In 1997, Paulson made her feature film debut in the independent thriller film Levitation, playing a woman who discovers she is pregnant after an anonymous sexual encounter. Leonard Klady of Variety noted that Paulson and her co-stars are "not supported by the script," concluding: "Levitation is a grim, convoluted saga of identity and belonging. An ill-fitting combination of melodrama and magic realism, the indie effort will have a decidedly difficult time in the theatrical arena. " She also appeared Off-Broadway in a fall 1998 production of Killer Joe. She subsequently played Elisa Cronkite in The WB comedy-drama series Jack & Jill (1999). The same year, she was also cast opposite Juliette Lewis and Diane Keaton in the drama The Other Sister, playing the lesbian sister of a developmentally-disabled woman in San Francisco, and in a supporting part playing a hostage in the comedy Held Up, opposite Jamie Foxx. The following year, she had a small supporting role in the comedy What Women Want, starring Mel Gibson and Helen Hunt.