Drew Barrymore and Leelee Sobieski in Never Been Kissed (1999)

Drew Barrymore, Giuseppe Andrews, and Leelee Sobieski in Never Been Kissed (1999)

Leelee Sobieski and Bryan Brendle in Drop Dead Diva (2009)

Leelee Sobieski and Harold House Moore in NYC 22 (2012)

Adam Goldberg, Leelee Sobieski, Terry Kinney, Judy Marte, Felix Solis, Harold House Moore, and Tom Reed in NYC 22 (2012)

Stellan Skarsgård and Leelee Sobieski in The Glass House (2001)

Leelee Sobieski in The Glass House (2001)

Leelee Sobieski and Trevor Morgan in The Glass House (2001)

Steve Zahn, Leelee Sobieski, and Paul Walker in Joy Ride (2001)

Diane Lane, Stellan Skarsgård, Leelee Sobieski, and Trevor Morgan in The Glass House (2001)

Chris Klein and Leelee Sobieski in Here on Earth (2000)

Albert Brooks and Leelee Sobieski in My First Mister (2001)

Josh Hartnett, Chris Klein, and Leelee Sobieski in Here on Earth (2000)

Leelee Sobieski in My First Mister (2001)

Leelee Sobieski in In a Dark Place (2006)

Timothy Hutton, David Strathairn, Leelee Sobieski, and Anthony Mackie in Heavens Fall (2006)