Movies Like How to Succeed with Girls

If you liked How to Succeed with Girls (1964), a comedy movie directed by Edward A. Biery, 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
The Cheyenne Social Club (1970)
★ 6.4/10Also comedy
Cowboy John O'Hanlan is surprised to learn that someone's left him a business in Cheyenne, Wyoming. He sets out to claim it, only to discover it's a brothel.
2
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends escape to a luxury spa retreat to reconnect, unwind and rediscover themselves, but their weekend of relaxation soon turns into a series of wild adventures and bad decisions.
3
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…
4
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
5
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.
6
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.
7
Whitney Cummings: Can I Touch It? (2019)
★ 6.7/10Also comedy
In her fourth stand-up special, Whitney Cummings returns to her hometown of Washington, D.C., and riffs on modern feminism, technology and more.
8
Iliza Shlesinger: War Paint (2013)
★ 6.5/10Also comedy
Her innocent appearance is just a cover for Last Comic Standing winner Iliza Shlesinger's acerbic, stream-of-conscious comedy that she unleashes on an unsuspecting audience in her hometown of Dallas in "War Paint," her…
9
Switching Channels (1988)
★ 6/10Also comedy
A television news chief courts his anchorwoman ex-wife with an eleventh-hour story.
10
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!
11
Iliza Shlesinger: Freezing Hot (2015)
★ 6.7/10Also comedy
Smart and brazen comedian Iliza Shlesinger shares her unflinchingly honest observations on the differences between men and women. Filled with hashtag-able catch phrases, this is a laugh-out-loud revelation exposing…
12
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
13
Batman and Harley Quinn (2017)
★ 6.2/10Also comedy
Batman and Nightwing are forced to team with the Joker's sometimes-girlfriend Harley Quinn to stop a global threat brought about by Poison Ivy and Jason Woodrue, the Floronic Man.
14
Held Up (1999)
★ 5.9/10Also comedy
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the…
15
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.
16
The Patsy (1964)
★ 6.2/10Also comedy
Eccentric bellhop Stanley Belt is recruited unexpectedly by the comedy team of a recently deceased entertainer. Stanley struggles to become a song-and-dance man as the team grooms him to become a star. But as the date…
17
The Paper Tigers (2020)
★ 6.7/10Also comedy
Three middle aged men polish their martial arts skills to avenge their fallen master.
18
Gotcha! (1985)
★ 6/10Also comedy
A student on a trip to France is tricked into smuggling secrets across the Iron Curtain by a sexy spy.
19
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
20
The Distinguished Gentleman (1992)
★ 6/10Also comedy
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…