There is no proper way to evaluate the extraordinary career of Leonardo DiCaprio without offering a brief analysis of his major films and nominations. It should be acknowledged that DiCaprio has been nominated (including this year) for five Oscars, but his career is so much more than that. When evaluating his career, one soon realizes that DiCaprio easily could have been nominated another seven times, which truly makes the case as to how ridiculous it is that Leonardo DiCaprio has yet to win an Oscar. For 25 years Leonardo DiCaprio has captivated audiences with his versatile performances and is one of Hollywood’s most recognizable faces. Many have argued that Leonardo is arrogant and panders for an Oscar that he covets like Gollum coveting for the one ring in Lord of the Rings. While the metaphor hints at some truth, one cannot deny that Leonardo has completely thrown himself into every role he has played.
However, if one ever truly wants to laugh at how Leonardo DiCaprio got his start in the film business, please refer to his first film when he was 17…Critters 3.
On a more serious note, let us now look at Leonardo’s Oscar nominations for the purpose of ranking his “best” performances according to the Academy Awards. These rankings of his nominated performances are my personal opinion:
The Revenant (2015) – Truly Leonardo’s most transformative performance. Normally one of the faults of Leonardo’s acting is his inability to completely take himself out of his roles. Often it can feel that the audience is watching an extraordinary performance from him, but we never completely believe it is the character, but rather is “Leonardo playing THIS character.” That was not the scenario with The Revenant since the emotional core he offered the character was believable and the mere fact that the character barely speaks any lines throughout the film furthermore reinforced the need for Leonardo to truly become the character in order for it to have a level of authenticity. The Revenant is the best performance of his career so far.
What’s Eating Gilbert Grape (1993) – It is extraordinary to note that Leonardo essentially started his career with an Oscar nomination and it was deserved. What shocked most critics and moviegoers at the same time was the realization that Leonardo didn’t, in fact, have Down’s Syndrome, but was merely acting the role. The performance was so convincing and filled with heart that it stunned people. Also, considering Leonardo was 18 and this was one of his first performances, the Oscar wasn’t on his mind when acting in this role, which made his performance appear more natural and true-to-life. Any other year he would have won the Oscar for this performance, but he was in competition against Tommy Lee Jones (The Fugitive) and Ralph Fiennes (Schindler’s List) and there was no way he was about to beat either of those performances.
Wolf of Wall Street (2013) – Obviously the most showy performance of his career. It should be acknowledged that both the film and the performance is not for everyone. Wolf of Wall Street is crude and very much a in-your-face kind of film. While the film could have been deplorable for anyone watching it, it was because of Leonardo’s smug and arrogant performance that make both him and the film captivating to watch.
The Aviator (2004) – Most critics and pundits thought this would be the year and performance that would win Leonardo his first Oscar. He won his first Golden Globe for this role as the eccentric director turned aviator, Howard Hughes, and it was very much deserved. Leonardo perfectly captured the mystic of Howard Hughes, but he perfectly detailed in his performance how Hughes was a genius, but a victim to his own obsessive-compulsive neuroses.
Blood Diamond (2006) – This is the one outlier of Leonardo’s nominations, one that is difficult to comprehend as to why he was nominated. His performance was good, but average at best, especially when considering his performance in this film was nominated over his more stellar and extraordinary performance in The Departed (he did both films in 2006). Nonetheless, Leonardo’s role as a diamond smuggler who aids a fisherman in recuing his abducted son from the country’s cartels, is the best part of Blood Diamond.
Keep in mind, these are only the performances that the Academy decided to nominate. Let’s now look at many of Leonardo’s tremendous performances that easily could have gotten him another nomination. Like the nominated performances, I have ranked these performances from ‘most impressive’ to ‘impressive’ based upon my personal opinion.
The Departed (2006) – There is only one reason as to why Leonardo was not nominated for this film. Producers were reluctant to push this performance as Lead Actor and instead wanted to promote it as Supporting. Leonardo was against this and opted for his performance in Blood Diamond be pushed for a nomination instead in the Lead Actor category. This was an unfortunate mistake because there is no doubt Leonardo would have won for his role in The Departed. The level of paranoia and fear he instilled into his performance was one of the most memorable and realistic performances he ever gave.
