Unnecessary Debate: SHOULD Leo Have an Oscar?

“I must know the answer, Brian.” Relax, Leo. We’ll get there. (via)


Since Matthew McConaughey snatched Best Actor from Leonardo DiCaprio’s hands in early March, many have cried foul at the latter’s lack of a statuette. He has proven to be a heartthrob and an immensely talented actor for two decades now, but does he deserve to be among the ranks of Oscar winners, people like Three 6 Mafia? This debate will be short and sweet and to the point, and will probably be rendered useless at some point in the not too distant future, as long as Leo keeps churning out high-level work. We will consider both his nominated roles and roles that perhaps should have cracked the field. To it, let’s get!


Nominated Roles

Let’s go backwards. Most recently, Leo was nominated as a lead actor for The Wolf of Wall Street, and he also earned a nod for Best Picture as a producer on the film. In the acting race, McConaughey earned his win with a tantalizing role in Dallas Buyers Club. Leo showed wonderful boldness in stepping outside the comfort of A-lister predictability, and he would have won in a lot of years; it just wasn’t enough to overcomethe McConaissance. With regard to the Best Picture race, you’ll recall my fantastic predictions and thoughts…maybe. Not to take anything away from 12 Years a Slave, but I would have loved to see the Academy reward the freshness of Scorsese’s loud work. Regardless, it still would not have felt like a victory for Leo himself, so no matter!

Before those nominations, Leo had not graced the Best Actor field since 2007, when he was nominated for Blood Diamond. That was a fascinating year for DiCaprio, as The Departed took home the night’s big prize while he was left empty-handed individually. In my humble, biased world, I would have liked to see a Supporting Actor nomination for Leo for The Departed, but his lead actor nomination coupled with Mark Wahlberg representing The Departed in the secondary race made this unlikely. He was great in Blood Diamond, but Forest Whitaker had a stronghold on the trophy after an overpowering turn in The Last King of Scotland. Alan Arkin really didn’t deserve the supporting victory, but Leo never had the chance to take that one from him.


Here’s Leo trying to sneak up on an Oscar. (via)


Two years prior, Leo garnered a nomination for playing Howard Hughes in The Aviator. In my mind, this may be the weakest of his nominated roles. I won’t go as far as to say he did not deserve the recognition, but there’s no real way to argue he earned a victory. Jamie Foxx embodied Ray Charles in Ray and won, and Don Cheadle and Johnny Depp would also have been reasonable choices ahead of Leo, for Hotel Rwanda and Finding Neverland, respectively. He fought hard to get this movie made, and it produced his first nomination in the primary acting category, but it didn’t deserve to be anything more than an introduction to the race.

Leo’s only Supporting Actor nomination was also his first Oscar nomination, in 1994 for his performance in What’s Eating Gilbert Grape. This may seem like only an early feather in his well-decorated cap, but his performance was magnificent and does spark some debate twenty years later. Tommy Lee Jones beat out DiCaprio and the rest of the competition for his role in The Fugitive, with which I have no beef (link), but Leo’s performance was arguably deserving of a victory. Problems arise, however, when one considers the other nominees that lost out, which only seems fair. John Malkovich and Pete Postlethwaite gave memorable performances, but above all Ralph Fiennes was absolutely haunting in Schindler’s List as Amon Goeth, a role for which I firmly believe he should have beat out Jones and the rest of the competitors. Thus, I don’t fully agree with these results, but this does not mean Leo got the short end of the proverbial stick.


He showed us his talent very quickly, but he still did not deserve an Academy statuette. (via)


Other Roles

I admit to loving Leo in most of his movies, but even I cannot say there are any other roles for which he deserved to be in serious Oscar contention. The mid-90s brought The Basketball Diaries, Romeo + Juliet, and Titanic, all of which showcased young Leo’s versatility and talent. He bounced from troubled teen to the most famous piece of literature in the world to the most famous piece of overratedness in the world in a matter of months, but these films served mainly to cement his place among Hollywood’s elite rather than among the ranks of other Oscar winners.

Both Gangs of New York and Catch Me If You Can came out in 2002. I personally don’t love Gangs, finding it a bit lower in caliber when compared to Scorsese’s fuller works, but I do have a soft spot for Catch Me If You Can. Leo earned a Golden Globe nomination for the movie but was not in the Oscar race; he very well may have deserved a nomination, but he would have lost out to Adrien Brody’s career-defining performance in The Pianist anyway. Both 2002 movies are highly entertaining because of Leo and other factors, but neither performance deserved much more attention than it received.

He did Gatsby right and didn’t get enough credit, but an Oscar was out of the question. (via)

The last handful of years have brought a handful of acclaimed roles for Leo as well as more generally respected movies.  I already touched on The Departed, but following that there was Revolutionary Road, Inception, Django Unchained, and The Great Gatsby, among others. I was not a huge fan of RR, partially due to its slow, plodding nature and partially due to my inexplicable distaste for Kate Winslet. Inception made for great entertainment and stunning aesthetics, but none of the acting performances stood out above the brain-blasting plot and subplot and super-subplot. I loved Leo in Django, and I would not have been opposed to him receiving a nomination, but Christoph Waltz stole his scenes and earned every bit of his second Oscar for that film. Finally, I thoroughly enjoyed the trippy new incarnation of Gatsby, and I loved Leo as the titular titan of literature, but he probably didn’t deserve any more award attention than he got, and he would have had no shot against himself and McConaughey regardless.



No, Leo should not have an Oscar at this point. I’m confident that he will end up with plenty of hardware to show off to his hot models and acquaintances, but for now his career consists of memorable performances that either weren’t quite Oscar-caliber or came in years when other supremely talented men were more deserving. My love and admiration for Leo still burn bright, and I hope he won’t hold this against me.


It’s ok, buddy. You’ll get one someday. (via)







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About Author: Brian McMahon

Brian is an author and co-founder of GoodWillWatching. He likes to write and is deathly afraid of bugs. His Great American Novel, not yet titled or existent, will be shocking the world some time or another. He once stayed up for two days straight because of poor information regarding the arrival of Halley’s Comet, which was not due for approximately 57 years. You can follow him @bm1313 on Twitter, or in real life from a safe distance.