The Curious Career Arc Of Leonardo DiCaprio In The Eyes Of The 21st Century American Male


Imagine Justin Bieber as your favorite singer a decade from now, or JaMarcus Russell as a Hall of Fame Quarterback, or Kim Kardashian as an Oscar winning actress with successful relationships and a preference for solidarity, free from the public eye. If you were a boy in 2006, predicting that Leonardo DiCaprio would one day be in some of the best and beloved movies of our generation would have been equally preposterous. Leo was a punchline, an insult thrown at the less fortunate, an eye roll-inspiring teen heartthrob who proclaimed himself “King of the World,” with no hope of being anything but a jester in the eyes of the American male. Now, Leonardo DiCaprio is my favorite actor, and the transition was as remarkable as the realization.

Like most 20-somethings, I was introduced to Leonardo DiCaprio because of Titanic, and like most 20-something males, I thought he was awful. Sure, Leo had gotten his start in TV show guest spots on Roseanne and Growing Pains. Sure, he had been in some movies that I have since went back and watched, such as highschool classroom staple What’s Eating Gilbert Grape, an incredible performance in a mediocre movie The Basketball Diaries, and the odd 90’s beach themed Romeo and Juliet. Titanic made DiCaprio a household name. However, as girls swooned over his golden locks and boyish face the growing ire of elementary school boys surged.

Perhaps it was us revolting against, as boys, what every girl seemed to want. Perhaps it was jealousy as we sped toward puberty ourselves. Perhaps it was the idea that Leo was deemed “gay” by our peers, back when that was a socially acceptable and near-impossible to overcome insult that shunned all adoration in fear of association. Similar to Pokemon, you may have liked Leo at the time, but there was no chance you admitted it.

I was 15 when Gangs of New York came out, and had I watched it then the disdain would have undoubtedly ended there. Gangs of New York is one of my all-time favorite films and an absolute tour de force for both Leo and Daniel Day-Lewis. But by 2002, DiCaprio had slipped into pop culture irrelevancy, and while I distinctly remember seeing previews for The Aviator two years later, I also definitely remember brushing it off with a, “Oh look, Leo’s trying to be a serious actor,” dismissal.

2006 changed everything. The Departed brought not only a perfect late-night drunken freshman-year anthem in the form of the Dropkick Murphys’ “I’m Shipping Up to Boston,” but also delivered Leonardo DiCaprio back to relevancy among American males. His turn as a cop undercover in the mob was as good as his South Boston accent, and the range of emotion he displayed was outstanding. It helped too that the movie was awesome, full of more betrayal and star power than most. Then, right after, Leo starred in Blood Diamond, perhaps an even better movie than The Departed. Again, he nailed the accent, perfected the character, and led us on the whirlwind tour of an immoral ex soldier in search of a priceless gem who is redeemed by the end.

By now I had seen Gangs of New York as well and I had come to the realization that Leonardi DiCaprio, he of Titanic scorn, he of baby-faced derision, was in three of my favorite movies to date. Could he actually be one of my favorite actors? Could he have made a celebrity perception turnaround, the likes of which have never been as dramatic or profound? Justin Timberlake was never at the depths of DiCaprio. Other heartthrobs never achieved Leo’s terrific modern rise.

Of course, since then, DiCaprio has been unstoppable. 2010’s Shutter Island was intriguing and fun, despite an eye-rolling twist at the end. Inception was fantastic and original. His racist plantation owner role in Django Unchained was terrific. Without his eerie-good performance as the titular character, The Great Gatsby wouldn’t have been anything. Now, with The Wolf of Wall Street coming out in November, the movie promises to join the upper echelons of both Leo’s movies and my movies of choice, if the book and the trailer are any indication. If DiCaprio does anything, he delivers. He has joined the ranks with Daniel Craig, Hugh Jackman, Al Pacino, Daniel Day-Lewis, Brad Pitt, Denzel Washington, Ryan Gosling, and a host of others as actors whose movies I will always see, regardless of the quality or content. In fact, he has surpassed them all.

It begs the question why I and countless others even disliked him in the first place. Was it the rampant put-on homophobia of the 90’s? Was it the idea that a baby faced blonde guy was more desirable to girls my age than dark-haired, started-shaving-at-12, me? Was it because the only good part of Titanic was the ship breaking in half and then sinking into the ocean, and my pop culture resentment for the most overrated song and movie of all time was focused away from James Cameron’s direction and Kate Winslet’s impeccable breasts onto the easiest target? Whatever the reason, the contempt for Leo was buried like this pop culture obsession with vampires and zombies needs to be.

It makes me wonder who in today’s celebrity bubble will make the transition from disparaged to respected; which person we shake our heads at now only to promote in a decade’s time. DiCaprio’s reputation among American boys and men may have drowned in the Northern Atlantic for a time, but his ascension from derision to celebration grew alongside his ability to grow facial hair and he is now, without question, the actor I most enjoy watching.

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I used to write for TFM and PGP when they were funny.

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