Movies Like Playboy Playmates of the Year: The 90's

If you liked Playboy Playmates of the Year: The 90's (1999), 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
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
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.
3
X-Rated 2: The Greatest Adult Stars of All Time (2016)
★ 6.8/10
Documentary sequel that offers a close-up look into the personal lives of the legendary porn stars who've survived the test of time and influenced popular culture. Blends rare interviews with erotic clips and…
4
Aroused (2013)
★ 5.9/10
Get up close and personal with 16 of the most successful women in the adult film industry as they shed their clothes for an intimate photo shoot with director Deborah Anderson. As questions are asked, personal stories…
5
Cover Girl (1944)
★ 6.4/10
A nightclub dancer makes it big in modeling, leaving her dancer boyfriend behind.
6
Scandalous Sex (2004)
★ 6.9/10
A daughter seeks to restore the reputation of her disgraced father, a wronged college professor. With help of a professional student, she must overcome an ambitious sorority bitch and corrupt college dean.
7
Splendor (1999)
★ 6.2/10
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
8
Madonna: Truth or Dare (1991)
★ 6.2/10
From the rains of Japan, through threats of arrest for 'public indecency' in Canada, and a birthday tribute to her father in Detroit, this documentary follows Madonna on her 1990 'Blond Ambition' concert tour. Filmed…
9
Hot Girls Wanted (2015)
★ 6.1/10
A first-ever look at the realities of the professional “amateur” porn world and the steady stream of 18-to-19-year old girls entering into it.
10
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.
11
Step Up (2006)
★ 6.9/10
Delinquent Tyler Gage receives the opportunity of a lifetime after vandalizing a performing arts school, gaining him the chance to earn a scholarship and dance with up-and-coming dancer Nora.
12
Queen of the Ring (2025)
★ 6.8/10
In a time when pro wrestling for women was illegal all over the country, a small town single mother embraces the danger to change culture as she dominates America's most masculine sport to become the first million…
13
High Strung (2016)
★ 7/10
When a hip hop violinist busking in the New York subway encounters a classical dancer on scholarship at the Manhattan Conservatory of the Arts, sparks fly. With the help of a hip hop dance crew they must find a common…
14
The Notorious Bettie Page (2006)
★ 6.3/10
Bettie Page grew up in a conservative religious family in Tennessee and became a photo model sensation in 1950s New York. Bettie's legendary pin-up photos made her the target of a Senate investigation into pornography…
15
American Symphony (2023)
★ 6.5/10
Musician Jon Batiste attempts to compose a symphony as his wife, writer Suleika Jaouad, undergoes cancer treatment.
16
Life (2015)
★ 6/10
In 1955, young photographer Dennis Stock develops a close bond with actor James Dean while shooting pictures of the rising Hollywood star.
17
Gypsy (1962)
★ 6.4/10
Gypsy's mother Rose dreams of a life in show business for her daughters, but Louise becomes a huge burlesque star. Stage musical loosely based on the memoirs of Gypsy Rose Lee.
18
Nude (2017)
★ 9.2/10
NUDE explores perceptions of nudity in art by chronicling the creative process of photographer David Bellemere as he's commissioned by NU Muses founder Steve Shaw to shoot a fine art calendar of nude photographs.
19
Coyote Ugly (2000)
★ 6.3/10
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job…
20
Two Moon Junction (1988)
★ 6.1/10
A young Southern débutante temporarily abandons her posh lifestyle and upcoming, semi-arranged marriage to have a lustful and erotic fling with a rugged drifter who works at a local carnival.