Sobieski achieved recognition in her mid-teens for her performance in the 1998 film Deep Impact. She received an Emmy nomination for the 1999 TV movie Joan of Arc, and two Golden Globe nominations for Joan of Arc and the 2001 TV movie Uprising.
Sobieski was spotted by a talent scout who noticed her while he was scouting the cafeteria of a New York City private school. 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 a major role in the comedy feature film Jungle 2 Jungle, with Tim Allen. In the film, she played the daughter of Martin Short's character.
She rose to fame in her mid-teens with her appearance in the movie Deep Impact (1998). The film was a major financial success, grossing over $349 million worldwide on a $75 million production budget. Deep Impact brought her to the attention of many casting directors. That same year Sobieski appeared in the Merchant Ivory film A Soldier's Daughter Never Cries.
Sobieski's performance received praise from the critics; Emanuel Levy of Variety wrote that "the graceful Sobieski registers strongly as a potential star, combining physical charm with technical skill." The film also garnered her a Young Artist Award nomination, as well as a nomination by the Chicago Film Critics Association.
In 1999, she was cast as a supporting role in the teen comedy feature Never Been Kissed, which was starring Drew Barrymore. Sobieski also 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".
The title role in the TV movie Joan of Arc (1999) earned her an Emmy nomination and a Golden Globe nomination, and she became the youngest actress ever to portray Joan of Arc in a movie. She received a second nomination for a Golden Globe for her portrayal of Tosia Altman in the 2001 TV movie Uprising. In 2000, Sobieski was a part of the cast of the film Here on Earth, for which she received a Teen Choice Award nomination.
In 2001, Sobieski played the lead role in the road horror film Joy Ride with Paul Walker and Steve Zahn. The film received several favorable reviews. Garth Franklin of Dark Horizons stated that Sobieski "does a better job than usual". That same year, she was cast in the thriller The Glass House, in which she appeared alongside Diane Lane. The film was panned by critics, and had a disappointing weekend $5,738,448 gross with little promotion.
My First Mister, a low-budget drama, was also released in 2001. Sobieski's performance in the film was praised by critics, with Pete Croatto of Filmcritic.com writing that "As for Sobieski, who I've always liked, she does another fine job. This time it's with a shaky character – the troubled Goth chick", and "Sobieski finds her character's human touch and runs with it."
Sobieski landed a starring role in the independent film L'Idole (2002), which opened at the Toronto International Film Festival. She then starred alongside John Cusack in the drama feature Max. She portrayed the character of Cecile in the miniseries Les Liaisons dangereuses (2003) with Catherine Deneuve and Rupert Everett, an adaptation of Laclos's classic novel of sexual intrigue made use of her fluency in French. She portrayed the role of Daneira in Hercules, a television miniseries which was premiered on May 15, 2005.
In May 2006, the experimental-indie film Lying, in which Sobieski starred alongside Chloë Sevigny and Jena Malone, was released. The film premiered at the 2006 Cannes Film Festival and had a limited release in the United States in 2008.
She starred in the American drama Heavens Fall as one of the young women that accuse nine black youths of rape in the segregated South. That same year, she appeared in the horror films In a Dark Place and The Wicker Man, a movie starring Nicolas Cage, which was a remake of the 1973 film of the same title. It was not well received by critics with the New York Times stating that the movie "is neither haunting nor amusing; just boring."
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