After this chance encounter, she became a candidate for the role of Claudia in Interview with the Vampire (which she eventually lost out to Kirsten Dunst). Still, the discovery led to other roles in some smaller movies such as Tim Allens mindless Disney dribble, Jungle 2 Jungle and eventually to her first big break in 1998's awful apocalyptic epic Deep Impact, opposite Lord of the Rings star, Elijah Wood.

She next landed the role of Joan in the CBS miniseries, Joan of Arc, which garnered her Golden Globe and Emmy nominations (not bad for a then 17-year-old). While filming J of A in the Czech Republic, she made up for the loss of working with Tom Cruise in Interview with the Vampire to land the role with Tom, Nicole, and a little director named Stanley Kubrick, in the legendary director's last film, Eyes Wide Shut.

Leelee was officially a star with a dedicated following. She went on to star with Drew Barrymore in the eternal chick flick, Never Been Kissed, in 1999, Here on Earth in 2000, and four films in 2001 including The Glass House and Joy Ride. Leelee has several projects in the works and in the can including Hoffman, and Samantha Lang's L'Idole. With a full plate of work ahead and a dedicated fan base, Leelee is sure to be around for a while (and maybe people will even stop mentioning Helen Hunt in every piece about her).

Because of her resemblance to actress Helen Hunt, they were both pitted against each other on the 59th episode of the satirical claymation television series, Celebrity Deathmatch.

Nine Days released a song "Leelee" in tribute to Sobieski.

In the song "Wonder (If She'll Get It)" by Superchic[k], Sobieski and one of her movies, "Here on Earth", were mentioned.