Movies Like Lucky Stiff

If you liked Lucky Stiff (2014), a comedy and music movie directed by Christopher Ashley, 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
A Song Is Born (1948)
★ 6.5/10Also comedy and music
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…
2
Love Happy (1949)
★ 5.8/10Also comedy and music
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
3
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
4
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
5
Footlight Parade (1933)
★ 6.8/10Also comedy and music
A fledgling producer finds himself at odds with his workers, financiers and his greedy ex-wife when he tries to produce live musicals for movie-going audiences.
6
The Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
7
Oscar (1991)
★ 6.4/10Also comedy
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
8
A Very Jonas Christmas Movie (2025)
★ 6.2/10Also comedy and music
Kevin, Nick, and Joe Jonas face a series of escalating obstacles as they struggle to make it from London to New York in time to spend Christmas with their families.
9
The Big Store (1941)
★ 6.3/10Also comedy and music
A detective is hired to protect the life of a singer, who has recently inherited a department store, from the store's crooked manager.
10
The Family Jewels (1965)
★ 6.5/10Also comedy
A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her.
11
A Mighty Wind (2003)
★ 6.8/10Also comedy and music
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.
12
Soul Men (2008)
★ 6.2/10Also comedy and music
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…
13
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
14
Tenacious D in The Pick of Destiny (2006)
★ 6.8/10Also comedy and music
In Venice Beach, naive Midwesterner JB bonds with local slacker KG and they form the rock band Tenacious D. Setting out to become the world's greatest band is no easy feat, so they set out to steal what could be the…
15
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
16
The Cocoanuts (1929)
★ 6.5/10Also comedy and music
During the Florida land boom, the Marx Brothers run a hotel, auction off some land and thwart a jewel robbery.
17
Moonwalkers (2015)
★ 6.1/10Also comedy
What if Apollo 11 never actually made it? What if, in reality, Stanley Kubrick secretly shot the famous images of the moon landing in a studio, working for the US administration? This is the premise of a totally…
18
The Honey Pot (1967)
★ 6.5/10Also comedy
In Venice, a millionaire hires an actor to help him prank three greedy exes into thinking he's dying and leaving his fortune to one of them.
19
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
20
Animal Crackers (1930)
★ 6.9/10Also comedy and music
The well-known explorer and hunter Captain Spaulding has just returned from Africa, and is being welcomed home with a lavish party at the estate of influential society matron Mrs. Rittenhouse when a valuable painting…