Selma Blair in Cruel Intentions (1999)

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This Dangerous Liaisons for Generation Next is likable in some parts, unbelievable in others and admirably insane throughout. Better still, it's packed with a nubile cast just bubbling with sensuality. Reese Witherspoon hits upon the perfect mixture of naïveté and sex appeal, and Ryan Phillipe does enough pretty-boy overacting and awkward line readings to wrest the “Himbo” crown away from Keanu Reeves. The Central-Park-set "kissing lesson" between Sarah Michelle Gellar’s rich bitch and Selma Blair’s socially awkward mess of female neuroses also makes this an all-time Sapphic classic.