Leonardo DiCaprio: From Teen Heartthrob To Oscar Winner — Five Stand-Out Moments That Paved The Way To Glory

Leonardo DiCaprio finally won an Oscar.

This will be the headline of the day, and rightly so. Leonardo DiCaprio has graced our screens for nearly 30 years now, and the actor has strived and worked his way into the small echelon of great actors that now define our generation. Many will make light of this — some will call it overdue, some will say he didn’t earn it, and many will say this should have happened much sooner — but one thing is for sure: the win was deserved. For a man who has put his mind, body, and soul into his career to meticulously hone his craft and bring us some of the greatest performances of the last three decades, the Oscar win is just reward for services rendered.

But why did it take so long?

There are many theories on the internet, and many lists with a generous side of memes, tidbits, and conspiracy theories — Bustle provided one of the more light-hearted lists to date — but the news that Leonardo DiCaprio finally won the big one is a nice bookend to a career that, in honesty, has had more ups than downs, something that is truly rare in Hollywood these days. For a career that has featured some of the biggest cinematic experiences in modern memory, the actor hasn’t allowed this to dampen or hinder him in his quest for continuing success. After all, many expected him to fizzle out after 1997’s Titanic — even DiCaprio was astounded by the popularity of that movie, one that ushered in Leo-Mania, an event recently remembered by the Washington Post.

Many expected Titanic to be the pinnacle of a career that, at the time, placed DiCaprio firmly in the minds of adoring teenage girls. His follow-up performances, in hindsight, seemed to want to break him out of this type-casting. The Man in the Iron Mask, a dark, menacing turn in The Beach, and Oscar-worthy Catch Me If You Can all seemed to elevate DiCaprio from behind his looks, proving that the actor can, in the case of the latter, act. In 2005, he received his first of four Best Actor nominations for The Aviator. The chase for an Oscar would start here and continue for many years until just last night, where he finally scooped the award for his riveting, tortured turn in The Revenant.

After his success, what does the future hold? Only he knows that, but in the meantime, DiCaprio can bask in the glory of his much-deserved, highly anticipated Oscar win. After all, it’s been on the cards for a while. His career has featured a host of Oscar snubs and close-calls, multiple nominations and accolades, and many outstanding, critically acclaimed performances.

With the celebrations well under way, and featuring minor spoilers, here are five stand-out moments from Leonardo DiCaprio’s illustrious career thus far, moments that, had the timing been slightly different, could have earned him an Oscar much sooner.

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Leonardo DiCaprio launched himself to stardom in the role of Arnie Grape. He would secure a Best Supporting Actor nomination for the role. [Image via Paramount Pictures]

What’s Eating Gilbert Grape? (1993)

With just a few movies under his young belt, DiCaprio impressed the world with his complex, vivid turn as Arnie Grape, a young boy with developmental disabilities. Starring alongside Johnny Depp, who played his titular older brother, DiCaprio would hold his own against the veteran thespian, wow the critics, and earn himself a Best Supporting Actor nomination in the process. Many thought he should have won for his portrayal, a convincing performance described, by some, as uncomfortable to watch. In an early interview, DiCaprio explained his research for such a difficult role.

“I had to really research and get into the mind of somebody with a disability like that. So I spent a few days at a home for mentally retarded teens. We just talked and I watched their mannerisms. People have these expectations that mentally retarded children are really crazy, but it’s not so. It’s refreshing to see them because everything’s so new to them.”

A pivotal early role, one that laid the foundations for Oscar glory. Twenty-three years later, he would finally win the big one, but this performance put everyone in Hollywood on notice.

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The Departed (2006)

Considering it was a remake of the immensely popular Hong Kong thriller Infernal Affairs (2002), The Departed was a critical and commercial success. A complex crime thriller, crafted and honed in Martin Scorsese’s trademark grit and subtle brutality, the film gave Leonardo DiCaprio a chance to shine amongst a stellar, A-list cast. Bouncing off an equally impressive Matt Damon in one of the better pairings of the ’00s and featuring Jack Nicholson, Mark Wahlberg (who received a Best Supporting Actor nomination for his efforts), and Martin Sheen, this gritty, urban tale of corruption provided the canvas for one of DiCaprio’s better turns in the last 10 years.

However, in the same year, he was nominated for in the Best Actor category for another film, Blood Diamond. Many thought he should have been nominated for his role of Billy Costigan too, or instead, his honest, conflicted, authentic portrayal of an undercover cop who infiltrates the Boston mob, a man behind overwhelming enemy lines, was one of the actor’s best to date. In an interview with About Entertainment, DiCaprio explained that the tough research, carried out with a former Boston resident, justified the intense performance.

“He told me about the tragedies of what was going on when he grew up and the gang violence and that sort of whole underworld, and that was not just to get acquainted with the accent. But it’s an entirely different place. I’d never spent any time in Boston and it was important for me to spend some time in Boston and hear the real stories and real accounts of what really went down, and meet some of the real characters.””

For a film that scooped multiple awards and nominations and made many “Best of 2006” lists, DiCaprio’s snub for his performance is probably one of the worst in the eyes of film critics. His collaborative relationship with Scorsese continues to this day, so hopefully there are more accolades to come in their partnership.

