Five Essential... Films directed by Clint Eastwood

Gary Collinson selects his Five Essential Films directed by Clint Eastwood…

Despite a mantlepiece that boasts four Oscar statuettes (Best Director and Best Picture for both Unforgiven and Million Dollar Baby) and an Irving G. Thalberg Memorial Award, Hollywood legend Clint Eastwood remains synonymous with his on-screen persona while his talents as a filmmaker are often overlooked. Along with bringing classic characters such as ‘Dirty’ Harry Callahan and The Man With No Name to life, Clint has directed thirty movies (if one is to include his upcoming apartheid drama Invictus) in a career spanning almost forty years, and in addition to Academy recognition he is also the recipient of a host of respected honours. Obviously such an extensive catalogue is going to lead to differences in opinion, but here I present my picks for the five essential films directed by Clint Eastwood…

5. Gran Torino (2008)

Notable as his on-screen swansong (and perhaps the only film where his gun remains cold throughout), Clint stars as Korean War vet and retired automotive worker Walt Kowalski, a man confronted by his own mortality and lack of faith following the death of his wife. Despite his prejudice amid an influx of immigrants to the neighbourhood, Walt strikes up an unlikely friendship with the Asian family next door after catching teenager Thao trying to steal his treasured 1972 Ford Gran Torino as part of a gang initiation. Setting out to help the boy, Walt is soon forced to protect the family when the gangbangers seek retribution.




4. High Plains Drifter (1973)

Closely pipping The Outlaw Josey Wales (1976) as the first Western the list is High Plains Drifter - Clint’s second directorial effort and first take on the genre. Drawing inspiration from Sergio Leone’s celebrated Dollars Trilogy to mark a return to Man With No Name territory (albeit infused with elements of the supernatural), the film begins with the Stranger emerging from the desert on horseback and ends with him disappearing into the horizon. In between he is hired to protect the Arizona town of Lago from a corrupt mining company, although the townsfolk harbour a dark secret that links to the Stranger’s true motives.




3. Million Dollar Baby (2004)

Million Dollar Baby is a multi-award winning drama with Clint as boxing trainer Frankie Dunn, who sees a chance at redemption in female boxer Maggie Fitzgerald (Hilary Swank), along with one last shot at the big time. Under Frankie’s tutelage Maggie is soon heading for the top until a freak accident leaves a quadriplegic and the movie makes a dramatic narrative shift in focus. Inspired by F.X. Toole’s Rope Burns: Stories from the Corner and winner of four Academy Awards (Best Picture, Best Director, Best Actress – Hilary Swank and Best Supporting Actor – Morgan Freeman), Million Dollar Baby is both riveting and emotional and just misses out on second place by the narrowest of margins.



2. Mystic River (2003)

Based on Dennis Lehane’s novel, Mystic River is the only film on this list not to feature Eastwood in an on-screen role and relies instead on acting heavyweights Sean Penn and Tim Robbins, who were awarded Best Actor and Best Supporting Actor Oscars for their troubles. Penn stars as Jimmy, a Boston native whose daughter’s brutal murder brings back dark childhood memories for lifelong friend Dave (Robbins). A bleak masterpiece that deals with themes of child molestation and the impact of such crimes on victims’ lives, Mystic River is one of Clint’s most esteemed features and truly deserving of such high acclaim.




1. Unforgiven (1992)

First written in 1976 and purchased by Clint a few years later, Unforgiven is a classic Western that simultaneously honours and redefines the conventions of its genre. Clint headlines as reformed gunslinger and ex-drunkard Will Munny (a known thief and murderer, a man of notoriously vicious and intemperate disposition), who finds himself bringing up two children alone after the death of his wife. When a group of prostitutes offer a bounty on two cowboys responsible for carving one of them up, Will is approached by young upstart ‘The Schofield Kid’ to partner up on the hit. Joined by former running mate Ned (Morgan Freeman), the trio set off to the town of Big Whiskey to carry out the contract, much to the displeasure of local sheriff Little Bill (Gene Hackman, named Best Supporting Actor for his role), who fears an influx of gunfighters to his community. When the townsfolk murder Ned and display his body as a warning to others Munny doesn’t take too kindly to them decorating the saloon with his friend and soon returns to his merciless old ways. A fine climax to Eastwood’s career in the genre, Unforgiven is essential viewing and could easily be the greatest Western of all time.

Honourable Mentions

Play Misty for Me (1971)
The Outlaw Josey Wales (1976)
Bird (1986)
A Perfect World (1993)
Letters from Iwo Jima (2006)

Agree? Disagree? We'd love to hear your comments on the list...

Gary Collinson

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