Prolific A-lister Leonardo DiCaprio has famously been snubbed by the Academy Awards before finally securing a Best Actor Oscar for his work as Hugh Glass in The Revenant - but there were plenty of other DiCaprio roles, nominated or otherwise, that the actor deserved to win for. Known for taking on complex roles and historical biopics, DiCaprio has one of the most celebrated careers in the industry. After landing the recurring role of the troubled Luke Brower on the sitcom Growing Pains, DiCaprio soon shot to stardom for playing Arnie Grape in What's Eating Gilbert Grape?.

Becoming a frequent collaborator of famed director Martin Scorcese, DiCaprio starred in hit after critically acclaimed hit, portraying a variety of characters, each more complex than the last. He's proven that he has the talent to take on the hero, the villain, and everything in between over the course of his decades-long career, and isn't slowing down anytime soon. Utilizing his industry know-how, DiCaprio also became a successful producer, founding Appian Way Productions. While he's been honored by the Golden Globes, the BAFTAs, and countless other prestigious accolades, it seemed like the Academy Awards was purposefully ignoring his talents for years.

9 What's Eating Gilbert Grape (1993)

DiCaprio's big break was starring as Arnie Grape, the developmentally disabled brother of Johnny Depp's Gilbert Grape, in the coming-of-age drama What's Eating Gilbert Grape? He was even nominated for a Best ing Actor Award by the Oscars for his performance - a nomination he lost to Tommy Lee Jones for The Fugitive. Nevertheless, DiCaprio's performance stands the test of time as the role could've veered into offensive territory, but saw the actor succeeding. It's a testament to his talent that one of his very first parts was one of Leonardo DiCaprio's best films, as he plays Arnie with believability and fluidity while portraying staggering empathy using his eyes alone.

8 The Aviator (2004)

DiCaprio took on the role of real-life aviator and director Howard Hughes for the 2004 biopic The Aviator, a role that earned him a Best Actor Oscar nomination in 2005. Jamie Foxx instead picked up the award for Ray, and while it was an incredible biopic of its own, DiCaprio was snubbed once again. With The Aviator, DiCaprio proved that he had the chops to accurately and appropriately depict a character's tragic downward spiral as Hughes' struggles with OCD gradually begin to take over his life and career. DiCaprio's commitment to the role was nothing short of astounding as he tackles the complex individual with surprising grace and authenticity.

7 Blood Diamond (2006)

Leonardo DiCaprio's divisive Blood Diamond accent aside, the part of a mercenary and Rhodesian diamond smuggler broke new ground for DiCaprio and cemented his previously unseen abilities in the action genre. DiCaprio was nominated for a Best Actor Oscar for his performance as Danny Archer, an accolade he lost to Forest Whitaker for The Last King of Scotland. Blood Diamond showcased the versatility of DiCaprio's talents, tackling high-octane action sequences and quieter moments of surprising empathy from such a jaded character in equal measure. The battle that DiCaprio's character faces in Blood Diamond is both internal and external, and both are played out beautifully on the screen.

6 The Wolf Of Wall Street (2013)

One of DiCaprio's most famous contemporary roles was that of the real-life Wall Street broker Jordan Belfort in The Wolf of Wall Street. Outside of jump-starting Margot Robbie's career, The Wolf of Wall Street snagged DiCaprio yet another Best Actor Oscar nomination that he unfortunately lost. Matthew McConaughey won for Dallas Buyers Club that year and DiCaprio remained Oscar-less. Out of all the real-life figures that DiCaprio has portrayed, Belfort was by far the most controversial. DiCaprio deftly plays Belfort with a chilling hunger behind his eyes and continually grows more narcissistic and depraved as his wealth and drug abuse increase at an alarming rate.

5 Once Upon A Time In Hollywood (2019)

DiCaprio has starred in two Quentin Tarantino movies, but only Once Upon a Time in Hollywood earned him an Oscar nomination. That year, DiCaprio lost out on the Best Actor Oscar to Joaquin Phoenix for Joker. In Once Upon a Time in Hollywood, DiCaprio headlines as aging action star Rick Dalton, who is experiencing a transition in his career. While the movie is ultimately about the grisly Manson Family murders, Dalton is DiCaprio at his most engaging. He showcases a stunning magnetism in the role, struggling both internally and externally with the disappointment of his current career trajectory. DiCaprio artfully makes audiences feel both sorry for and infuriated with Rick.

4 Titanic (1997)

One of James Cameron's best movies, Titanic, did an Oscars sweep at the 1998 Academy Awards, and it seemed like everyone but DiCaprio was a winner. DiCaprio famously plays fictional third-class enger and artist Jack Dawson who falls in love with Kate Winslet's affluent and engaged Rose DeWitt Bukater while aboard the ill-fated RMS Titanic. Thanks in part to undeniable chemistry with Winslet, DiCaprio soars as Jack, bringing a much-needed levity to a tragic tale. He plays wide-eyed and hopeful astoundingly well, and the film saw DiCaprio as not just a rising star, but a '90s teen heartthrob.

3 The Departed (2006)

The Departed is well-known for its powerhouse performances, but there's no question that DiCaprio deserved an Oscar nod for his portrayal of the undercover rookie Billy Costigan. Though The Departed did win Best Picture at the 2007 Oscars, DiCaprio received not so much as a nomination for his engaging performance. In the role, DiCaprio skillfully portrays a man who is slowly questioning his morality as he delves deeper and deeper into the Irish mob. The subtle anxiety over his affair with Sullivan's girlfriend Madolyn and his increasing cognitive dissonance over having to commit acts that come into conflict with his beliefs is a battle that rages on the screen.

2 Django Unchained (2012)

Django Unchained was DiCaprio's first role in the highly-stylized world of Quentin Tarantino, and slave owner Calvin Candie proved to be his most depraved character yet. Chock full of Django Unchained should've earned DiCaprio a Best ing Actor nod at the very least. The role of Calvin Candie proved that DiCaprio could embody a despicable and heartless villain, capable of horrific violence and chilling shrewdness. DiCaprio steals every scene he appears in Django Unchained, oscillating between the aristocratic facade he displays for his white clients and the bestial rage he holds for his Black slaves with terrifying ease.

1 Romeo + Juliet (1996)

While DiCaprio has headlined two bombastic Baz Luhrmann flicks, Romeo + Juliet remains one of the actor's very best films - a film he should've won an Oscar for. A mark of true talent is when an actor can deliver their dialogue in flawless Shakespearian English and make it decipherable for contemporary audiences, and DiCaprio does that early in his career. Audiences swoon whenever DiCaprio's Romeo graces the screen, and he plays a well-worn character with refreshing ingenuity as he portrays different facets of the character that can't be surmised from one read-through of the text. He's dynamic, romantic, and a powerhouse as Romeo, cementing Leonardo DiCaprio's well-earned fame.