A developmentally disabled  midwestern boy.  A record-breaking aviator. A Rhodesian diamond smuggler. A market manipulating- stockbroker.

These were characters portrayed by actor Leonardo DiCaprio so well that he received Academy Award nominations for all of  them… but never received a win for any of them.

For years Leonardo DiCaprio sat in his chair as they announced the nominees for best actor, waiting to hear his name called and to approach the stage to give a speech he diligently prepared. All four years, however, DiCaprio remained sitting, having to use his acting skills to put on a face of graciousness for the winner who was often someone who never even attended an Academy Award ceremony before. After seeing him lose for the fourth time despite being nominated since he was a teen I wonder to myself “Why? Why can’t he win just one award? Just one!”

Sometimes, I wonder if the Academy does this to him on purpose,  perhaps to mold him into this generation’s Peter O’Toole. Peter O’Toole was nominated eight times for best actor without winning once. Toward the end of his career, the Academy gave him an honorary award, to which he reacted bitterly, believing that he could still win one on his own. Looking at O’Toole’s career and DiCaprio’s, I wonder if the Academy is setting Leo up to be our generation’s O’Toole.

The main reason I had such a thought was not so much due to how many times they’ve been nominated and lost as much as because the fashion in which they lost. For both actors, there was one time where they were nominated and truly deserved to win. For O’Toole, it was his role in “Lawrence of Arabia” that should have gotten him the win. However, he lost to Gregory Peck from To Kill A Mockingbird. Having seen both films, I found it baffling that O’Toole’s Lawrence lost to a Peck’s Atticus Finch. Don’t get me wrong, I thought Peck played Finch well, and I have immense respect for him, but O’Toole truly had one of the best performances of all time (I know I Kanye’d there, and I apologize). For the rest of the nominations, O’Toole’s performances were adequate enough for him to be nominated, but there was always someone better. For instance, when his performance in Venus was nominated, he rightfully lost to Forrest Whitaker from “The Last King of Scotland.” After seeing both of these movies, I can definitely justify his loss, for while I thought O’Toole was remarkable in Venus despite his old age, Whitaker made the terrible Idi Amin come to life. For all but one nomination, O’Toole performed well enough to be at the Oscars, but there was always someone better.

Now as for DiCaprio, the role for which he should have won was in “The Wolf of Wall Street,” where he played stockbroker Jordan Belfort. He was able to capture the ambition, the arrogance and the vulnerability of such a bold and dynamic character. While I admit Matthew McConaughey, the eventual winner, played his role to a tee and also deserved to win an oscar for that role, I felt that DiCaprio had a slight edge on him by having more power in his role. However, his other nominations(“Gilbert Grape,” “Aviator,” “Blood Diamond”) were always compared to someone who truly separated themselves from the competition such as Tommy Lee Jones, Jamie Foxx and Whitaker who in the same year and at the same time, beat Dicaprio and O’Toole with his role in The Last King of Scotland, completely trolling both of them.

While their histories at the Oscars are incredibly similar, there is one major difference between the two, and that is the future.

While O’Toole unfortunately passed away in 2013, Leo is only 41 and has many years ahead of him. On top of that, his role in the 2015 hit “The Revenant” as the stranded frontiersman Hugh Glass is nominated for an Oscar, and in my opinion, it is his best role to date. I wish him the best of luck this Sunday, and I hope he can win it and dispel this notion that he will not win an Academy Award until the Academy feels bad for him and gives him one out of pity when he turns old.