Movies Like Playboy: Playmate Pajama Party

If you liked Playboy: Playmate Pajama Party (1999), a movie directed by Scott Allen, 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 Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
2
Star 80 (1983)
★ 6.5/10
Paul Snider is a narcissistic, small time hustler who fancies himself a ladies man. His life changes when he meets Dorothy Stratten working behind the counter of a Dairy Queen. Under his guidance Dorothy grows to fame…
3
Barbie: Big City, Big Dreams (2021)
★ 6.9/10
Barbie meets another Barbie Roberts, forming a close friendship, nicknaming each other Malibu and Brooklyn when they both attend the Handlers, Performing Art School in NYC, over the summer, competing for a spot at the…
4
The Benchwarmers (2006)
★ 5.9/10
A trio of guys try and make up for missed opportunities in childhood by forming a three-player baseball team to compete against standard little league squads.
5
The Many Adventures of Winnie the Pooh (1977)
★ 7.3/10
Whether we’re young or forever young at heart, the Hundred Acre Wood calls to that place in each of us that still believes in magic. Join pals Pooh, Piglet, Kanga, Roo, Owl, Rabbit, Tigger and Christopher Robin as they…
6
Pillow Talk (1959)
★ 7.1/10
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a…
7
My Awkward Sexual Adventure (2012)
★ 6.7/10
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
8
Don Jon (2013)
★ 6/10
A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.
9
High School Musical 2 (2007)
★ 6.5/10
The East High Wildcats are gearing up for big fun as they land the coolest summer jobs imaginable. Troy, Gabriella, Chad, and Taylor have scored sweet gigs at the Lava Springs Country Club owned by Sharpay and Ryan's…
10
Chasing Papi (2003)
★ 6.7/10
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored…
11
Ice Age: Collision Course (2016)
★ 6.1/10
Set after the events of Continental Drift, Scrat's epic pursuit of his elusive acorn catapults him outside of Earth, where he accidentally sets off a series of cosmic events that transform and threaten the planet. To…
12
Starship Troopers: Traitor of Mars (2017)
★ 5.9/10
Federation trooper Johnny Rico is ordered to work with a group of new recruits on a satellite station on Mars, where giant bugs have decided to target their next attack.
13
Tongues Untied (1990)
★ 6.7/10
Marlon Riggs, with assistance from other gay Black men, especially poet Essex Hemphill, celebrates Black men loving Black men as a revolutionary act. The film intercuts footage of Hemphill reciting his poetry, Riggs…
14
Brahms: The Boy II (2020)
★ 5.8/10
After a family moves into the Heelshire Mansion, their young son soon makes friends with a life-like doll called Brahms.
15
Magic Mike XXL (2015)
★ 6.1/10
Three years after Mike bowed out of the stripper life at the top of his game, he and the remaining Kings of Tampa hit the road to Myrtle Beach to put on one last blow-out performance.
16
A Good Old Fashioned Orgy (2011)
★ 5.8/10
A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.
17
Barbie and the Diamond Castle (2008)
★ 7.5/10
Liana and Alexa are best friends who share everything, including their love of singing. Upon meeting a girl inside a mirror, the duo embark on a journey that will put their friendship to the ultimate test.
18
Return of the Seven (1966)
★ 6.1/10
Chico, one of the remaining members of The Magnificent Seven, now lives in the town that they (The Seven) helped. One day someone comes and takes most of the men prisoner. His wife seeks out Chris, the leader of The…
19
Paint Your Wagon (1969)
★ 6.3/10
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…
20
Kiss Me, Stupid (1964)
★ 7/10
While traveling home from Vegas, an amorous lounge singer named Dino gets conned by a local mechanic/songwriter into staying in town for the night. The mechanic's songwriting partner, Orville, offers Dino his home for…