August sees the release of Marielle Heller's film adaptation of The Diary of a Teenage Girl, a coming-of-age film that follows 15-year-old Minnie Goetze (played by British actress Bel Powley) on an exhilirating exploration of sex that takes off after her first intimate encounter with her mother's boyfriend.

Just last week, the film was slapped with an 18 rating, causing outrage amongst filmmakers and the press alike. As the film’s protagonist comes of age amongst the counterculture of 1970s San Francisco, The Diary of a Teenage Girl reminds us just how important an unapologetic and honest portrait of those awkward years is.

Sticking two fingers up to the ratings board, we recall some of the raunchiest teens in film history, from complicated love triangles in The Dreamers (2003) to virgin collectors in Cruel Intentions (1999) – here’s ten of the best.

KATHRYN IN CRUEL INTENTIONS (1999)

“The Marcia-fucking-Brady of the Upper East Side”: Kathryn Merteuil (Sarah Michelle Gellar) and her promiscous stepbrother Sebastian Valmont (Ryan Phillippe) are two Upper East Side teens living and feeding on nothing but daddy's money, sex, coke and virgins. Sebastian sets off on his biggest conquest yet – to take Annette Hargrove's virginity. Kathryn, meanwhile, attempts to ruin the young Cecile Caldwell (Selma Blair) – the girl who her last lover left her for. Expect manipulation, betrayal and a pretty intense make-out sesh in the park.

BENJAMIN IN THE GRADUATE (1967)

Dustin Hoffman plays graduate Benjamin Braddock in a film that depicts an awkward and unprecented love triangle with the most illustrious Milf in film history. Benjamin is lured into the arms of Mrs Robinson (Anne Bancroft) for sex but is only able to form a meaningful and emotional relationship with her daughter Elaine (Katherine Ross). A sucker for temptation, Benjamin is forced to face the consequences of his fleeting romance with Mrs R, inevitably facing her jealous wrath.

ISABELLE IN JEUNE & JOLIE (2013) 

Jeune & Jolie (Young & Beautiful) is a sexually charged film based on the exploits of 17-year-old stone-cold fox Isabelle. After losing her virginity on a family holiday, she begins a double-life as a teenage prostitute, then throughout the entire film, appears blase and unfazed by all of her sexual encounters until she comes across a much older, married client. After several appointments with her new sugar daddy, she is left panic-stricken when something goes terribly wrong. 

TELLY IN KIDS (1995)

Before you watch The Diary of a Teenage Girl you should really catch up with Larry Clark's infamous Kids. If you want controversy, Clark's cult 90s flick has it all: underage sex, orgies, drugs, booze and STDs. With a character like 16-year-old Telly (Leo Fitzpatrick) – a ‘collector of virgins’, with some of his sexual encounters involving partners as young as 12 – it’s no wonder the film caused such a stir on its release, with many slamming it as glorified child pornography. However, it was also praised for its poignant and confrontational depiction of teen culture, touching on the rising pandemic of HIV/Aids in the 90s.

MATTHEW IN THE DREAMERS (2003)

American student Matthew (Michael Pitt) goes on an indefinite trip to Paris during the 1968 student riots, whereupon meeting enigmatic twins Theo (Louis Garrel) and Isabelle (Eva Green), the three become close friends and move in together. The siblings' incestual relationship comes to light when, during a game of trivia between the trio, Isabelle forces Theo to masturbate to his poster of Marlene Dietrich. One debasing act leads to another, and Matthew finds himself having sex with Isabelle on the kitchen floor, taking her virginity.

GARY IN THE LAST AMERICAN VIRGIN (1982)

Before Jim in American Pie (1999), there was Gary (Lawrence Monoson) in The Last American Virgin, the pizza guy who tries to pick up girls with a little sweet-'n'-low. The determined deflowering of a virgin by a jock and the delivery scene involving a sexy older woman who wants more than just a pepperoni pie become stock scenes for teen sex comedies and pornos alike.

LUX IN THE VIRGIN SUICIDES (1999)

Five teenage sisters live under the strict religious rules of their Catholic parents in a small surburban town where, inevitably, the girls slowly sink into deep despair and isolation. Lux (Kirsten Dunst) loses her virginity to heartthrob Trip Fontaine (Josh Hartnett) before he leaves her on a football pitch on the night of prom. A combination of heartbreak and Lux’s lust for men turns her to having one-night stands on the roof of her parents' house, trading sexual favours for flattery – of course, all watched by the pre-adolescent neighbours next door.

ADÈLE IN BLUE IS THE WARMEST COLOUR (2013)

In 2013, Abdellatif Kechiche released his groundbreaking film based on the same-sex relationship between 15-year-old Adèle (Adèle Exarchopoulos) and older graduating student Emma (Lèa Seydoux). Feeling sexually unfulfilled with a male classmate, Adèle begins to experiment with her sexuality, visiting gay clubs where she meets the blue-haired Emma. Older, creative and self-assured as she is, Emma becomes Adèle's sexual guide and lover, turning Blue is the Warmest Colour into one of the most controversial Cannes winners in recent years.

BRANDY IN THE TO DO LIST (2013)

It’s not often you come across an American comedy film based on a high school girl planning to lose her virginity. The To Do List is a funny and refreshing film depicting the pressures of being a female virgin at college. Orderly as she is, Brandy (Aubrey Plaza) produces a list of things to do before she starts college, with the ultimate goal being to achieve an orgasm. 

ALMA IN TURN ME ON, DAMMIT! (2011)

Parallels can be drawn between this Norwegian comedy and The Diary of a Teenage Girl. Both films focus on a 15-year-old female, her hormones, fantasies and sexual awakening. Alma (Helene Bergsholm), the main protagonist enjoys phone sex, masturbating in random rooms and dirty daydreams. Alma's schoolmate, Arthur (Matias Myren), is central to her sexual fantasies, and after several sessions of self-gratification in other people’s bathrooms, she and Arthur eventually have “sex until the sunrise” in her mother's bed. Kinky.