Question of the Week: Which film(s) do you think Leonardo DiCaprio deserved to win an Oscar for?

Today is Leonardo DiCaprio’s 39th birthday. He’s still got that boyish look despite being a year short of 40! It’s been sixteen years since Titanic catapulted him to a matinee idol, but he’s since gained a movie star status and practically shed the *curse* that plagued a lot of child actors who’ve hit it big before they even hit 25.

LeoWolfofWallStreet
A toast to Leo – he’ll be seen next in The Wolf of Wall Street

I’ve made a tribute to Leo three years ago as part of my Inception countdown post where I listed why I think he’s got what it takes to be called one of Hollywood’s greatest actors working today, on top of being one of the world’s biggest movie stars.

I haven’t made up my list of Top 5 Leonardo DiCaprio movies yet, but I might do that next year. For now, I’m just going to leave it open to discussion amongst moviegoers, particularly on the topic about why DiCaprio still hasn’t won an Oscar to this day despite having been nominated three times.

2007 Nominated
Oscar
Best Performance by an Actor in a Leading Role
Blood Diamond (2006)
2005 Nominated
Oscar
Best Performance by an Actor in a Leading Role
The Aviator (2004)
1994 Nominated
Oscar
Best Actor in a Supporting Role
What’s Eating Gilbert Grape (1993)

My friend Kristin from All Eyes On Screen blog who was in town this weekend and we had a discussion about this (with her fiancee and my husband) as to why Leo’s still empty-handed. Even when his co-star gets nominated or even won, he often got overlooked.

TotalEclipsePosterIt’s almost become a parody how elusive Oscar seems to be for Leo, there are countless articles/tweets/blog posts etc. ruminating why he continually gets snubbed year after year. It’s a shame really as he’s definitely a talented and brave actor. Even in his early work Total Eclipse back in 1995 where he played 19th century French poet Arthur Rimbaud, it was apparent he wasn’t afraid to play daring, unhinged characters. I was quite shocked that he was willing to do full frontal nudity and gay sex with David Thewlis (who played his mentor/lover Paul Verlaine) early in his career. He seems to have a penchant for playing obsessive/neurotic characters, i.e. Howard Hughes (The Aviator), and roles in Shutter Island, J. Edgar, Django Unchained, and last but not least, The Great Gatsby.

As you can see in Nostra’s ‘The Many Faces Of…’ series on Leo, he’s got quite a stellar resume with about 30 feature films under his belt. He may not be the most chameleon-ic actor and he doesn’t bother with adopting a certain accent even when playing non English-speaking characters, perhaps it’s a good idea though given his unconvincing South African accent in Blood Diamond. That said, I still think he’s due for a major award one of these days. Let’s hope he won’t be the Susan Lucci of the Motion Picture industry. Who knows, perhaps Scorsese’s The Wolf of Wall Street will finally be his ticket to Oscar glory!


So my question to you is, which of DiCaprio film(s) have you seen you that warrant him an Oscar nom and/or win?

[Feel free to speculate as to why you think he hasn’t won… that always makes for an interesting discussion ;)]