Movies Like Deep Inside Jill Kelly

If you liked Deep Inside Jill Kelly (2002), a movie directed by Veronica Hart, 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
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.
3
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…
4
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…
5
Horrible Bosses 2 (2014)
★ 6.2/10
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
6
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…
7
sex, lies, and videotape (1989)
★ 7/10
Ann, a frustrated wife, enters into counseling due to a troubled marriage. Unbeknownst to her, her husband John has begun an affair with her sister. When John’s best friend Graham arrives, his penchant for interviewing…
8
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.
9
Zerophilia (2005)
★ 5.9/10
Luke, a young man insecure about his masculinity, discovers he's a Zerophiliac, with the ability to change sex at will. Join Luke as he journeys into the extraordinary world of Zerophilia where so many crazy questions…
10
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…
11
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.
12
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.
13
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.
14
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
15
Beavis and Butt-Head Do the Universe (2022)
★ 6.9/10
In 1998, Beavis and Butt-Head are sentenced to Space Camp by a “creative” judge. Their obsession with a docking simulator (huh huh) leads to a trip on the Space Shuttle, with predictably disastrous results. After going…
16
Crimes of Passion (1984)
★ 6.3/10
Fashion designer Joanna Crane leads a double life. By night she is China Blue, a prostitute who's attracted the attention of a sexually frustrated private detective, and a psychopathic priest in possession of a…
17
Love & Other Drugs (2010)
★ 7/10
Maggie is an alluring free spirit who won't let anyone – or anything – tie her down. But she meets her match in Jamie, whose relentless and nearly infallible charm serves him well with the ladies and the cutthroat…
18
Going the Distance (2010)
★ 6.1/10
Erin and Garrett are very much in love. When Erin moves to San Francisco to finish her journalism degree and Garrett stays behind in New York to work in the music industry, they gamely keep the romance alive with…
19
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"…
20
Private Parts (1997)
★ 6.5/10
The life and career of shock-jock superstar Howard Stern is recounted from his humble beginnings to his view from the top. Possessing a desire to be an on-air personality since childhood, Stern meanders through the…