Rose McGowan next took on the starring role of Courtney Shayne in the dark teen comedy Jawbreaker (1999). The role still remains one of Rose’s personal favorites: "I love Courtney Shayne, she was hilarious. She was very misunderstood. People said she was so evil and I say, ‘Well, she was just a sociopath.’” Jawbreaker gained Rose many new fans and an MTV Movie Award nomination for Best Villain. She also had a role as the dead rock goddess Sno Blo in Sleeping Beauties, a short film.

After taking some time off from the movies to be with her fiancé, Rose couldn’t seem to find roles that really challenged her. In 2000 she was seen in supporting roles in Ready to Rumble and The Last Stop. She next had small roles in Monkeybone and The Killing Yard before starring in as the vulnerable and confused Moira Kennedy in Strange Hearts. Although none of these movies were great successes in terms of box office or critical response, they once again proved Rose’s versatility as an actress and her great charisma. "Yep, I have made some bad films”, she admitted. “But unlike Kate Hudson or Gwyneth Paltrow I didn't grow up in Hollywood, with stability and wealth and all my needs were catered to. I came here trying to survive. I couldn't afford to make worthy, artistic movies for no money. I had to pay the rent.”