4. The Aviator (2004)
If anything this was more Academy baiting than Gilbert Grape, mental difficulties, a celebrated historical figure and directed by Martin Scorsese this should have bagged Leo his Best Actor Award. It won him a Golden Globe just a few weeks previous and won Cate Blanchett a Best Supporting Actress award for what was probably an inferior turn than Leo, who encapsulated the role of Howard Hughes and kept him captivating for an incredibly long run time. You dont feel it when watching a brilliant movie that probably should have garnered him his win. Sadly he lost to Jamie Foxx in Ray, which had the advantage of being about a celebrated historical figure, blindness and drug abuse. One point short Leo.