Movies Like Hold 'er Sheriff

If you liked Hold 'er Sheriff (1931), a comedy movie directed by Mack Sennett, 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
Destry Rides Again (1939)
★ 7.2/10Also comedy
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…
2
Go West (1940)
★ 6.6/10Also comedy
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.
3
The Bad Guys: Haunted Heist (2024)
★ 6.8/10Also comedy
The crafty Bad Guys crew embarks on a high-stakes Halloween heist to swipe a priceless amulet from a spooky mansion. What could go wrong?
4
Dog Gone (2008)
★ 6.5/10Also comedy
A courageous boy battles a gang of bumbling thieves to rescue a dog carrying a fortune in stolen diamonds.
5
Support Your Local Sheriff! (1969)
★ 6.9/10Also comedy
In the old west, a man becomes a Sheriff just for the pay, figuring he can decamp if things get tough.
6
Small Time Crooks (2000)
★ 6.5/10Also comedy
A loser of a crook and his wife strike it rich when a botched bank job's cover business becomes a spectacular success.
7
The League of Gentlemen (1960)
★ 7.1/10Also comedy
Involuntarily-retired Colonel Hyde recruits seven other dissatisfied ex-servicemen for a special project. Each of the men has a skeleton in the cupboard, is short of money, and is a service-trained expert in his field…
8
Two-Way Stretch (1960)
★ 6.7/10Also comedy
Three criminals plan to break out of prison the day before their release in order to carry out a daring jewel robbery, intending to establish the perfect alibi by returning to jail afterwards. First however they must…
9
Fun with Dick and Jane (2005)
★ 6.2/10Also comedy
After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty…
10
The Wrong Arm of the Law (1963)
★ 6.7/10Also comedy
The crooks in London know how it works. No one carries guns and no one resists the police. Then a new gang appears that go one better. They dress as police and steal from the crooks. This upsets the natural order of…
11
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
12
Playing with Fire (2019)
★ 6.6/10Also comedy
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
13
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
14
An American Tail: Fievel Goes West (1991)
★ 6.3/10Also comedy
Some time after the Mousekewitz's have settled in America, they find that they are still having problems with the threat of cats. That makes them eager to try another home out in the west, where they are promised that…
15
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
16
Scooby-Doo! Shaggy's Showdown (2017)
★ 7.7/10Also comedy
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…
17
Naked Gun 33⅓: The Final Insult (1994)
★ 6.5/10Also comedy
Frank Drebin is persuaded out of retirement to go undercover in a state prison. There he has to find out what top terrorist, Rocco, has planned for when he escapes. Adding to his problems, Frank's wife, Jane, is…
18
My Blue Heaven (1990)
★ 6.1/10Also comedy
FBI agent Barney Coopersmith is assigned to protect former Mafia figure turned informant Vincent Antonelli. In the witness protection program one is supposed to keep a low profile, but that is something that Antonelli…
19
Mr. Bones (2001)
★ 6/10Also comedy
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
20
The Sandlot 2 (2005)
★ 5.9/10Also comedy
A decade has passed in the small town where the original Sandlot gang banded together during the summer of ’62 to play baseball and battle the Beast. Now, back at the dugout, nine new kids descend on the diamond only…