After roles in the popular thrillers I Know What You Did Last Summer and Scream 2 (both 1997), Sarah Michelle Gellar starred in the 1999 films Simply Irresistible, a romantic comedy, and Cruel Intentions, a modern-day retelling of Les Liaisons Dangereuses. Cruel Intentions, with a kiss between Sarah Michelle Gellar and co-star Selma Blair that won the two the "Best Kiss" award at the 2000 MTV Movie Awards, was a modest hit at the box office. Critic Roger Ebert stated that Gellar and co-star Ryan Phillippe "develop a convincing emotional charge" and that Sarah Michelle Gellar is "effective as a bright girl who knows exactly how to use her act as a tramp"
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