean Riesner. Directed by Clint Eastwood.