A Career Exploration of the Wolf of Hollywood

Each month, The Circuit will do a deep-dive into the career of a different actor. From pantheon-level thespians, to actors with an IMDb page that will make you wonder “What were they thinking?” This month we look into the career of Oscar winner Leonardo DiCaprio.

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In 1991, Roseanne aired the “Home-Ec” episode that focused on Darlene at school. That episode featured many of her classmates, portrayed by actors and actresses that went uncredited. One of those uncredited classmates was none other than Leonardo DiCaprio. Bet they wish they had credited him in retrospect, huh?


From there, DiCaprio would ascend into the all-time ranks of acting. He could portray seemingly every type of character imaginable; teen heartthrob, classic literature figure, evil plantation-owning villain and leading man in a blockbuster. Coming up on nearly three decades of getting major roles in movies, DiCaprio has cemented his legacy as an actor who belongs in the pantheon of thespians.


Through all the films and all the incredible roles, only one Oscar sits on the DiCaprio fireplace. Looking back thirty years from now, people will wonder how Leo didn’t win more, and they will probably be right. And when that argument takes place in lounges all over the country, these are the seven films that will define the career of DiCaprio, and headline his resume for the Acting Mt. Rushmore.


1) What’s Eating Gilbert Grape? (1993)

At the raw age of 19 years old, Leonard DiCaprio filmed What’s Eating Gilbert Grape? alongside Johnny Depp, the lead of the film. This was just the fourth (4th!) film of his young career. He was in numerous television shows to start his acting career, but he had very little experience on the big screen until this film. Not only did he not fold under the pressure, he was nominated for an Oscar as Best Supporting Actor.


Playing Gilbert Grape’s younger brother Arnie Grape, who was mentally impaired, DiCaprio shined in this role. In a film about family growth, it was clear that DiCaprio had a wide range of talents. The emotional range in Arnie Grape was quite impressive, going from jovial to tortured like flipping a switch.


While there are many opportunities where you can point to and argue he should have won an Academy Award, this is one of the less egregious ones. His competition included Ralph Fiennes, John Malkovich, and the winner Tommy Lee Jones. Three actors that would make it difficult for anyone to emerge victorious, especially a raw teenager.


In many ways, his performance in What’s Eating Gilbert Grape? was a harbinger for the rest of DiCaprio’s career. The energetic and charming side of Arnie Grape would foreshadow his roles in The Wolf of Wall Street and Titanic. The tortured, emotional side foreshadowed his roles in Shutter Island and The Great Gatsby. This would prove to be just the beginning of an iconic career.


2) Titanic (1997)

Without a doubt, Titanic is one of the most divisive films ever made. Winning 10 (ten!) Oscars and ascending to the all-time box office king, many people loved the movie. However, between the 210 minute runtime (approaching Snyder Cut territory) and the age-old debate of whether or not there was room on that board for two, there are many people who don’t share the overwhelmingly positive sentiments. Feelings for the movie aside, there was one universal feeling coming out of the theater; DiCaprio is a force. And he’s here to stay.


Doubling-down on his role in Romeo and Juliet, Jack Dawson is yet another teen heartthrob who falls in love with someone he shouldn’t. From winning his way onto the ship in a game of poker (which undoubtedly induced gambling addictions all over the world), to drawing Rose like one of his French girls, to feeling on top of the world, to trusting Rose to never let go, DiCaprio stole the hearts of just about every teenage girl in the country. He was somehow able to exude playboy-esque charm and one-true-love romanticism all in one stowaway.


Despite 12 nominations and 10 wins at the 70th Oscars, Leo was not nominated. Travesty. Granted, he wouldn’t have beaten Nicholson for his role in As Good As It Gets, but he should have been nominated. A key note from the Best Actor category is that Matt Damon, a peer and rival of DiCaprio, was nominated for his role in Good Will Hunting, deservedly so. One has to wonder if this bothered DiCaprio, and maybe motivated him? (More on that later).


Titanic operated as the graduation from up-and-comer to supernova in the career of DiCaprio. While his early films featured strong roles and a boyish charm, the role of Jack Dawson announced to the world that DiCaprio can lead a film to both critical and box office success. After 10 Oscars and nearly $2.2 billion, Leo proved he could go from a 6th Man of the Year to an MVP.


