Clint Eastwood is one of the rare filmmakers who has made masterpieces in six different decades.
It almost goes without saying that Clint Eastwood is one of the greatest filmmakers of all time; he’s an icon for his acting work alone, as anyone who creates a character as beloved as “The Man With No Name” as Eastwood did in A Fisftful of Dollars, For A Few Dollars More, and The Good, The Bad, and The Ugly would be remembered forever. Sergio Leone’s trilogy isn’t even the only iconic western acting role of Eastwood’s career, so it comes as no faint praise to say that for as tremendous as he is as an actor, he’s an even greater director.
Part of Eastwood’s legacy has been his sheer level of commitment and hard work; he began directing with his criminally underrated 1971 thriller Play Misty For Me, and continues to add new projects to his schedule up until this day. Per Hollywood Reporter, Eastwood is currently working on the legal drama Juror #2, a legal drama that will star Nicholas Hoult, Toni Collete, and Zoey Deutch.
While Eastwood’s personal politics often drew criticisms from the more politically liberal Hollywood filmmakers, Roger Ebert defended his work by saying that “Clint Eastwood is one of the most admirable men in the history of motion pictures, and one of the few who has continued to grow in his art with every passing year.” He’s also one of the rare filmmakers who has made masterpieces in six different decades; here are the best films Eastwood made in each decade of his directorial career.
High Plains Drifter (1973)
High Plains Drifter is a quintessential Eastwood western that showed why his name is so synonymous with the genre. While Play Misty For Me showed that he could craft nail-biting thrillers set within the current day, High Plains Drifter proved that Eastwood had learned all the right lessons from his work with Leone.
He would return to the genre later on in the 1970s with the similarly excellent western The Outlaw Josey Wales; it’s a tough choice between two masterpieces of the genre, but the sheer darkness of High Plains Drifter made it stand out. Eastwood starred in the film as a remorseless, unnamed killer, and certainly pushed the film to the limits of its R-rating; it felt like a more brutal version of the same role he’s played in “The Man With No Name” trilogy.
Pale Rider (1985)
The 1980s saw Eastwood exploring a few different genres; he finally got the chance to direct one on the entries in the Dirty Harry series with Sudden Impact, and showed his interest in telling stories about the American military in 1986’s Heartbreak Ridge. Those that criticize Easwood’s conservatism are also likely unaware that he actually won a Golden Globe for directing Bird, a film that shed a spotlight on the underrated African-American musician Charlie “Bird” Parker, in what became a breakout role for Forest Whitaker.
However, that doesn’t mean that Eastwood had forgotten his roots;his 1985 film Pale Riderwas actually the highest-grossing western of the 1980s. It showed a maturation in Eastwood’s style, as his titular character represents a ghostly form of death that comes to defend the innocent civilians of a small town in California from a greedy group of oil prospectors.
Unforgiven (1992)
The 1990s saw Eastwood turning his interests towards crime thrillers with projects such as the electrifying thriller True Crime,
That being said, Unforgivenisn’t only Eastwood’s best western, but the film that finally won him the Academy Awards for Best Picture and Best Director that had long eluded him. It was the end of an era; Unforgiven felt like a “legacy sequel” to all of the iconic anti-heroes that Eastwood had played in the past.
Mystic River (2003)
Eastwood won his second Academy Awards for Best Picture and Best Director for 2004’s Million Dollar Baby, a film that also earned acting prizes for both Hilary Swank and Morgan Freeman; the fact that it wasn’t even the strongest work Eastwood did during the decade is another reason it’s impossible to underrate his filmography.
While Gran Torino and Invictus are also worthy candidates, Eastwood made one unforgettable film in 2003 that stands as his most emotional work to date. Mystic Riveris a riveting crime thriller that focuses on the collective trauma that childhood friends Jimmy Marcum (Sean Penn), Dave Boyle (Tim Robbins), and Detective Sean Devine (Kevin Bacon) received during childhood and continued to haunt them into adulthood.
American Sniper (2014)
Eastwood used the 2010s to explore many stories about real American heroes. While there were some critical disappointments such as The 15:17 to Paris and Hereafter, films like J. Edgar, Jersey Boys, Sully, and The Mule that some critics initially dismissed are deserving of reappraisal. However, American Sniper wasn’t just Eastwood’s most acclaimed film of the decade, but a box office sensation that made records for R-Rated films.
It’s certainly a divisive film due to Eastwood’s lionization of Chris Kyle (played brilliantly by Bradley Cooper), but it did feature some of the best combat sequences that he’s ever directed. It’s interesting that while Eastwood honors the men that served their country, he avoids making any direct statements about the Iraq War itself.
Cry Macho (2021)
While hopefully Juror #2 will be another great entry in Eastwood’s filmography, he already directed one satisfying salute to the western genre with 2021’s Cry Macho. In his final acting role, Eastwood plays a retired Texas rodeo star who takes on the last mission of his career when he helps transport the young boy Rafo (Eduardo Minett) back to his family in Mexico City, and becomes a paternal figure to him. It’s a very sweet, sensitive tribute to Eastwood’s association with the neo-Western genre, and proved that he was still capable of giving a movie star worthy performance.
Eastwood and Minetts’ chemistry elevates what could have been seen as melodrama, and the film has a surprisingly modern perspective on the notion of masculinity and what it truly means to be “macho.” Like Warner Brothers’ entire 2021 slate of releases, Cry Macho was simultaneously released both in theaters and on the HBO Max streaming service.