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Leonardo DiCaprio's turn as FBI director J. Edgar Hoover, was shunned by the Academy. It didn't receive any nominations, much to the surprise of critics. [Image via Warner Bros.]

J. Edgar (2011)

Despite mixed reviews on release, J. Edgar provided us with a powerhouse performance from Leonardo DiCaprio. Under Clint Eastwood’s light, efficient directing, the actor provided a subtle, persuasive performance of J. Edgar Hoover, the man who was tasked with cleaning up and professionalizing the FBI. A controversial figure in American culture, the task wasn’t an easy one, and although some particular details of his life were politely side-stepped, DiCaprio played the part to perfection. In an interview with the Telegraph, DiCaprio summed up his opinion of the former FBI director.

“I think he was a tragic figure and the only way he could receive love was through the workplace, which is why he was tyrannical about being in a position of power his entire life and why he manipulated everyone around him. His life was about protecting his own secrets and finding out other people’s.”

Of the five roles on this list, this one will draw some criticism. J. Edgar received mixed reviews, but putting aside potential plot issues and production values, DiCaprio’s performance scorches the celluloid; subtle and quiet, yes, but there’s a tortured soul burning beneath the surface, one that DiCaprio captures perfectly on film. It might not be the most remembered in his career, but it definitely prepared him for a couple of trickier, future roles.

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Leonardo DiCaprio teamed with Quentin Tarintino in 'Django Unchained,' much to the cinemagoers delight. [Image via The Weinstein Company]

Django Unchained (2012)

A year after J. Edgar, Leonardo DiCaprio would team up with one of this generation’s most influential directors: Quentin Tarantino. Set in Texas during 1858, the film depicts the story of Django (played by Jamie Foxx), a branded black slave who is promised freedom by Christoph Waltz’s bounty hunter if he assists him with locating three outlaws. Yet, despite the movie being based around Django, it’s DiCaprio who received the plaudits for his role.

As the racist, egotistical plantation owner Calvin Candie, it’s an immensely brave performance, one that had the potential to destroy an A-list career, so it’s a pity the Academy didn’t recognize it. Tossing racist slurs around like confetti — at the insistence of co-stars Samuel L. Jackson and Foxx — Candie is DiCaprio’s first ever role as an evil villain. If the evidence is this good, surely not his last. During a pivotal scene, the actor even cut his hand open due to a prop malfunction, but he continued the bloody scene to completion. That particular take made it into the final cut, and it’s a scene that’s webbed with tension, horror, and a stark, bold performance, one that’s only enhanced by the real blood on display.

On the controversial character, DiCaprio had his say.

“He’s the most deplorable human being I’ve ever read in a screenplay in my life. He was rotting from the inside. He was, you know, a young Louis the XIV that had been brought into a world of entitlement and lived his life … essentially owning other people.”

It may have been DiCaprio’s first role as a villain, but the performance was one of his best in recent years, one that, despite only holding restricted screen time, outshone every other performance in the movie. Despite being ignored by the Academy, he did receive several nominations from elsewhere, so it wasn’t a completely lost cause. Does it mean we’ll see DiCaprio play a villain more often? See below.

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Leonardo DiCaprio as Jordan Belfort in 'The Wolf of Wall Street.' This was expected to be DiCaprio's first Oscar win. [Image via Paramount Pictures]

The Wolf of Wall Street (2013)

Of all the films on this list, The Wolf of Wall Street was the film that many expected to hand Leonardo DiCaprio his first Oscar. The biographical black comedy was a critical success, nominated for five awards — including Best Actor for DiCaprio — and winning a slew of other accolades. Martin Scorsese’s fifth collaboration with DiCaprio featured another bold performance from the actor, one that wowed the critics despite the inclusion of explicit profanity, drug use, and sexual content.

Telling the tale of success-driven stockbroker Jordan Belfort, the film depicts how his New York City company engaged in rampant corruption and fraud on Wall Street, ultimately leading to his downfall. The film was controversial on release but secured DiCaprio’s status as a guaranteed draw, a Hollywood megastar. If you remember back to his early career — to performances in Romeo + Juliet, Titanic, or even Marvin’s Room — you could never envision the actor playing a role like this; it’s the complete Hollywood transformation.

On the criticism of the movie, reports that the film endorses Belfort’s corrupt lifestyle, DiCaprio was quick to step in. He spoke to Variety during an interview.

“There have been some reaction to why we don’t cut away to the victims and show the ramifications of their actions. And [Scorsese] said, ‘Look, I’m not here to make a didactic movie. I want to make a film that is reflective of who these people are.’ He has his own moral compass and feeling about who these people are, he doesn’t agree with the activity obviously, and it’s a cautionary tale.”

Despite his performance, DiCaprio didn’t win on this occasion. His nomination was the catalyst behind multiple memes and references on the internet, many claiming that DiCaprio could never win the big one. Three years later, and after last night’s events, we all know this is now a non-issue. He’s won the big one; and with his track record, it might not be that long until he wins another.

All of the above movies can be purchased on Blu-ray and DVD now.

[Image via Miramax Films]