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Movies like Trailing Trouble (1937)

The best movies like Trailing Trouble (1937) are Paint Your Wagon (1969), Go West (1940) and A Song Is Born (1948). If Trailing Trouble hooked you with its comedy and western, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Paint Your Wagon (1969)

    A Michigan farmer and a prospector form a partnership in the California gold country. Their adventures include buying and sharing a wife, hijacking a stage, kidnapping six prostitutes, and turning their mining camp into a boom town. Along the way there is plenty of drinking, gambling, and singing. They even find time to do some creative gold mining.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  2. Go West (1940)

    A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  3. A Song Is Born (1948)

    The story of seven scholars in search of an expert to teach them about swing music. They seem to have found the perfect candidate in winsome nightclub singer Honey Swanson. But Honey's gangster boyfriend doesn't want to give her up.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  4. A Mighty Wind (2003)

    Three eclectic, never-quite-famous folk bands come together for the first time in decades following the death of their manager to put on an reunion concert in his honor, at the request of his son.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  5. Blazing Saddles (1974)

    Crafty railroad worker Bart becomes the first Black sheriff of Rock Ridge, a frontier town about to be destroyed in order to make way for a new railroad. Initially, the citizens of Rock Ridge harbor a racial bias toward their new protector. However, they warm to him after realizing that Bart and his perpetually drunk gunfighter friend Jim are their only defense against a wave of thugs sent to rid the town of its population.

    Why it matches: Recommended by TMDB viewers · both western & comedy

    Worth the HypeMovies like this
  6. A Million Ways to Die in the West (2014)

    As a cowardly farmer begins to fall for the mysterious new woman in town, he must put his new-found courage to the test when her husband, a notorious gun-slinger, announces his arrival.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  7. Go West (1925)

    With little luck at keeping a job in the city a New Yorker tries work in the country and eventually finds his way leading a herd of cattle to the West Coast.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  8. Soul Men (2008)

    Two former backup soul singers, Louis and Floyd, have not spoken to each other in 20 years, and reluctantly agree to travel across the country together to a reunion concert to honor their recently-deceased lead singer. Cleo, a beautiful young woman who is believed to be Floyd's daughter, accompanies them as a new singer.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  9. Back to the Beach (1987)

    A former beach boy and his wife go to California to visit their daughter and become part of the new beach scene.

    Why it matches: Recommended by TMDB viewers · both comedy & music

  10. Bo Burnham: Make Happy (2016)

    Combining his trademark wit and self-deprecating humor with original music, Bo Burnham offers up his unique twist on life in this stand-up special about life, death, sexuality, hypocrisy, mental illness and Pringles cans.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Absolute CinemaMovies like this
  11. Way Out West (1937)

    Stan and Ollie try to deliver the deed to a valuable gold mine to the daughter of a dead prospector. Unfortunately, the daughter's evil guardian is determined to have the gold mine for himself and his saloon-singer wife.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Worth the HypeMovies like this
  12. The Apple Dumpling Gang (1975)

    A roving bachelor gets saddled with three children and a wealth of trouble when the youngsters stumble upon a huge gold nugget. They join forces with two bumbling outlaws to fend off the greedy townspeople and soon find themselves facing a surly gang of sharpshooters.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  13. Adam Sandler: 100% Fresh (2018)

    Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Worth the HypeMovies like this
  14. ¡Three Amigos! (1986)

    A trio of unemployed silent film actors are mistaken for real heroes by a small Mexican village in search of someone to stop a malevolent bandit.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this
  15. The After Party (2018)

    When an aspiring rapper goes viral for the wrong reasons, he thinks his career is sunk. But a wild party gives him one more chance to make it right.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  16. Rock 'n' Roll High School (1979)

    A group of rock-music-loving students, with the help of the Ramones, take over their school to combat its newly installed oppressive administration.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  17. Destry Rides Again (1939)

    Tom Destry, son of a legendary frontier peacekeeper, doesn’t believe in gunplay. Thus he becomes the object of widespread ridicule when he rides into the wide-open town of Bottleneck, the personal fiefdom of the crooked Kent.

    Why it matches: Recommended by TMDB viewers · both western & comedy

    Worth the HypeMovies like this
  18. Scooby-Doo! Shaggy's Showdown (2017)

    When the Scooby gang visits a dude ranch, they discover that it and the nearby town have been haunted by a ghostly cowboy, Dapper Jack, who fires real fire from his fire irons. The mystery only deepens when it’s discovered that the ghost is also the long lost relative of Shaggy Rogers!

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Worth the HypeMovies like this
  19. Airheads (1994)

    The Lone Rangers have heavy-metal dreams and a single demo tape they can't get anyone to play. The solution: Hijack an FM rock radio station and hold the deejays hostage until they agree to broadcast the band's tape.

    Why it matches: Recommended by TMDB viewers · both comedy & music

    Popcorn FlickMovies like this
  20. The Paleface (1948)

    Bob Hope stars in this laugh-packed wild west spoof co-starring Jane Russell as a sexy Calamity Jane, Hope is a meek frontier dentist, "Painless" Peter Potter, who finds himself gunslinging alongside the fearless Calamity as she fights off outlaws and Indians.

    Why it matches: Recommended by TMDB viewers · both comedy & western

    Popcorn FlickMovies like this

Like Trailing Trouble and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Trailing Trouble?

The closest matches to Trailing Trouble are Paint Your Wagon (1969), Go West (1940) and A Song Is Born (1948). Below are 17 more, each with the reason it matches.

What should I watch after Trailing Trouble?

Start with Paint Your Wagon (1969), the closest match to Trailing Trouble.

What is the highest-rated movie like Trailing Trouble?

Bo Burnham: Make Happy (2016), rated 8.0/10 by 459 TMDB users.

What is the newest movie like Trailing Trouble?

Adam Sandler: 100% Fresh (2018) is the most recent release on this list.

Are there English movies like Trailing Trouble?

Yes: Paint Your Wagon (1969), Go West (1940) and A Song Is Born (1948).

How are movies similar to Trailing Trouble chosen?

First come films that Trakt’s viewers watch alongside Trailing Trouble, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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