6 Leonardo DiCaprio performances I still can’t believe didn’t win an Oscar

It was clear from an early age that Leonardo DiCaprio possessed something special. He appeared on television at just five years old, with his first roles in shows like Romper Room and Growing Pains. Shortly after making his big-screen debut in 1991 with the sci-fi horror Critters 3, he was nominated for Best Supporting Actor for What’s Eating Gilbert Grape (1993), playing the mentally challenged brother of Johnny Depp’s character. Even then, it was possible to foresee what we’re witnessing today – a career defined by one hit after another and a level of fame few ever reach.

But instead of choosing the typical leading-man roles, Leonardo opted for challenging ones. Films like The Basketball Diaries and This Boy’s Life were hardly the kind of projects that guaranteed commercial success, which made his decision to star in James Cameron’s epic romance about the sinking of the Titanic all the more significant – and ironically, the one that catapulted him to true movie-star status. The film went on to win a record eleven Oscars, though none for acting. DiCaprio’s craft flourished even further in the early 2000s with Gangs of New York and Catch Me If You Can, shot back-to-back with two of cinema’s greatest directors. His collaboration with Martin Scorsese would soon become one of the most fruitful actor-director partnerships in film history, yielding some of the finest performances of his career.

Despite multiple nominations, the golden statuette eluded him for so long that it became the subject of countless viral jokes – with some even joking that one day, when a biopic about him is made, the actor playing DiCaprio will win the Oscar instead. In 2015, he finally took home the prestigious award for The Revenant. On the occasion of his 51st birthday, here are some of Leonardo’s performances that, without question, deserved Academy recognition.

The Wolf of Wall Street

Running for over three hours and rated restricted, The Wolf of Wall Street keeps viewers captivated from start to finish without a single dull moment. DiCaprio’s portrayal of Wall Street con artist Jordan Belfort in this modern Scorsese classic is hypnotic, hilarious, and deeply unsettling all at once. That year, at the 86th Academy Awards, Leonardo faced tough competition from Chiwetel Ejiofor (12 Years a Slave), Christian Bale (American Hustle), Bruce Dern (Nebraska), and ultimately the winner, Matthew McConaughey (Dallas Buyers Club).

Photo: Paramount Pictures

Catch Me If You Can

It’s well known that the filming of Steven Spielberg’s lighthearted con-artist comedy was delayed due to Martin Scorsese’s lengthy Gangs of New York production, but the most fascinating fact is how quickly Leonardo DiCaprio managed to transform himself. Here he convincingly plays Frank Abagnale as a high-school student, following his story over just a few years while maintaining a sense of youthful innocence beneath the surface. Acting alongside Tom Hanks and Christopher Walken, DiCaprio’s brilliant performance proved he could easily hold his own against Hollywood’s biggest names—in both talent and presence. He wasn’t nominated for an Oscar that year, when Adrien Brody rightly took home the golden statue for the unforgettable The Pianist.

The Departed

The year Leonardo was nominated for the wrong film. Although Scorsese has said that The Departed was made as a commercial film and that he never imagined it would earn him his first Oscar for Best Director, DiCaprio’s portrayal of an undercover NYPD agent was deceptively simple and, in truth, underrated. Acting alongside Jack Nicholson and Matt Damon, he had to balance between two practically different identities while maintaining the emotional core of his character amid the chaos. He executed it flawlessly, playing a man on the edge of sanity right up to the film’s shocking conclusion. Yet that year, he was nominated for Blood Diamond, in which he played diamond smuggler Danny Archer, not for The Departed.

Photo: Warner Bros. Entertainment Inc.

The Aviator

Although DiCaprio is excellent in Gangs of New York, his second collaboration with Scorsese is a true masterpiece. He fully inhabits the role of eccentric filmmaker and aviation pioneer Howard Hughes, bringing just enough empathy for the audience to truly understand him. It was a tremendous challenge—not only in execution but also in portraying such a vast portion of Hughes’s life, something that could easily intimidate many actors. For this role, DiCaprio won the Golden Globe and received another Academy Award nomination, though the Oscar ultimately went to Jamie Foxx for Ray.

Django Unchained

DiCaprio and Quentin Tarantino had been planning to work together for years, and although it almost happened on Inglourious Basterds, Tarantino had an even more repulsive character in mind for him. This is, in fact, the only character Tarantino has admitted to truly hating, and Leonardo brings Calvin Candie—the cruel plantation owner—to life with a mix of delight, aggression, and Southern charm. It’s arguably his most terrifying role, as he shifts seamlessly from playful to barbaric, capturing the moment you realize a man can be both irresistibly charming and horrifyingly evil at the same time—and you can’t look away. Fascinatingly, and somewhat frustratingly, DiCaprio wasn’t nominated for an Oscar for this performance.

Photo: The Weinstein Company

Inception

A stunningly complex and intricate science-fiction thriller by Christopher Nolan features Leonardo DiCaprio as a professional thief tasked with implanting an idea into someone’s mind—a process known in the film as inception. To succeed, his character must confront his own demons, haunted by a nostalgic and painful guilt over the death of his wife, Mal. Although the film was a massive success with both critics and audiences, its imaginative and elaborate plot may have overshadowed DiCaprio’s clever and deeply thoughtful performance. That same year, he delivered another remarkable turn in Shutter Island, whose chilling final soundtrack still echoes in my mind as the first thing I associate with the film. In the end, however, the Academy favored Jeff Bridges’ portrayal of a washed-up country musician in Crazy Heart.