Quick Links Vanilla Sky Exists Between Dreams and Reality Tom Cruise's 1999 Erotic Thriller Is an Excellent Companion Piece to Vanilla Sky Vanilla Sky Has to Be Seen More Than Once

Tom Cruise has consistently shown a willingness throughout his career to apply his stardom to challenging projects and roles, beginning with his Oscar-worthy performance as Vietnam veteran Ron Kovic in the 1989 biographical drama film Born on the Fourth of July. With his performances as misogynistic dating guru Frank T.J. Mackey in the 1999 drama film Magnolia and cold-blooded assassin Vincent in the 2004 thriller film Collateral, Cruise also proved that he was unafraid to subvert audience expectations by playing unsympathetic characters.

This ambitious career approach is perhaps most clearly embodied in the 2001 psychological thriller film Vanilla Sky, in which Cruise plays a hedonistic New York playboy whose carefree lifestyle, along with his sense of reality, is completely upended after his handsome character,...