Leonardo DiCaprio
Celebrity (Magnolia Productions, Woody Allen, 1998)
Woody Allen had one of his mini-revivals in the mid-90s, but that would all come crashing to earth with this black and white bit of navel-gazing. Leo actually does ok, riffing on his image at the time as both a gifted actor and an over-amorous enfant terrible but still, for an actor who has been scrupulously careful in his selection of roles, this one stands out as the black mark.
