Most Fashionable Role: The Great Gatsby, 2013
Memorable Movie Quote: “I knew it was a great mistake for a man like me to fall in love…”
The Look: As one of the most tortured and hotly contested characters in literary history, Jay Gatsby is an enigma. Upon first glance, he appears to epitomize everything that is vain and shallow about the 1920′s upper crust. Yet as the character develops, we realize that his innocence and ambition come from a place of deep goodness rather than selfish desires like everyone else in the novel. Leo (we’re clearly on a first-name basis) is the perfect actor to play this conflicted character, himself an innocent boy trapped in a burgeoning man’s body. To me, Leo will always be the young kid with the gorgeous face and swooping hair that I can never have. My solatium, however, is that he revisits that old boyish charm in this role with his pastel suits, slicked-back locks and a self-effacing charm that both the actor and the character often wear as a mask.