Movies Like Keg o' My Heart

If you liked Keg o' My Heart (1933), a movie directed by Billy Gilbert, 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
Choke (2008)
★ 6.1/10
A sex-addicted con-man pays for his mother's hospital bills by playing on the sympathies of those who rescue him from choking to death.
2
Let's Make Love (1960)
★ 6.4/10
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
3
Born Yesterday (1950)
★ 7.3/10
Uncouth, loud-mouth junkyard tycoon Harry Brock descends upon Washington D.C. to buy himself a congressman or two, bringing with him his mistress, ex-showgirl Billie Dawn.
4
Send Me No Flowers (1964)
★ 6.8/10
When a hypochondriac assumes that he is dying, he makes an elaborate plan to ensure his wife's happiness. However, trouble ensues when she misunderstands his intentions.
5
Portal to Hell (2025)
★ 6/10
After a debt-collector finds a portal to hell in a washing machine at his local laundromat, he’s propositioned into feeding it sinners to save his neighbor’s soul, maybe even at the expense of his own.
6
The Dink (2026)
★ 6.4/10
Desperate to save a struggling country club and earn his father's respect, a washed-up tennis pro is compelled to break a sacred vow and do the unthinkable: play pickleball.
7
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
8
All or Nothing (2002)
★ 7.1/10
Penny works at a supermarket and Phil is a gentle taxi-driver. Penny’s love for Phil has run dry and they lead joyless lives with their two children, Rachel, a cleaner, and Rory, who is unemployed and aggressive.
9
The Happiest Millionaire (1967)
★ 6.8/10
A happy and unbelievably lucky young Irish immigrant, John Lawless, lands a job as the butler of an unconventional millionaire, Biddle. His daughter, Cordelia Drexel Biddle, tires of the unusual antics of her…
10
Oscar (1991)
★ 6.4/10
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…
11
The Other End of the Line (2007)
★ 6.5/10
An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
12
Carry On Doctor (1967)
★ 6.5/10
Francis Bigger, a notorious charlatan who tours the country lecturing on the subject of mind over matter, slips off the platform in the middle of his performance and ends up in hospital under the care of Dr Tinkle. The…
13
Where the Money Is (2000)
★ 5.9/10
Henry Manning has come up with a new way to break out of prison: fake a stroke and get transferred to a nursing home. It's a perfect plan, except for one thing: the woman assigned to take care of him at the nursing…
14
Jay Kelly (2025)
★ 6.1/10
Famous movie actor Jay Kelly embarks on a journey of self-discovery, confronting both his past and present, accompanied by his devoted manager, Ron.
15
Dinner in America (2022)
★ 7.8/10
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
16
The Distinguished Gentleman (1992)
★ 6/10
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
17
The 40 Year-Old Virgin (2005)
★ 6.4/10
Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers…
18
A Burlesque on Carmen (1915)
★ 5.8/10
A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.
19
Maverick (1994)
★ 6.9/10
Bret Maverick is a gambler who would rather con someone than fight them, and needs an additional $3k in order to enter a winner-takes-all poker game beginning in a few days. He joins forces with a woman with a…
20
The Onion Movie (2008)
★ 6.1/10
Venerable newscaster Norm Archer reports the latest news in politics, health, culture and entertainment - such as an automotive recall of decapitation-inducing "Neckbelts" and a study finding that "depression hits…