Movies Like $500 Reward

If you liked $500 Reward (1911), 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
The Adventure of Sherlock Holmes' Smarter Brother (1975)
★ 6/10Also comedy
After spending decades living in the shadow of his more famous and successful sibling, Consulting Detective Sigerson Holmes is called upon to help solve a crucial case that leads him on a hilarious trail of false…
2
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.
3
One Night at McCool's (2001)
★ 5.9/10Also comedy
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
4
How to Rob a Bank (2007)
★ 5.8/10Also comedy
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
5
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
6
Pups Alone (2021)
★ 5.8/10Also comedy
After receiving an exciting new job opportunity at a cutting edge Pet Invention company, Robert, his teenage daughter Jenna and their trusty and special border collie Charlie make the move to the new neighborhood…
7
Married to the Mob (1988)
★ 6/10Also comedy
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and…
8
Song of the Thin Man (1947)
★ 6.7/10Also comedy
While attending a glamorous jazz cruise on New York’s East River, Nick and Nora Charles witness the fatal shooting of a wealthy patron. When suspicion falls on a young bandleader and his musicians, the couple steps in…
9
The Cheap Detective (1978)
★ 6.4/10Also comedy
A spoof of the entire 1940s detective genre. San Francisco private detective, Lou Pekinpaugh is accused of murdering his partner at the instigation of his mistress—his partner's wife.
10
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
11
29th Street (1991)
★ 6.9/10Also comedy
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
12
Ca$h (2010)
★ 5.9/10Also comedy
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a…
13
Click & Collect (2018)
★ 6.6/10Also comedy
To save his daughter's Christmas, Andrew goes on a road trip with Dev, his neighbour from hell, to buy an elusive Sparklehoof the Unicorn Princess.
14
Wrong Cops (2013)
★ 6.1/10Also comedy
A group of bad cops look to dispose of a body that one of them accidentally shot.
15
Candy Cane Lane (2023)
★ 6/10Also comedy
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of…
16
A Bad Idea Gone Wrong (2017)
★ 6.4/10Also comedy
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
17
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
18
Family Plot (1976)
★ 6.8/10Also comedy
Spiritualist Blanche Tyler and her cab-driving boyfriend encounter a pair of serial kidnappers while trailing a missing heir in California.
19
Sherlock Jr. (1924)
★ 8/10Also comedy
A film projectionist longs to be a detective, and puts his meager skills to work when he is framed by a rival for stealing his girlfriend's father's pocketwatch.
20
Shadow of the Thin Man (1941)
★ 7/10Also comedy
While attending a major horse race with their young son, Nick Jr., Nick and Nora Charles witnesse a shocking murder from the crowded grandstand. What first appears to be an isolated killing soon leads to a maze of…