Leonardo DiCaprio is one of the highest-grossing actors of all time and has established himself as one of the most talented actors of his generation, with over sixty projects to his name. As a four-time Academy Award nominee and one-time winner, Leonardo has achieved critical acclaim for his variety of roles in films ranging from romantic comedies to comic book adaptations. Since his debut in the 1993 film ‘What’s Eating Gilbert Grape’, DiCaprio has become known for his intense and methodical performances in films adapted from real-life stories and events.

In this article, we take a look at Leo’s leading roles, and rank his best movies from the early days of his career up to today. We’ll discuss why each title deserves its place on the list, examining each performance and the cultural legacy of the films.

The Departed (2006)

William Monahan’s The Departed was not only an Oscars favourite, but also an iconic collaboration between one of the best ensemble casts in cinematic history. The movie follows a parallel storyline involving the Boston police and organised crime families, with Leonardo DiCaprio, Matt Damon and Jack Nicholson leading the casts as each story intertwines.

DiCaprio takes the leading role of Billy Costigan, Jr., a police officer who goes undercover to investigate crime syndicates. He plays the role with his usual intensity while dealing with the murky moral issues that threaten to compromise his cover. His performance surprisingly won him an Oscar nomination, making it one of his highest-praised roles.

The Revenant (2015)

The Revenant partners DiCaprio with Alejandro González Iñárritu to craft a drama about overcoming insurmountable obstacles after a hunting expedition goes wrong. The film follows explorer Hugh Glass’s journey of survival and revenge, with DiCaprio at the helm.

Interestingly, the actor undertook a gruelling shoot that went on for over nine months, often requiring extreme methods to capture some of the film’s most demanding scenes. In addition, he survived the harsh conditions of the Canadian Rocky Mountains for weeks without food and water during filming. His enthusiasm and rigour pushed him over the finish line and contributed to a final product that resonated well with audiences, earning him an Oscar for lead actor and a Golden Globe award.

Shutter Island (2010)

Released by Martin Scorsese in 2010, Shutter Island is considered a modern classic. The psychological thriller features DiCaprio as the US Marshall Edward Daniels, who investigates a hospital for the criminally insane, only to uncover a complicated web of secrets and lies.

Leo puts in a gripping performance as the understandably tortured and confused Daniels, expertly balancing a timeline that makes it difficult for audiences to tell exactly where reality ends and illusion begins. His suspenseful and remarkably realistic performance earned him a Golden Globe nomination and cemented Shutter Island as an essential watch for any fan of the genre.

Inception (2010)

Playing opposite Ellen Page and Joseph Gordon-Levitt, Inception stars DiCaprio as Dom Cobb, an advisor and thief-for-hire of corporate secrets. Cobb and his team navigate their way through the subconscious while they face time and memory manipulation.

The Christopher Nolan-directed movie stands out as the subject of numerous philosophical and scientific debates, winning four Academy Awards including one for best visual effects. In addition, the film was a global box-office success and contributed to DiCaprio’s elevation to leading man status. His performance is both thrilling and subtle, and demonstrate why he’s emerged as one of the most sought-after actors.

Django Unchained (2012)

Quentin Tarantino’s Django Unchained sees DiCaprio take on the role of the antagonist, plantation owner Calvin Candie. The movie stars Jamie Foxx as Django, a freed slave who teams up with bounty hunter Dr. King Schultz (Christoph Waltz) to rescue his wife from enslavement.

DiCaprio’s performance as the cruel and relentless Candie effectively conveys the sadistic nature of his character and captivates audiences as they witness him constantly shifting between charm and danger. His edginess further drives home the grim realities of slavery in the 17th century, giving us a stark reminder of the human suffering that still effects us today.

The Wolf of Wall Street (2013)

The Wolf of Wall Street brought DiCaprio and Scorsese back together and adds another noteworthy notch on their belt. The movie follows the life of stockbroker and entrepreneur Jordan Belfort (DiCaprio), covering his wild lifestyles and success in Wall Street.

DiCaprio’s electric performance won him a Golden Globe, and is considered one of his finest roles up to date. The film also highlights the act of corruption and moral bankruptcy stemming from greed and power. It went on to become an awards favourite, and is considered one of the most iconic films of the era.

The Great Gatsby (2013)

Starring alongside Tobey Maguire, The Great Gatsby tells the classic story of the wealthy Jay Gatsby and the object of his affections, the wealthy Daisy Buchanan. DiCaprio takes on the leading role of the movie’s titular character and brings the enigmatic tycoon to life.

The film further proves DiCaprio’s acting range, capacity to captivate an audience and most of all, his attention to detail as Gatsby. He demonstrates his versatility once again with his abilities to convey emotions without words and get lost in the role of a troubled soul yearning for true love. With DiCaprio’s performance, The Great Gatsby stands out as one of the classic adaptions and inevitably gained a cult classic status.

Once Upon a Time in Hollywood (2019)

Praised by both fans and critics alike, Once Upon a Time in Hollywood features DiCaprio as fading TV star Rick Dalton and Brad Pitt as his close friend and stuntman Cliff Booth.

The film takes a look at the end of Hollywood’s golden age and the emergence of a new Hollywood, with DiCaprio and Pitt as the last men standing. Despite its slower pace, the humour inherent in the dialogue and the performances of the leading men are sure to captivate viewers.

DiCaprio’s character takes centre stage, with viewers following him as he navigates the pain of obsolescence and attempts to cling to his fading fame. For DiCaprio, his role as Dalton has earned him his sixth Oscar nomination, making it one of his strongest roles to date.

Blood Diamond (2006)

Another of DiCaprio’s signature performances, Blood Diamond follows the fight of injustice and triumphs of human spirit. The movie starred Djimon Hounsou as Solomon Vandy and DiCaprio as Danny Archer, a South African smuggler.

The film forces to the surface the issues surrounding conflict diamonds, and confronts the audience with the realities of warring Africa. DiCaprio brings Archer to life, highlighting the character’s suffering and moral conflicts in a masterful performance. His powerful portrayal earned him an Academy Award nomination and recognises his ability to take on an emotionally torn role.

From his revolutionary roles in The Revenant and The Great Gatsby, to his memorable parts in The Departed and Blood Diamond; Leonardo DiCaprio has earned a place in cinematic history. His genuine passion for his craft has enabled him to bring life to every character he’s portrayed, highlighting his versatility as an actor.

This article has explored Leo’s leading roles and ranked his best movies, exploring why each film deserves its place on the list and discussing the actor’s performances in detail.

There is no doubt that the Academy Award-winning thespian will continue to captivate audiences in the years to come, with an unfathomable range of performance that make him one of the greatest of our time.