Clyde Barrow

Clyde Barrow and Bonnie Parker -- better known as the outlaws Bonnie and Clyde -- pose for a photo sometime between 1932 and 1934.  The duo were ambushed and killed by law officers on 23 May 1934.

Photo from the New York World-Telegram and the Sun Newspaper Photograph Collection in the U.S. Library of Congress, reprinted via Wikipedia.