Sobieski was spotted by a talent scout who noticed her while he was scouting the cafeteria of a New York City private school as part of a recreational visit. After that encounter, she became a candidate for the role of Claudia in Interview with the Vampire (1994), which she eventually lost out to Kirsten Dunst. She portrayed the character of Anna Yates in the 1994 TV movie Reunion, which starred Marlo Thomas. Next, she played a lead role in A Horse for Danny, a made-for-television film which was released in 1995. Later, she had her first role in a studio film, as Martin Short's character daughter in the Tim Allen comedy Jungle 2 Jungle. In 1999, Sobieski played a modern Lolita in Stanley Kubrick's Eyes Wide Shut. The film opened to generally positive reviews, but it generated several censorship controversies due to the explicit nature of its sex scenes. Recalling acting alongside Tom Cruise, she said 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".
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