3) The Departed (2006)

In 2006, the movie version of the Golden State Warriors came to life. Martin Scorsese directing on the sideline, Leonardo DiCaprio, Matt Damon and Jack Nicholson carrying the team, Mark Whalberg and Alec Baldwin coming off the bench and leading the second unit. The hype did not disappoint. Arguably the greatest Boston movie of all-time (an iconic Mt. Rushmore that includes Good Will Hunting and The Town), The Departed is an epic drama detailing the two diverging paths of a criminal masquerading as a cop and a cop masquerading as a criminal.


Leo shows off a fairly new side to his career, one where he is emotionally unstable and has to portray a bad guy, all while holding onto the reality that he is a good guy. DiCaprio brings his A game in this film, going toe-to-toe with all those acting legends. And winning. While the film focuses on the two cops, there is a clear winner between them. Not only is Leo’s character the one you are supposed to be rooting for because he’s the “good guy”, he’s the one you want to root for because of his performance. Leo acts circles around Damon in this film, which begs the question: Was Leo pissed off about the 1998 Oscars? It was clear that DiCaprio is the cast member who took this film the most seriously, as if he was out to prove something with all these legends surrounding him. Perhaps Damon getting a nomination over him led to Leo kicking his ass in this film.

Speaking of the Oscars, another oversight took place in 2007. The Departed grabbed five nominations and four wins at the 79th Oscars, but only one nomination was in the acting categories…. Mark Whalberg for Best Supporting Actor. WHAT!? Whalberg was great in the film. Every minute he was on screen, he stole the show. The problem was he was only in the film for about five minutes. His character is dialed up to 11 the entire time, he wins every scene he’s in, and his character arguably wins the movie, but with all the great acting performances in this film it seems baffling that his performance was the only one nominated.


This film is perhaps the biggest statement of Leo’s career. He proved he was a star in Titanic, but The Departed proved that he could go toe-to-toe with Oscar winning actors and kick their ass.


4) Django Unchained (2012)

In 2012 DiCaprio portrayed his most uncharacteristic character yet in Calvin Candie, a plantation owner. DiCaprio had almost always played the charming male lead that every woman fell in love with. So his turn as an evil, racist slave owner was quite a shock to the Hollywood system, but being the great thespian that he is, pulled it off in spades.


Between Inception in 2010 and Django in 2012, this was the beginning of one of the best five-year runs any actor has had. After those two films, Leo did The Great Gatsby, The Wolf of Wall Street, and The Revenant from 2010-2015. While each of his characters were uniquely different in this run, one thing stayed the same across all five films; DiCaprio was mesmerizing. Despite how deplorable his Candie character was, it was still great to see DiCaprio perform opposite Jamie Foxx and under the direction of Tarantino.


This is another film in Leo’s IMDb where only one actor got an Oscar nom, and it wasn’t him. Christopher Waltz won the Best Supporting Actor Oscar for this film, and looking back that doesn’t feel wrong. Could DiCaprio have been nominated? Yes. Could he have won? Sure. But unlike Titanic and The Departed, this doesn’t feel like an Academy crime.


This was a milestone performance in Leo’s career, as he broke away from the charming side and embraced the evil side and showed he could do more than just smile and look good (although with that 1850’s look, he does look good). Couple that with the social currency Django Unchained garnered, and this is a classic DiCaprio installment.


5) The Wolf of Wall Street (2013)

Speaking of piece-of-shit characters, enter Jordan Belfort. In the most electrifying entry in the filmography of Leonardo DiCaprio, he portrays stockbroker turned convicted felon Jordan Belfort in a jaw-dropping performance. From a jarring opening scene, to the iconic “I’m not going anyyyyywheeeeere” scene, this film has a breakneck pace that never lets up, and DiCaprio dazzles from start to finish.


DiCaprio pulls off a coked-out stockbroker trying to live the ultimate American-Dream life in a way that makes you want his character to die, yet also makes you want to be just like him (maybe without the coke). This film was the apex of the DiCaprio-Scorsese duo that churned out multiple gems like The Departed and The Aviator. Among all the accolades this film received, perhaps the best piece of marketing for The Wolf of Wall Street is that Leonardo DiCaprio gave the best performance of his career.


