37. 'Vanilla Sky' (2001)
It seemed as if Cameron Crowe had cracked the code on reinventing Cruise with his 1996 romcom hit Jerry Maguire (see No. 8). But then this remake of the 1997 Spanish thriller Open Your Eyes happened. Cruise plays an obnoxious, rich publisher whose romantic callowness leads one of his lovers (Cameron Diaz) to drive the car they're in off a bridge. Post-accident, our disfigured hero begins to see and experience things that blur the lines between fantasy and reality. Cruise himself seems oddly detached and unconvincing – you'd think he'd nail the entitled jerk part, at the very least, but nope. This film has attracted a cult following since its initial release, but it's far from the star's finest hour.