Movies Like Deep Inside Jill Kelly

If you liked Deep Inside Jill Kelly (2001), 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
Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972)
★ 6.5/10
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and…
2
Fifty Shades of Grey (2015)
★ 5.9/10
When college senior Anastasia Steele steps in for her sick roommate to interview prominent businessman Christian Grey for their campus paper, little does she realize the path her life will take. Christian, as enigmatic…
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
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
5
Eyes Wide Shut (1999)
★ 7.5/10
After Dr. Bill Harford's wife, Alice, admits to having sexual fantasies about a man she met, Bill becomes obsessed with having a sexual encounter. He discovers an underground sexual group and attends one of their…
6
Young People Fucking (2007)
★ 5.9/10
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…
7
Aileen: Queen of the Serial Killers (2025)
★ 7/10
Aileen Wuornos remains a rarity: a female serial killer. From childhood abuse to death-row revelations, this documentary revisits her life and crimes.
8
Fairy Tales (1978)
★ 6/10
On his twenty-first birthday, the Prince goes on a quest that takes him across the land searching for the one woman that gets him sexually excited, Princess Sleeping Beauty.
9
The Mating Habits of the Earthbound Human (1999)
★ 6/10
David Hyde Pierce, playing an alien (credited as infinity-cubed in the opening credits), narrates a courtship in a late-20th century American city as an extraterrestrial nature documentary. The relationship "footage"…
10
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.
11
Fear the Night (2023)
★ 5.9/10
During a bachelorette party in a secluded California farmhouse, masked intruders launch a brutal attack, forcing eight women to fight for survival. Led by Tess, a troubled military veteran, they unite to defend…
12
Orgasm Inc: The Story of OneTaste (2022)
★ 6.1/10
A sexual wellness company gains fame and followers, then members come forward with shocking allegations.
13
Shortbus (2006)
★ 6.2/10
In post-9/11 New York City, an eclectic group of citizens find their lives entangled, personally, romantically, and sexually, at Shortbus, an underground Brooklyn salon infamous for its blend of art, music, politics…
14
Pink Flamingos (1972)
★ 6.1/10
Notorious Baltimore criminal and underground figure Divine goes up against Connie & Raymond Marble, a sleazy married couple who make a passionate attempt to humiliate her and seize her tabloid-given title as "The…
15
Pamela, a love story (2023)
★ 7/10
In her own words, through personal video and diaries, Pamela Anderson shares the story of her rise to fame, rocky romances and infamous sex tape scandal.
16
Polyester (1981)
★ 7/10
Blessed with a keen sense of smell and cursed with a philandering pornographer husband, a parasitic mother, and a pair of delinquent children, the long-suffering Francine Fishpaw turns to the bottle as her life falls…
17
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…
18
X (2011)
★ 6.4/10
A veteran call girl and a runaway prostitute witness a murder which sends them on an out-of-control roller coaster ride through the twilight zone of sex-for-sale.
19
McQueen (2018)
★ 7.4/10
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own…
20
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…