Django Unchained (2012) – Learning his lesson from The Departed, Leonardo somewhat shocked moviegoers and critics when he took on a supporting role in Quentin Tarantino’s 2012 western. This was the first supporting role Leonardo took on in over twenty years, but even more shocking was the realization that Leonardo was slated to play the film’s villain: A vile, racist and vicious Plantation owner. Leonardo did not disappoint in the slightest. Not only was his performance unsettling to watch, but his very appearance caused moviegoers to recoil in disgust. It was, by far, one of the best performances of Leonardo’s career, one that everyone thought would finally win him an Oscar. However, something surprising happened that Oscars year: Leonardo was snubbed the nomination. Even more surprising was his co-star, Cristoph Waltz, ultimately won the Oscar. It was cruel irony for Leonardo.
Revolutionary Road (2008) – The 2008 film was the film that reunited Leonardo with Kate Winslet after their success together in 1997’s Titanic. Leonardo perfectly captured the role of the chauvinistic 1950s male, who initially gives his wife hopes of breaking free of the suburban life, only to shatter her dreams when he chooses his job over their happiness.
Catch Me If You Can (2002) – After Titanic, Leonardo’s career nearly tanked. Despite the success of Titanic, Leonardo was relegated to minimal performances that either embarrassed, such as The Man in the Iron Mask, or performances that diminished his talent, such as The Beach. Leonardo’s career was slowly vanishing and he needed a stellar comeback to remind people of his talent. That comeback was his performance in Steven Spielberg’s Catch Me If You Can. This was the comeback Leonardo needed and he was outstanding in his performance as true-life con artist Frank Abagnale Jr., who was able to successfully impersonate being a airline pilot, a doctor, and a legal prosecutor, all the while defrauding the United States of millions of dollars. Leonardo’s performance was charismatic and completely believable. Furthermore, he made the performance endearing, which allowed moviegoers to sympathize with him despite his illegal activities.
Inception (2010) – Inception was a unique and profound film from the creative mind of Christopher Nolan. At the center of the film was Leonardo’s performance as Cobb, a thief who steals corporate ideas from someone’s subconscious when they are asleep. Leonardo’s performance hinged on his character’s motivations, which was to be reunited with his children. The performance was showy and could have been devoid of substance, but Leonardo was sure to provide a complex character who is slowly losing his grip of reality and only wants to be back with his family again.
The Basketball Diaries (1995) – This was the film that truly catapulted Leonardo to fame after his initial success of What’s Eating Gilbert Grape, thus proving himself as a capable and versatile character. His performance as an aspiring basketball player who succumbs to heroin addiction and strives to do whatever he can, including prostituting himself, for another fix was a performance that stunned and shocked people. The film was controversial, which was partially why Leonardo likely did not see a nomination for his performance. Nonetheless, any Leonardo fan should absolutely see The Basketball Diaries if they want/need proof of Leonardo’s talent right when his career was starting.
Titanic (1997) – Titanic was the blockbuster hit that gave both Leonardo and Kate Winslet notoriety with film audiences. While Kate Winslet clearly overshadowed Leonardo’s performance, his acting as Jack Dawson was endearing and touching. His role hinged on coming off as an outsider to the higher society, but not coming off as uncouth. His performance needed to be devoid of pretention and instead be a performance that came from the heart. Without an impactful performance from Leonardo, the love story of Jack and Rose wouldn’t have had much clout and hopes for their survival from the Titanic sinking wouldn’t have achieved the level of emotion that the movie typically emotes from viewers.
As evidenced from this acting spotlight, the career of Leonardo DiCaprio has been vast and versatile. If anyone has proved to himself worthy of the Oscar, it is Leonardo with his ability to reinvent himself with every performance he acts within. It is also worth noting that if he were to win the Oscar for The Revenant, Leonardo is not going anywhere anytime soon. An Oscar win will likely empower him and inspire him to continue onwards as he has so far in his career. It is also likely that he will see himself with at least one more Oscar before his career concludes, whenever that may be.