After appearing in the musical, she contacted an agent and began taking acting lessons.
Her onscreen acting career began at age 12, in a 1993 episode of the television series Dr.
During her period as a teen idol, she was described as "one of America's favorite 15-year-olds", and "the proverbial girl next door".
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In January 2013, according to TMZ, Oleynik was granted a restraining order against one of her fans, who she claims was so obsessed he changed his last name to hers, as well as leaving gifts for her at her mother's apartment.
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She won the role of Alex Mack over 400 other aspirants.
The series ran on Nickelodeon from 1994 to 1998 and was one of the network's top three most watched shows, becoming quite a favorite among the child and teen audiences and turning Oleynik into a teen idol.
She is known for starring in the title role of the children's television series The Secret World of Alex Mack during the mid-1990s.
She has also appeared in theatrical films, including The Baby-Sitters Club and 10 Things I Hate About You.
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.
As her acting career flourished, she would "divide her time between normal childhood experiences in Northern California and auditions in Los Angeles."Oleynik began acting in a San Francisco production of Les Misérables in 1989 after seeing an audition ad in a newspaper when she was eight years old.
She obtained two parts in the production (young Cossette and young Eponine), both with singing roles.
The film was released in April 1999 and did fairly well at the box office, grossing a total of million domestically.