Featuring an army of giant ants doing battle with an army of tawny-skinned, white-toothed young men and women who appeared to have wandered off a Nordic Track commercial, the movie met with enough success to constitute Richards' "big break." She gained further exposure (literally) and fame with her next venture, 1998's Wild Things. Cast as spoiled socialite Kelly Van Ryan, Richards gave a delightfully trashy performance in a film that called for her to lie, cheat, scheme, seduce, kill, and even perform a lesbian love scene with co-star Neve Campbell. The film was successful in its ability to satisfy its audience's desire for tacky and oversexed fun, and it provided Richards with further opportunities, including 1999's Drop Dead Gorgeous.

Co-starring with Kirsten Dunst, Richards played a small-town beauty pageant contestant in a film that gleefully plays with America's beauty ideals, something that was undoubtedly familiar territory for the actress. Though 2001's horror flop Valentine and the straight-to-video Good Advice did little for her career, Richards saw her star rise further in 2002 with a set of high-profile films that did much to expand her range. In director Malcolm D. Lee's cheeky Blaxploitation send-up Undercover Brother, Richards was able to give her evil Wild Things persona an even broader, more satirical spin as White She-Devil, an operative for an evil caucasian conglomerate bent on converting the world to its mayonnaise-eating ways. Richards' intentionally wooden line readings and sly self-parody made her an invaluable part of Brother's comic ensemble, helping the film become a minor hit. The romantic comedy The Third Wheel came later that year.