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When a wealthy rockstar is brutally murdered, a police detective finds himself in a torrid affair with the prime suspect—Sharon Stone clocking in one of many career highs as a crime novelist. Over the course of the three decades that she has spent in front of the camera, Reese Witherspoon has delivered many memorable performances, but her role in this teen drama served as a career-defining moment.

Often credited with seducing an entire generation, Cruel Intentions brings Dangerous Liaisons to the doorstep of an elite Manhattan prep school. A wager between two scheming step-siblings, played by Ryan Phillippe and Sarah Michelle Gellar, is derailed when Phillippe falls for the headmaster's abstinent daughter—played by his then-girlfriend, Witherspoon. The movie follows the picture-perfect life of a gallerist, which eventually begins to unravel as she embarks on a string of one-night stands and affairs.

After many casting changes that invited an impassioned response by its cult-like fandom, Jamie Dornan finally stepped into the titular grey suit with Dakota Johnson taking on the role of literature student, Anastasia Steele. A chance interview leads to her sexual awakening over the course of three movies, as Christian Grey educates her on the ways of BDSM. Follow up that late-night You marathon with this thriller, which casts Jennifer Lopez as a recently-separated high school teacher who finds herself falling for the charms of a teenaged boy next door, played by Ryan Guzman.

Things take a dark turn after a passionate one-night stand, when his violent past and obsessive behaviour comes to light. A devoted family man left alone for the weekend finds himself giving in to temptation when two girls knock on his door for help. Dire consequences follow as the girls proceed to make him pay for his infidelity by holding him hostage.