Poor, sweet Leo! Not only did he sink to the bottom of the ocean in Titanic, but he's also never won an Oscar after four nominations. He was first nominated at the tender age of 19 for his role as the mentally handicapped Arnie Grape in What's Eating Gilbert Grape. He also snagged two Best Actor noms for 2004's The Aviator and 2006's Blood Diamond. He's up again in 2014 for his tireless performance in The Wolf of Wall Street, but all signs point to Matthew McConaughey snagging this year's win.