Movies Like Playboy Video Centerfold: Kimberley Conrad - Playmate of the Year 1989

If you liked Playboy Video Centerfold: Kimberley Conrad - Playmate of the Year 1989 (1989), a movie, 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
Lovelace (2013)
★ 6/10
Story of Linda Lovelace, who is used and abused by the porn industry at the behest of her coercive husband, before taking control of her life.
2
Bachelor Party (1984)
★ 6.3/10
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.
3
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
4
The Miracle of Morgan's Creek (1944)
★ 6.9/10
A small-town girl with a soft spot for American soldiers wakes up the morning after a wild farewell party for the troops to find that she married someone she can't remember.
5
The Wedding Ringer (2015)
★ 6.5/10
Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO…
6
Gail Daughtry and the Celebrity Sex Pass (2026)
★ 6.4/10
After her fiance sleeps with his celebrity crush, Kansas hairdresser Gail heads to Hollywood to even the score with her own famous fantasy — Jon Hamm.
7
What's New Pussycat? (1965)
★ 5.9/10
A playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own.
8
Born Yesterday (1950)
★ 7.3/10
Uncouth, loud-mouth junkyard tycoon Harry Brock descends upon Washington D.C. to buy himself a congressman or two, bringing with him his mistress, ex-showgirl Billie Dawn.
9
Skywalkers: A Love Story (2024)
★ 7.2/10
Two real-life daredevils test the limits of their love and trust by illegally scaling one of the world's tallest buildings to perform an acrobatic stunt.
10
Popstar: Never Stop Never Stopping (2016)
★ 6.6/10
When his new album fails to sell records, pop/rap superstar Conner4real goes into a major tailspin and watches his celebrity high life begin to collapse. He'll try anything to bounce back, anything except reuniting…
11
Ted (2012)
★ 6.5/10
John Bennett, a man whose childhood wish of bringing his teddy bear to life came true, now must decide between keeping the relationship with the bear or his girlfriend, Lori.
12
Orgazmo (1998)
★ 6.1/10
A devout Mormon living in L.A. becomes a pornographic actor after his martial arts moves impress a big-time director.
13
How to Murder Your Wife (1965)
★ 6.3/10
Stanley Ford is a successful cartoonist and happily single. That is, until he gets drunk at a friend's bachelor party and impulsively proposes to the beautiful woman who pops out of the cake. Once sober, he regrets the…
14
Celebrity (1998)
★ 6/10
The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of…
15
Magic Mike's Last Dance (2023)
★ 6.4/10
Mike Lane takes to the stage again after a lengthy hiatus, following a business deal that went bust, leaving him broke and taking bartender gigs in Florida. For what he hopes will be one last hurrah, Mike heads to…
16
Clash by Night (1952)
★ 6.7/10
An embittered woman seeks escape in marriage, only to fall for her husband’s best friend.
17
The Bronze (2016)
★ 6/10
In 2004, Hope Ann Greggory became an American hero after winning the bronze medal for the women's gymnastics team. Today, she's still living in her small hometown, washed-up and embittered. Stuck in the past, Hope must…
18
Swingers (1996)
★ 6.8/10
After 6 years together, Mike's girlfriend leaves him, so he travels to LA to be a star. Six months on, he's still not doing very well— so a few of his friends try to reconnect him to the social scene and hopefully help…
19
The Rainmaker (1956)
★ 6.8/10
Lizzie Curry is on the verge of becoming a hopeless old maid. Her wit and intelligence and skills as a homemaker can't make up for the fact that she's just plain plain! Even the town sheriff, File, for whom she harbors…
20
Down with Love (2003)
★ 6.1/10
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.