Movies Like Times Square Playboy

If you liked Times Square Playboy (1936), a comedy movie directed by William C. McGann, 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 Hangover Part III (2013)
★ 6.2/10Also comedy
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
2
Way Out West (1937)
★ 7.1/10Also comedy
Stan and Ollie try to deliver the deed to a valuable gold mine to the daughter of a dead prospector. Unfortunately, the daughter's evil guardian is determined to have the gold mine for himself and his saloon-singer wife.
3
Paint Your Wagon (1969)
★ 6.3/10Also comedy
A Michigan farmer and a prospector form a partnership in the California gold country. Their adventures include buying and sharing a wife, hijacking a stage, kidnapping six prostitutes, and turning their mining camp…
4
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
5
Go West (1940)
★ 6.6/10Also comedy
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
6
The Apple Dumpling Gang (1975)
★ 6.6/10Also comedy
A roving bachelor gets saddled with three children and a wealth of trouble when the youngsters stumble upon a huge gold nugget. They join forces with two bumbling outlaws to fend off the greedy townspeople and soon…
7
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.
8
The Railrodder (1965)
★ 6.8/10Also comedy
After literally swimming across the Atlantic Ocean, an Englishman takes a country trip across Canada on a railcar.
9
Woody Woodpecker (2017)
★ 6.6/10Also comedy
Woody Woodpecker enters a turf war with a big city lawyer wanting to tear down his home in an effort to build a house to flip.
10
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10Also comedy
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
11
LEGO Scooby-Doo! Haunted Hollywood (2016)
★ 7.2/10Also comedy
The gang find themselves in a tinsel-town twist! While on a VIP tour of the legendary Brickton Studios, Scooby and friends get a first-hand experience of the rumored hauntings when classic movie monsters drop in for a…
12
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.
13
Sherlock Jr. (1924)
★ 8/10Also comedy
A film projectionist longs to be a detective, and puts his meager skills to work when he is framed by a rival for stealing his girlfriend's father's pocketwatch.
14
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…
15
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.
16
The Bad Guys: Haunted Heist (2024)
★ 6.8/10Also comedy
The crafty Bad Guys crew embarks on a high-stakes Halloween heist to swipe a priceless amulet from a spooky mansion. What could go wrong?
17
Johnny English Strikes Again (2018)
★ 6.3/10Also comedy
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep…
18
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.
19
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
20
You're Never Too Young (1955)
★ 6.6/10Also comedy
When an aspiring barber becomes inadvertently involved in the theft of a valuable diamond, necessity forces him to masquerade as a 12 year-old child - with humorous consequences.