Sobieski was first noticed by a talent scout in the cafeteria of a New York City private school. That encounter led to her audition for the role of Claudia in "Interview with the Vampire" (1994), a role which ultimately went to Kirsten Dunst. Sobieski portrayed the character of Anna Yates in the 1994 TV movie "Reunion" starring Marlo Thomas. Next, she played a lead role in "A Horse for Danny", a 1995 made-for-television film. In 1997, she snagged her first role in a studio film playing the daughter of Martin Short's character in the Tim Allen comedy "Jungle 2 Jungle". In 1999, Sobieski appeared in Stanley Kubrick's "Eyes Wide Shut". Recalling acting alongside Tom Cruise, Sobieski stated he was "very kind and considerate with me," and says her most vivid recollection of Stanley Kubrick was that he "genuinely seemed to hold something magic".