Clint Eastwood’s movies are a joy to watch, though not always for the whole family. From his early days starring in the Man With No Name trilogy to his later movies like The Pale Rider, Eastwood’s roles, typically as the ‘strong, silent type’ are a great reminder of the essence of what America means to many of us.
Why not dive back into Eastwood’s career arc? Here are Bigtime FYI’s 9 Clint Eastwood movie recommendations to cozy up to next to the fireplace and a hot chocolate (or hot toddy).
The Man With No Name Trilogy (1964-1966)
Directed by Italian film maker Sergio Leone, The Dollars Trilogy (aka The Man With No Name Trilogy) put Eastwood on the map as an up-and-coming actor in Hollywood. In the trilogy, Eastwood plays a series of quiet, strategic drifters with loose morals and a “go screw yourself” attitude; the plots revolve around various schemes hatched by Eastwood’s character, often playing enigmatic bad guys against eachother for his own gain.
Throughout the trilogy, Eastwood is supported by an amazing group of actors, not least of which was Lee Van Cleef.
High Plains Drifter (1973)
Clint Eastwood directs and starred in High Plains Drifter, a grueling and at times shocking western that hit theaters in 1973. The plot of Drifter is extremely dark—Eastwood’s character shows up to a town, rapes a woman, takes control of the town, gets drunk throughout the course of the film, and leads the townspeople into an apocalyptic climax scene. High Plains Drifter is in fact close to a horror movie, as close to a horror movie as an American western ever got.
Word of advice: Do NOT watch with the kids or grandkids.
Pale Rider (1985)
Pale Rider, another Eastwood-directed and starred film, is thought by many to be a sequel—or at least related—to High Plains Drifter. Eastwood’s character, again a strong, silent type, unafraid to stare down danger, is much tamer and morally straight than his precursor in High Plains Drifter.
Still, the movie is classic Eastwood, classic American western. This one’s probably OK to watch with the grandkids.
The Outlaw Josey Wales (1976)
Set during and after the American Civil War, The Outlaw Josey Wales follows Josey Wales, played by Clint Eastwood, as he goes on a quest for revenge after a group of Union soldiers murder his family. Quiet and brooding, Josey Wales doesn’t talk much, but communicates all he needs to with his guns.
Every Which Way But Loose (1978) & Any Which Way You Can (1980)
This hilarious series of action comedies, front-run by Eastwood, are classic late-70s film canon, and full of good old nostalgia. In them, Eastwood shows off his boxing skills—some of the most epic moments in these two movies are the great fist fight sequences.
His trusty sidekick is bizarre, but maybe not so much for a film coming out of the late 70s: an orangutan named Clyde. Eastwood and Clyde the orangutan take on a group of biker outlaws called “The Black Widows” in his trusty red pickup truck, hilarious hijinx ensuing throughout.
Kelly’s Heroes (1970)
Our last recommendation here, Kelly’s Heroes is an amazing American war film with one of the best casts of any movie released in the 70s. Starring Eastwood, Don Rickles, Harry Dean Stanton, and Donald Sutherland, among other great supporting actors, if you haven’t seen this one yet, put it up next in your queue.
Set in WWII, Kelly’s Heroes follow a group of American soldiers gone AWOL to rob a bank behind enemy lines. Suffice to say, while this movie is set in a war, it feels exactly like a western—and we all know how good Eastwood plays those.
