I was thinking The Departed...
lost to forest whitaker in last king of scotland...which was the better performance.
lost to jamie fox in ray...which was the better performance.
Lost to Christoph Waltz from Django. If you want to argue Waltz should have been in the best actor category, then yeah I agree Leo should have won here. But since Waltz was placed in this category, he had the best performance therefore shoulda got this award.
Lost to Matt McCauneghey for Dallas Buyers Club. This is a toss up to me. Christian Bale in American Hustle, and Chiwatel Ojifor in 12 years a slave also had amazing performances. The award coulda went to either one of those 4 and I wouldnt have been mad.
Revolutionary Road...He's been killing it for a min
Lost to Sean Penn in Milk. Sean Penn had the better performance. Mickey Rouke in The Wrestler, and Brad Pitt in Benjamin Button were also better performances than Leos in Revolutionary Road.
What's Eating Gilbert Grape
Lost to Tommy Lee Jones in the Fugitive. Definitely bullshyt. Leo shoulda won this award. Ralph Fiennes from Schindlers List got screwed here too. I think they didnt give it to Leo because he was a young, fairly unknown actor and Tommy Lee Jones is like acting royalty. Pure bullshyt award politics.
Leo is only unlucky in the sense that he has been out-shined in the years of his most worthy performances.
an actor of his caliber you would expect to have 3 or so academy awards by now...but if you look at the tape, all of his losses besides 1 were very understandable.
Something else I find interesting...look at Leo's filmography:
http://en.wikipedia.org/wiki/Leonardo_DiCaprio_filmography
Dude probably has the best resume in Hollywood.