Last Tango in Paris (1972)
The Franco-Italian romance starring Marlon Brando centered on a couple that conducts an anonymous sexual relationship in an unfurnished apartment in Paris. The film’s portrayal of sexual violence (and the use of butter as a lubricant) sparked controversy, even earning a TIME cover story. Watch here
Risky Business (1983)
Tom Cruise burst onto the movie scene by having sex on an abandoned Chicago “L” train with a call girl as a high schooler in this movie. Watch here
9 1/ 2 Weeks (1986)
This Mickey Rourke and Kim Basinger film featured BDSM long before Fifty Shades ever did. Some of the scenes border on assault, and at one point the couple even has sex after stabbing another man in the buttocks. Watch here
Henry & June (1990)
Henry & June was the first film to receive an NC-17 rating from the MPAA (which had recently replaced an X rating). The movie was based on the real-life sexual relationships among Anais Nin, famed author Henry Miller, and his wife June Miller. Watch here
Basic Instinct (1992)
Sharon Stone’s infamous leg-crossing scene has gone down in cinema history as one of the most provocative shots ever filmed. Watch here
Boogie Nights (1997)
Back when he was still widely known as underwear model Marky Mark, Mark Wahlberg took on the role of a porn star in Paul Thomas Anderson’s matter-of-fact look at the mechanics of porn. Watch here
Eyes Wide Shut (1999)
Stanley Kubrick’s last film, starring real couple Nicole Kidman and Tom Cruise, included several sex scenes (real and fantasy) as well as an orgy scene that had to be altered to earn an R rating for the American release. Watch here
Y Tu Mama También (2001)
Two friends spontaneously decide to engage in a sexual relationship with an older woman while on a road trip. Watch here
Secretary (2002)
Secretary also explores the lines between pleasure and pain. After Maggie Gyllenhaal’s character makes a typing mistake, she’s spanked by her boss played by James Spader (coincidentally also named Mr. Grey). The incident leads to a sadomasochistic relationship between the two. Watch here
Brokeback Mountain (2005)
In 2005, Brokeback Mountain was one of the first mainstream motion pictures to feature a love story and sex scenes between two gay characters played by two famous actors, Heath Ledger and Jake Gyllenhaal. Watch here
Black Swan (2010)
Natalie Portman won an Oscar for her Black Swan role, but what created the most buzz was a hallucinatory sex scene between her and Mila Kunis and a botched-masturbation sequence. Watch here
Nymphomaniac (2013)
The two-part Lars von Trier movie about a self-described nymphomaniac was released in two formats: the original hardcore version, and an edited softcore one. While some dismissed it as porn, most critics embraced the film as an engaging exploration of a woman’s sexuality. Watch here
Blue Is the Warmest Color (2013)
This French romance film made a splash first at the Cannes Film Festival and then in theaters for its explicit lesbian sex scenes between two teenage girls. Watch here
Gone Girl (2014)
Just a few months before Fifty Shades of Grey‘s release, Gone Girl shocked audiences with a brutal and bloody sex scene. Watch here
Fifty Shades of Grey (2015)
Audiences are curious how the popular book filled with BDSM will translate to the big screen. Fandango reports that it has sold more pre-sale tickets for Fifty Shades of Grey than any other R-rated film. Watch here
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