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She was born in Santa Clara County, California, to Lorraine (Allen), a nurse, and Roman Oleynik, an anesthesiologist. Her paternal grandfather, Josephy Oleynik, was born in Pokdamin, Ukraine.Her paternal grandmother, Anna Cherpak, was of Ukrainian/Rusyn descent.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.
In 2009, she provided audio commentary for the 10 Things I Hate About You 10th Anniversary Edition Blu-ray.Rather than try to explain things, she would quickly glance around, then tell them "Not here - everybody would see! Oleynik reprised the role in an All That sketch, although the name was changed to "Alex Sax".Oleynik later appeared in the 100th episode of All That.Later in 1993, she was subsequently cast in the lead role of the series The Secret World of Alex Mack where she portrayed a teenage girl who receives telekinetic powers as the result of an accident.
She won the role of Alex Mack over 400 other aspirants.Also during her time on The Secret World of Alex Mack, she played one of the lead characters in the 1995 feature film The Baby-Sitters Club (opposite Rachael Leigh Cook and Schuyler Fisk), appeared in several episodes of Boy Meets World, wrote an advice column for Tiger Beat magazine, and was involved in Nickelodeon's The Big Help charity Hands Across Communication, Surfrider Foundation and the Starlight Children's Foundation.