Movies like $500 Reward (1911)
The best movies like $500 Reward (1911) are The Adventure of Sherlock Holmes' Smarter Brother (1975), Fun with Dick and Jane (1977) and One Night at McCool's (2001). If $500 Reward hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSherlock Jr. (1924)8.0/10 from 1,237 votes
- NewestAlfred Hitchcat Presents Banquo's Chair (2025)Released 2025
The Adventure of Sherlock Holmes' Smarter Brother (1975)
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 identities, stolen documents, secret codes... and exposed backsides.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisOne Night at McCool's (2001)
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 tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisHow to Rob a Bank (2007)
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMerry Christmas, Drake & Josh (2008)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBottle Rocket (1993)
Dysfunctional friends Dignan and Anthony plan and execute a robbery with their pot-growing friend, Bob. The short film that inspired Wes Anderson’s feature debut.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Cheap Detective (1978)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMarried to the Mob (1988)
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 her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisWrong Cops (2013)
A group of bad cops look to dispose of a body that one of them accidentally shot.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Pink Panther Strikes Again (1976)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCa$h (2010)
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 tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisFamily Plot (1976)
Spiritualist Blanche Tyler and her cab-driving boyfriend encounter a pair of serial kidnappers while trailing a missing heir in California.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShadow of the Thin Man (1941)
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 corruption, blackmail, gambling scandals, and criminal intrigue. As Nick investigates, he encounters suspicious bookmakers, dishonest officials, rival gangsters, and a mysterious killer determined to stay ahead of the law. Nora, as always, is never far from the action, bringing her quick wit and fearless curiosity to the case.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHard to Die (1990)
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 of killings six months previously, is at the bottom of the whole thing. Little do they know the real horror that they face in the end.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCandy Cane Lane (2023)
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 Christmas to life, unleashing chaos on the small unsuspecting town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSherlock Jr. (1924)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisTwo-Way Stretch (1960)
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 get out, a task made more difficult by a new, stricter prison officer.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPups Alone (2021)
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, right before Christmas. Upon arriving, Robert meets his gorgeous next door neighbor Holly, and her sassy and spunky border collie Gidget. Before the sparks can fly, they are set upon my Robert’s conniving and obnoxious next door neighbor and project manager Victor, his neighborhood bully bulldog “Vinnie P” and the sycophantic sidekick Chihuahua “Jose”.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMiss Sherlock Holmes (1908)
Nell, the boss's daughter, uses Sherlock Holmes' detective work, to choose between the two suitors at her dad's broker's office.
Why it matches: Similar story and style · both comedy
Sherlock Bonehead (1914)
Chief of Police Ivorytop and Chief of Detectives Sherlock Bonehead, of Rottenport, fall in love with Helen, a girl from the city
Why it matches: Similar story and style · both comedy
A Villainous Villain (1916)
The master crook steals the sweetheart of Sherlock, a great detective. Sherlock undertakes to recover her.
Why it matches: Similar story and style · both comedy
Alfred Hitchcat Presents Banquo's Chair (2025)
Another Purradise Ranch production with “talking cat actors,” featuring Detective Purrlock Holmes investigating a murder in a mansion haunted by feline ghosts.
Why it matches: Similar story and style · both comedy
The Private Life of Sherlock Holmes (1970)
When a bored Sherlock eagerly takes the case of Gabrielle Valladon following an attempt on her life, the search for her missing husband leads to Loch Ness and the legendary monster.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Seven-Per-Cent Solution (1976)
Concerned about his friend's cocaine use, Dr. Watson tricks Sherlock Holmes into travelling to Vienna, where Holmes enters the care of Sigmund Freud. Freud attempts to solve the mysteries of Holmes' subconscious, while Holmes devotes himself to solving a mystery involving the kidnapping of Lola Deveraux.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThey Might Be Giants (1971)
After the death of his wife, retired judge Justin Playfair creates a fantasy world for himself in which he is the legendary detective Sherlock Holmes, even dressing like the character. Out of concern for Justin's money more than his health, his brother Blevins puts him under the care of psychiatrist Dr. Mildred Watson. As Dr. Watson grows fond of Justin, she begins to play along with his theories, eventually becoming an assistant in his investigations.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Hound of the Baskervilles (1988)
When a nobleman is threatened by a family curse on his newly inherited estate, detective Sherlock Holmes is hired to investigate.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisTom and Jerry Meet Sherlock Holmes (2010)
Tom and Jerry need to learn to work together in order to help Sherlock Holmes with an investigation of a jewel theft. But still, they are cat and mouse!
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSherlock Holmes et l'Aventure du Diamant Bleu (2023)
Sherlock and Doctor Watson are back and investigate the curious disappearance of an exceptional diamond in a hotel room. A theater adaptation of one of the 56 short stories featuring the detective Sherlock Holmes.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like $500 Reward?
The closest matches to $500 Reward are The Adventure of Sherlock Holmes' Smarter Brother (1975), Fun with Dick and Jane (1977) and One Night at McCool's (2001). Below are 27 more, each with the reason it matches.
What should I watch after $500 Reward?
Start with The Adventure of Sherlock Holmes' Smarter Brother (1975), the closest match to $500 Reward.
What is the highest-rated movie like $500 Reward?
Sherlock Jr. (1924), rated 8.0/10 by 1,237 TMDB users.
What is the newest movie like $500 Reward?
Alfred Hitchcat Presents Banquo's Chair (2025) is the most recent release on this list.
Are there English movies like $500 Reward?
Yes: The Adventure of Sherlock Holmes' Smarter Brother (1975), Fun with Dick and Jane (1977) and One Night at McCool's (2001).
How are movies similar to $500 Reward chosen?
First come films that Trakt’s viewers watch alongside $500 Reward, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.