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Movies Like Riding Through Life with Love by My Side

If you liked Riding Through Life with Love by My Side (2018), a western and romance movie directed by Gary Winstead, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1Will Penny

    Will Penny (1967)

    ★ 6.7/10Also western and romance

    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…

  2. 2The Rainmaker

    The Rainmaker (1956)

    ★ 6.8/10Also romance and western

    Lizzie Curry is on the verge of becoming a hopeless old maid. Her wit and intelligence and skills as a homemaker can't make up for the fact that she's just plain plain! Even the town sheriff, File, for whom she harbors…

  3. 3Oklahoma!

    Oklahoma! (1955)

    ★ 6.6/10Also western and romance

    There's a box social coming up, and Curly asks Laurey if she'll be his date. Trouble is, Laurey thinks he's waited too long, and in a fit of pique accepts an offer from the boorish ranch hand Jud instead. Meanwhile…

  4. 4Ramrod

    Ramrod (1947)

    ★ 6.5/10Also western

    A cattle-vs.-sheepman feud loses Connie Dickason her fiance, but gains her his ranch, which she determines to run alone in opposition to Frank Ivey, "boss" of the valley, whom her father Ben wanted her to marry. She…

  5. 5Blood on the Moon

    Blood on the Moon (1948)

    ★ 6.2/10Also western and romance

    Down-and-out cowhand Jim Garry is asked by his old friend Tate Riling to help mediate a cattle dispute. When Garry arrives, however, it soon becomes clear that Riling has not been entirely forthright. Garry uncovers…

  6. 6The Fighting Kentuckian

    The Fighting Kentuckian (1949)

    ★ 6/10Also western and romance

    John Breen (John Wayne), a Kentucky militiaman falls in love with French exile Fleurette De Marchand (Vera Ralston). He discovers a plot to steal the land that Fleurette's exiles plan to settle on and aims to foil it.

  7. 7Dead for a Dollar

    Dead for a Dollar (2022)

    ★ 5.8/10Also western

    In 1897, veteran bounty hunter Max Borlund is deep into Mexico where he encounters professional gambler and outlaw Joe Cribbens — a sworn enemy he sent to prison years before. Max is on a mission to find and return…

  8. 8Two Rode Together

    Two Rode Together (1961)

    ★ 6.4/10Also western

    Two tough westerners bring home a group of settlers who have spent years as Comanche hostages.

  9. 9The Last Wagon

    The Last Wagon (1956)

    ★ 6.5/10Also western

    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…

  10. 10Barbarosa

    Barbarosa (1982)

    ★ 5.9/10Also western

    Karl Westover, an inexperienced farm boy, runs away after unintentionally killing a neighbor, whose family pursues him for vengeance. He meets Barbarosa, a gunman of near-mythical proportions, who is himself in danger…

  11. 11The Big Sky

    The Big Sky (1952)

    ★ 6.6/10Also western and romance

    Two tough Kentucky mountaineers join a trading expedition from St. Louis up the Missouri River to trade whisky for furs with the Blackfoot Indians. They soon discover that there is much more than the elements to…

  12. 12Crossfire Trail

    Crossfire Trail (2001)

    ★ 6.4/10Also romance and western

    Rafe Covington is as good as his word, and he's determined to keep his promise to a dying man that he'll look after the man's widow and Wyoming ranch. But the widow doubts the integrity of drifter Covington. And an…

  13. 13Angel and the Badman

    Angel and the Badman (1947)

    ★ 6.4/10Also western and romance

    A wounded outlaw finds unexpected mercy in the care of a rancher's daughter. The hope of love pulls him toward a different life until the law, and his violent past, close in on his new home. Now he must choose the kind…

  14. 14Man Without a Star

    Man Without a Star (1955)

    ★ 6.4/10Also western

    A wandering cowboy gets caught up in a range war.

  15. 15Sweetwater

    Sweetwater (2013)

    ★ 6.1/10Also western

    In the late 1800s, a fanatical religious leader, a renegade Sheriff, and a former prostitute collide in a blood triangle on the rugged plains of the New Mexico Territory.

  16. 16Monte Walsh

    Monte Walsh (2003)

    ★ 6.1/10Also western

    Monte Walsh and Chet Rollins are long-time cowhands, working whatever ranch work comes their way, but "nothing they can't do from a horse." Their lives are divided between months on the range and the occasional trip…

  17. 17Comanche Station

    Comanche Station (1960)

    ★ 6.7/10Also western

    A white man trades with the Comanche for the release of a female stranger and the pair cross paths with three outlaws who have their eyes on the handsome reward for bringing her home and Comanche on the warpath.

  18. 18The Tall Men

    The Tall Men (1955)

    ★ 6.4/10Also western and romance

    Two brothers discharged from the Confederate Army join a businessman for a cattle drive from Texas to Montana where they run into raiding Jayhawkers, angry Sioux, rough terrain and bad weather.

  19. 19Hondo

    Hondo (1953)

    ★ 6.5/10Also western

    Army despatch rider Hondo Lane discovers a woman and her son living in the midst of warring Apaches, and he becomes their protector.

  20. 20Love in Winterland

    Love in Winterland (2020)

    ★ 6.6/10Also romance

    Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.

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