she was close to. After The Secret World of Alex Mack ended its run, Oleynik had a starring role in the film 10 Things I Hate About You as Bianca. The film was released in April 1999, and did fairly well at the box office, grossing a total of $38 million domestically. From 1998 to 2000, Oleynik appeared in twenty-one episodes of the NBC series 3rd Rock from the Sun as Alissa Strudwick. During 2000, she also appeared in two independent films: 100 Girls (opposite Emmanuelle Chriqui, Katherine Heigl and Jonathan Tucker) and A Time for Dancing (opposite Shiri Appleby); neither film received a theatrical release in the United States. Oleynik had a supporting role in the independent drama film An American Rhapsody (2001), opposite Nastassja Kinski and Scarlett Johansson, which follows a young woman whose parents are forced to leave her behind in Communist Hungary while they flee to the United States. 2003–present Oleynik had a supporting part in Bringing Rain (2003), a low-budget teen drama starring Adrian Grenier and Paz de la Huerta, which premiered at the Tribeca Film Festival. In 2005, she appeared as a guest star on the series Malcolm in the Middle as Reese's lesbian army buddy who develops a crush on his mother. Oleynik was cast in a supporting role in the series Pepper Dennis, which began airing on The WB in April 2006, but was not picked up by The WB's successor The CW. The same year, she starred in the independent drama Pope Dreams. In March 2008, Oleynik guest-starred in episode 13 of Aliens in America. In 2009, she provided audio commentary for the 10 Things I Hate About You 10th Anniversary Edition Blu-ray. In March 2011, Oleynik started appearing in a recurring role on Hawaii Five-0 as CIA analyst Jenna Kaye, until her character was later killed off. She was subsequently cast in the Ayn Rand adaptation Atlas Shrugged: Part II (2012), as Cherryl Brooks, a store clerk who becomes acquainted with the protagonist, Dagny Taggart (portrayed by Samantha Mathis). John Tammy of Forbes praised it as a "must-see" film. Oleynik also guest-starred as Ken Cosgrove's girlfriend (and later wife) Cynthia Baxter in several episodes on the AMC television series Mad Men. In 2016, Oleynik starred in the one-woman show I Loved, I Lost, I Made Spaghetti at the Hangar Theatre in Ithaca, New York. Beginning in 2017, Oleynik starred in