
Will Penny
Will Penny, an aging cowpoke, takes a job on a ranch which requires him to ride the line of the property looking for trespassers or, worse, squatters. He finds that his cabin in the high mountains has been appropriated by a woman whose guide to Oregon has deserted her and her son. Too ashamed to kick mother and child out just as the bitter winter of the mountains sets in, he agrees to share the cabin until the spring thaw. But it isn't just the snow that slowly thaws; the lonely man and woman soon forget their mutual hostility and start developing a deep love for one another.
Movies Like Will Penny
Similar in style, tone, and themes — find your next watch.

The White Buffalo
1977★ 6.0
In this strange western version of Moby Dick, Wild Bill Hickok hunts a white buffalo he has seen in a dream. Hickok moves through a variety of uniquely authentic western locations - dim, filthy, makeshift taverns; freezing, slaughterhouse-like frontier towns and beautifully desolate high country - before improbably teaming up with a young Crazy Horse to pursue the creature.

Jeremiah Johnson
1972★ 7.3
A mountain man who wishes to live the life of a hermit becomes the unwilling object of a long vendetta by Indians when he proves to be the match of their warriors in one-on-one combat on the early frontier.

Oklahoma!
1955★ 6.6
In the Oklahoma territory at the turn of the twentieth century, two young cowboys vie with a violent ranch hand and a traveling peddler for the hearts of the women they love.

Open Range
2003★ 7.2
A former gunslinger is forced to take up arms again when he and his cattle crew are threatened by a corrupt lawman.

Chato's Land
1972★ 6.5
In 1870s New Mexico, a half-breed kills a bigoted sheriff in self-defense but the posse that eventually hunts him finds itself in dangerous territory.

Badland
2019★ 6.2
Detective Matthias Breecher, hired to track down the worst of the Confederate war criminals, roams the Old West seeking justice. His resolve is tested when he meets a determined pioneer woman who is far more than she seems.

The Shootist
1976★ 7.1
Afflicted with a terminal illness John Bernard Books, the last of the legendary gunfighters, quietly returns to Carson City for medical attention from his old friend Dr. Hostetler. Aware that his days are numbered, the troubled man seeks solace and peace in a boarding house run by a widow and her son. However, it is not Books' fate to die in peace, as he becomes embroiled in one last valiant battle.

The Jack Bull
1999★ 6.4
When the law fails to punish a fellow rancher that has abused his horses, a Wyoming horse trader sacrifices it all in a quest for justice.

Day of the Outlaw
1959★ 6.9
Blaise Starrett is a rancher at odds with homesteaders when outlaws hold up the small town. The outlaws are held in check only by their notorious leader, but he is diagnosed with a fatal wound and the town is a powder keg waiting to blow.

Warlock
1959★ 6.8
A band of murderous cowboys has imposed a reign of terror on the town of Warlock. With the sheriff humiliatingly run out of town, the residents hire the services of Clay Blaisedell as de facto town marshal. He arrives along with his friend, Tom Morgan, and sets about restoring law and order on his own terms whilst also overseeing the establishment of a gambling house and saloon.

Young Guns II
1990★ 6.5
Three of the original five "young guns" — Billy the Kid, Jose Chavez y Chavez, and Doc Scurlock — return in Young Guns, Part 2, which is the story of Billy the Kid and his race to safety in Old Mexico while being trailed by a group of government agents led by Pat Garrett.

Cowboy
1958★ 6.5
Chicago hotel clerk Frank Harris dreams of life as a cowboy, and he gets his chance when, jilted by the father of the woman he loves, he joins Tom Reece and his cattle-driving outfit. Soon, though, the tenderfoot finds out life on the range is neither what he expected nor what he's been looking for...

Last of the Dogmen
1995★ 6.8
A Montana bounty hunter is sent into the wilderness to track three escaped prisoners. Instead he sees something that puzzles him. Later with a female Native Indian history professor, he returns to find some answers.

Shoot Out
1971★ 6.4
Clay Lomax, a bank robber, gets out of jail after an 7 year sentence. He is looking after Sam Foley, the man who betrayed him. Knowing that, Foley hires three men to pay attention of Clay's steps. The things get complicated when Lomax, waiting to receive some money from his ex-lover, gets only the notice of her death and an 7 year old girl, sometimes very annoying, presumed to be his daughter.

Yellow Sky
1948★ 7.0
In 1867, a gang robs a bank and flees into the desert. Out of water, the outlaws encounter a ghost town called Yellow Sky and its only residents, a hostile young woman and her grandfather.

Monte Walsh
1970★ 6.3
Monte Walsh is an aging cowboy facing the ending days of the Wild West era. As barbed wire and railways steadily eliminate the need for the cowboy, Monte and his friends are left with fewer and fewer options. New work opportunities are available to them, but the freedom of the open prarie is what they long for. Eventually, they all must say goodbye to the lives they knew, and try to make a new start.

Colorado Territory
1949★ 7.0
After escaping from jail, outlaw Wes McQueen is convinced by his old partner in crime to do one last heist.

American Outlaws
2001★ 6.0
When a Midwest town learns that a corrupt railroad baron has captured the deeds to their homesteads without their knowledge, a group of young ranchers join forces to take back what is rightfully theirs. They will become the object of the biggest manhunt in the history of the Old West and, as their fame grows, so will the legend of their leader, a young outlaw by the name of Jesse James.

Wild Rovers
1971★ 6.1
Ross Bodine and Frank Post are cowhands on Walt Buckman's R-Bar-R ranch. Bodine is older and broods a bit about how he will get along when he's too old to cowboy. Post is young and rambunctious and ambitious for a better life than wrangling cows. When one of their fellow cowboys is killed in a corral accident, Post suggests a way into a better life for himself and his friend: robbing a bank. Bodine reluctantly joins in the plan and the two contrive to rob the local bank. They make good their escape initially, but Walt Buckman and his two sons, John and Paul, are incensed at this betrayal by their own trusted employees. John and Paul set out to bring Bodine and Post to justice.

The Last Wagon
1956★ 6.6
When a handful of settlers survive an Apache attack on their wagon train they must put their lives into the hands of Comanche Todd, a white man who has lived with the Comanches most of his life and is wanted for the murder of three men.