Movies Like Where the Devil Can't Go, He Sends a Woman

If you liked Where the Devil Can't Go, He Sends a Woman (2022), a comedy and history movie directed by Heathcliff Janusz Iwanowski, 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
Goltzius & the Pelican Company (2012)
★ 6.1/10Also comedy and history
Hendrik Goltzius, a late-16th-century Dutch printer and engraver of erotic prints, seduces the Margrave of Alsace into paying for a printing press to make and publish illustrated books.
2
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.
3
Start the Revolution Without Me (1970)
★ 6.1/10Also comedy and history
Two sets of identical twins are accidentally switched at birth. One pair, Phillipe and Pierre DeSisi, are aristocratic and haughty, while the other, Charles and Claude Coupé, are poor and dim-witted. On the eve of the…
4
Dave Chappelle: The Unstoppable... (2025)
★ 6.7/10Also comedy
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
5
The F**k-It List (2020)
★ 6/10Also comedy
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
6
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
7
Surfers’ Time (2005)
★ 6.3/10Also comedy
Three young guys got work from unlucky gangster... they try to make a great job but everything goes wrong
8
Eddie Murphy Raw (1987)
★ 7.2/10Also comedy
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
9
Bottle Rocket (1993)
★ 6.2/10Also comedy
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.
10
A Night at the Opera (1935)
★ 7.4/10Also comedy
The Marx Brothers take on high society and the opera world to bring two lovers together. A sly business manager and two wacky friends of two opera singers help them achieve success while humiliating their stuffy and…
11
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
12
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
13
What Did You Do in the War, Daddy? (1966)
★ 5.9/10Also comedy
A by-the-book Captain is ordered to capture a strategic village in Italy. The Italian soldiers are willing to surrender, if they can have a festival first. The lieutenant convinces the Captain this is the only way…
14
Dylan Moran: Like, Totally (2006)
★ 7.7/10Also comedy
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
15
68 Kill (2017)
★ 5.9/10Also comedy
Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.
16
The Draughtsman's Contract (1982)
★ 7.1/10Also history and comedy
R. Neville, a brash young draftsman, is hired to make a dozen landscape illustrations at the estate of Mr Herbert and his wife Virginia. Aside from monetary compensation, the arrangement includes a sexual liaison…
17
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
18
Adam Sandler: 100% Fresh (2018)
★ 7.1/10Also comedy
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
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
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.