49. Leelee Sobieski
Worst Performances: The Glass House (2001), The Wicker Man (2006), In the Name of the King: A Dungeon Siege Tale (2007), 88 Minutes (2008), Branded (2012)
At one time, circa 1999, Leelee Sobieski seemed to be at the forefront of her generation, having done fine work in Stanley Kubrick's Eyes Wide Shut and co-starred in a respectable, critically appreciated genre flick (Joy Ride). But then 2001's The Glass House happened, proving that Sobieski wasn't exactly leading lady material, and then things got even worse. Through embarrassing project choices like The Wicker Man and In the Name of the King: A Dungeon Siege, the once-promising actress' stock plummeted. Her performances in those flops certainly didn't help.