Movies Like The Remarkable Mr. Pennypacker

If you liked The Remarkable Mr. Pennypacker (1959), a comedy movie directed by Henry Levin, 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
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…
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
Thunderstruck (2012)
★ 6.2/10Also comedy
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.
4
Love Happy (1949)
★ 5.8/10Also comedy
The Marx Brothers help young Broadway hopefuls when they get mixed up with gangsters due to a tin of sardines containing Romanoff diamonds.
5
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
6
Don't Tell Mom the Babysitter's Dead (1991)
★ 6.2/10Also comedy
Sue Ellen Crandell is a teenager eagerly awaiting her mother's summer-long absence. While the babysitter looks after her rambunctious younger siblings, Sue Ellen can party and have fun. But then the babysitter abruptly…
7
Godspell (1973)
★ 6.7/10Also comedy
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
8
The Ritz (1976)
★ 6/10Also comedy
To escape from a mobster, businessman Gaetano Proclo orders a cab driver to take him to a place where he can't be found. Unfortunately for Gaetano, the place turns out to be a gay bathhouse.
9
Trailer Park Boys: Don't Legalize It (2014)
★ 6.4/10Also comedy
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty…
10
Seriously Single (2020)
★ 6.8/10Also comedy
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
11
Coming 2 America (2021)
★ 6.3/10Also comedy
Prince Akeem Joffer is set to become King of Zamunda when he discovers he has a son he never knew about in America – a street savvy Queens native named Lavelle. Honoring his royal father's dying wish to groom this son…
12
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
13
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…
14
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
15
Animal Crackers (1930)
★ 6.9/10Also comedy
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…
16
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
17
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
18
The Importance of Being Earnest (1952)
★ 7.2/10Also comedy
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
19
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…
20
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.