Reese Witherspoon is widely regarded as one of Hollywood's most likeable stars, having built a career on roles that showcase warmth and versatility, from Pleasantville to Walk the Line and Wild. Yet she has revealed that this same likeability made it unusually difficult to portray Annette Hargrove, her buttoned-up character in the 1999 teen drama Cruel Intentions, since audiences were far more drawn to the film's manipulative and morally dubious characters played by Sarah Michelle Gellar and Ryan Phillippe.

Speaking to The Guardian around the film's release, Witherspoon explained that she deliberately reworked Annette, who was adapted from Madame de Tourvel in the 1782 novel Les Liaisons dangereuses, away from a shy and timid original conception into a more intellectual, principled and strong-minded figure to make her feel contemporary and realistic. Ironically, those very traits, which have endeared Witherspoon to audiences in real life, made it harder for viewers to warm to Annette on screen, especially when set against her "wonderfully despicable" co-stars.