Which leads to the Oscars discussion revolving around this film. This was the 1992 Jordan season. The 2007 Brady season. The 2013 LeBron season. This was the capstone of his brilliant career, the film where thirty years from now when film students study the career of Leonardo DiCaprio, they’ll put in The Wolf of Wall Street. Yet… he didn’t win. Matthew McConaughey, who coincidentally is also in The Wolf of Wall Street (and delivers perhaps the best scene in the film, humming and telling Belfort that he needs to pump those rookie numbers up), took home Best Actor for his turn in Dallas Buyers Club. Now I love McConaughey, I think he’s great. Interstellar is one of my favorite movies of all-time, and he was phenomenal in Dallas Buyers Club. But this Oscar should have gone to DiCaprio, who at the time still had not won an Academy Award. This is a prime example of a win that doesn’t feel that wrong in the moment (although to me it did), but with each year that goes by it feels more and more wrong.

This was the drop-the-mic entry (literally, his character did that) in DiCaprio’s career, proving he can do anything on screen, and can do it better than anyone else can.


6) The Revenant (2015)

Ah, The Revenant. Or, as it should be called: The Revenant: The Make-Up Oscar. This film was undoubtedly the most physical performance of Leo’s career, as his Hugh Glass character traversed harsh wintery terrain to get back to civilization after fighting a bear (although it’s unlikely DiCaprio actually fought a bear on set). Based on a true story, The Revenant gave Leo an opportunity to show the Academy that he could take on the physically challenging role that often wins Oscars.


While this film has some notable actors like Tom Hardy and Will Poulter, and is based on a true story, the only thing most people remember from the film is the bear fight. And it was a good bear fight. But this is not the best performance of DiCaprio’s career, yet it netted him that elusive Best Actor Oscar win.


This was a make-up win. It felt like in 2016, and five years later it still feels like it. Like when a player is clearly fouled on one end and doesn’t get the call, so the ref calls a travel on the other end to make up for the blown call, the Academy realized they had let this go too far. DiCaprio deserved the win in 2014, and after two years of being a meme he finally got to be celebrated for his greatness. While it was his first win, it’s unlikely that it will be his last.


This film will be the “yeah, but” on DiCaprio’s Acting Mt. Rushmore resume. While it will likely be at the top of the list because of the Oscar, people will always say “yeah, but it wasn’t his best performance”. An unfortunate legacy for an otherwise solid film, The Revenant will always be the “yeah, but” film on the IMDb of Leonardo DiCaprio.


7) Once Upon a Time… In Hollywood

And finally there is Leo’s latest installment in his “Greatest Hits” track, Once Upon a Time… In Hollywood. The film followed DiCaprio’s Rick Dalton and Brad Pitt’s Cliff Booth as they struggled to find work in Hollywood as they approached the twilight of their careers. In a film that was visually striking and thematically captivating, the two actors stole the show.

While DiCaprio was excellent in Hollywood, earning himself yet another nomination for Best Actor, Brad Pitt was the big winner, taking home the win for Best Supporting Actor. When we look back at this movie, we will likely think of Pitt first. But, the discussion of Pitt will ultimately lead to the underrated performance of DiCaprio. From him spiraling out of control in his trailer, to the revolving door of the roles his character played, DiCaprio nailed one of the toughest jobs in acting; playing an actor. Joining the likes of Joey Tribiani and Michael in Birdman, Leonardo DiCaprio takes his turn as portraying an actor who is entering the final chapters of his career and is struggling to find work (I’ll bet car that Leo never struggles to find work).


With 10 nominations and 2 wins, Once Upon a Time... in Hollywood was one of the premiere films at the 92nd Oscars. While there certainly was an argument for Leo to net his second Oscar, losing to Joaquin Phoenix for his role in Joker is defensible. While DiCaprio was great, Phoenix turned in a hauntingly beautiful performance in a role that required a physical transformation, something the Academy recognizes again and again.


This is the mind-over-body film for DiCaprio in his career. While he did quite a little bit of physical activity in this role, it didn’t equal the likes of The Revenant or The Departed. This film showed that Leo can flex his mind and out-act anyone with how smart he is and how much he knows about acting. Like LeBron on the Lakers, Leo is beginning to transition into the point in his career where he isn’t trying to catch Tom Hanks if he can, but he is showing how cerebral he is. And how great he is.


In Conclusion

While his career is far from over, and there are undoubtedly 5-7 more performances in his career that will be in this conversation, we can start to look at the Mt. Rushmore of Leonardo DiCaprio’s career. Looking over his entire filmography, there are four films that will reside on his mountainside; The Wolf of Wall Street, The Revenant, Titanic, & Once Upon a Time… in Hollywood. This list is subject to change, and the debates will rage on until the end of time, but those are the four films that, to this point, have defined the career of the legendary Leonardo DiCaprio.


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