Movies like Playboy: Playmate Pajama Party (1999)
The best movies like Playboy: Playmate Pajama Party (1999) are The Bachelor and the Bobby-Soxer (1947), Star 80 (1983) and Barbie: Big City, Big Dreams (2021). If Playboy: Playmate Pajama Party hooked you, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedBarbie and the Diamond Castle (2008)7.5/10 from 903 votes
- NewestBruce Willis : les secrets d'une icône (2025)Released 2025
The Bachelor and the Bobby-Soxer (1947)
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 date Susan until the crush abates.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisStar 80 (1983)
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 as a Playboy Playmate. But when Dorothy begins pursuing an acting career, the jealous Paul finds himself elbowed out of the picture by more famous men.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisBarbie: Big City, Big Dreams (2021)
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 spotlight solo.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Benchwarmers (2006)
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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThe Many Adventures of Winnie the Pooh (1977)
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 enjoy their days together and sing their way through adventures.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMy Awkward Sexual Adventure (2012)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDon Jon (2013)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPillow Talk (1959)
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 complaint against him, Brad sets about to seduce her in the guise of a sincere and upstanding Texas rancher. When mutual friend Jonathan discovers that his best friend is moving in on the girl he desires, however, sparks fly.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisChasing Papi (2003)
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 socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHigh School Musical 2 (2007)
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 family. Sharpay's first rule of business: Get Troy. As Troy experiences a life of privilege he's never known, will he give up the Wildcats and Gabriella to rise to the top?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIce Age: Collision Course (2016)
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 save themselves from peril, Manny, Sid, Diego, and the rest of the herd leave their home and embark on a quest full of thrills and spills, highs and lows, laughter and adventure while traveling to exotic new lands and locations.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisStarship Troopers: Traitor of Mars (2017)
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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisPaint Your Wagon (1969)
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 into a boom town. Along the way there is plenty of drinking, gambling, and singing. They even find time to do some creative gold mining.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLife (2015)
In 1955, young photographer Dennis Stock develops a close bond with actor James Dean while shooting pictures of the rising Hollywood star.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisBrahms: The Boy II (2020)
After a family moves into the Heelshire Mansion, their young son soon makes friends with a life-like doll called Brahms.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisA Good Old Fashioned Orgy (2011)
A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisMagic Mike XXL (2015)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisBrats (1930)
Stanley and Oliver are trying to spend a relaxing night at home playing checkers, but the antics of their mischievous sons keep interrupting their recreation.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisReturn of the Seven (1966)
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 Seven for help. Chris also meets Vin another member of The Seven. They find four other men and they go to help Chico.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisBarbie and the Diamond Castle (2008)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMr. Love (1986)
An fifty-year-old mild-mannered gardener becomes a lovable legend in his town for his talent to romantically please every woman that fancies him.
Why it matches: Similar story and style
Trophy Kids (2011)
To win the celebrity and self-made wealth he craves, an aimless, twenty-something Manhattan playboy devises a film based on his party-boy, club-going lifestyle, and hires a self-destructive aspiring playwright to ghost the feature script. As the mismatched pair struggles to complete the script and get a handle on their misdirected lives, they reveal the sometimes comedic, sometimes tragic behaviors of 'Generation Y'- a generation taught to believe each was incomparably special and messianically gifted. Though they begin to vie for the affections of the same girl, and their chance at success and happiness threatens to crumble, they ultimately each find their own, unique life truths.
Why it matches: Similar story and style
Marilyn Monroe: The Last Torments (2011)
Nearly fifty years after her death, Marilyn Monroe remains an absolute icon, the image of a superficial and sensual blonde forever etched in the collective imagination. But behind the legend lies a more complex reality: that of Norma Jeane Baker, a young woman abandoned by all who constantly lurched from euphoria to the depths of despair. Throughout her life, Marilyn attempted to free herself from her image and access her truth. You will discover the little-known episodes from the last years of the star's life. Why did she abandon Hollywood and move to New York under an assumed name in 1954? How did she end up locked away in a psychiatric clinic after filming "The Misfits"? What did her diaries contain? What was her relationship with her psychoanalyst? Finally, under what circumstances did this 36-year-old woman meet her death? Using numerous testimonies and archival material, the teams paint a portrait of a mysterious and tormented personality.
Why it matches: Similar story and style
The Opposite Sex (2015)
The story of Vince, New England's most successful divorce attorney. To Vince, life is one big competition, and losing is unacceptable. This also applies in his dating life with his love 'em and leave 'em approach. Then Vince meets Jane, who is beautiful, successful and also extremely driven. Together they enter into a series of entertaining wagers with each other where the winner gets to decide the fate of the loser.
Why it matches: Similar story and style
SnoozefestMovies like thisThat's Her (TBA)
The story follows a corporate-climbing playboy who falls for a girl-next-door office temp and a high-powered executive. He must choose between love and advancing his career.
Why it matches: Similar story and style
My Best Friend's Girl (2008)
Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
Why it matches: Similar story and style
SnoozefestMovies like thisWhat a Widow! (1930)
A young woman's elderly husband dies and leaves her $5 million. She travels to Paris and becomes part of the "Continental" set and is pursued by a rich playboy and a lawyer who works for her.
Why it matches: Similar story and style
Bruce Willis : les secrets d'une icône (2025)
Nothing predestined Bruce Willis to become an actor, still less of action movies, and yet in a few years he would become one of the most profitable stars in the entire history of cinema, until his career abruptly changed course. For ten years, Bruce Willis had been going through a dry spell, punctuated by dozens of low-budget films.
Why it matches: Similar story and style
Anna Nicole Smith: Exposed (1998)
A fictionalized day in the life of Anna Nicole Smith, revealing her innermost thoughts on the people (friends, servants, lawyers, photographers) and events (photoshoots, bathing, sexual exploits) that make up her life.
Why it matches: Similar story and style
Alfie (1966)
A young man leads a promiscuous lifestyle until several life reversals make him rethink his purposes and goals in life.
Why it matches: Similar story and style
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Playboy: Playmate Pajama Party?
The closest matches to Playboy: Playmate Pajama Party are The Bachelor and the Bobby-Soxer (1947), Star 80 (1983) and Barbie: Big City, Big Dreams (2021). Below are 27 more, each with the reason it matches.
What should I watch after Playboy: Playmate Pajama Party?
Start with The Bachelor and the Bobby-Soxer (1947), the closest match to Playboy: Playmate Pajama Party.
What is the highest-rated movie like Playboy: Playmate Pajama Party?
Barbie and the Diamond Castle (2008), rated 7.5/10 by 903 TMDB users.
What is the newest movie like Playboy: Playmate Pajama Party?
Bruce Willis : les secrets d'une icône (2025) is the most recent release on this list.
Are there English movies like Playboy: Playmate Pajama Party?
Yes: The Bachelor and the Bobby-Soxer (1947), Star 80 (1983) and Barbie: Big City, Big Dreams (2021).
How are movies similar to Playboy: Playmate Pajama Party chosen?
First come films that Trakt’s viewers watch alongside Playboy: Playmate Pajama Party, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.