10 best Leonardo DiCaprio movies

Leonardo DiCaprio in Titanic, one of his best movies and among his finest performances
Leonardo DiCaprio in Titanic, one of his best movies and among his finest performances

Leonardo DiCaprio finally won the Best Actor Oscar earlier this year for his electrifying portrayal of a man seeking justice for his murdered son in The Revenant, but over the years Leo has given movie fans many memorable performances.

He often plays unwavering idealists who meet a tragic end or men shouldering the heavy burden of expectation and responsibility alone.

A private man, Leo won the adoration of audiences with his natural, understated talent. This led ordinary people the world over to back him for Oscar victory and celebrate his success as if it were their own.

Here in no particular order are 10 of his best performances and some of his best movies:

10 This Boy’s Life – Toby

Based on the memoir by Tobias Wolff, This Boy’s Life (Caton-Jones, 1993, USA) tells the story of teenaged Toby’s struggle to retain a sense of self and achieve his potential in the face of abuse from his oppressive new step-father.

DiCaprio impressed critics by holding his own opposite Robert De Niro, who was at the top of his game. De Niro gave a chilling performance as charmer Dwight who romances Toby’s mother but intimidates Toby and his own children when she is away.

However, it was Leo who had the ability to make us feel every blow and every unkind word Toby suffered.

9 Titanic – Jack Dawson

Titanic (Cameron, 1997, USA) captured the hearts and imaginations of audiences, moving them to tears and prompting them to return to theatres multiple times for repeat viewings.

Nowadays people remember the film for its controversial ending (could Jack have survived?) and the kitsch Celine Dion soundtrack.

It is important to also remember that the spirit of the movie came from Leo and Kate Winslet’s strong central performances which steered the film on a course for box office success.

The pair gave Jack and Rose a youthful exuberance that brought what seemed like ancient history back to life for modern audiences.

8 Revolutionary Road – Frank Wheeler

Revolutionary Road (Mendes, 2008, UK/USA) is about a married couple, Frank and April Wheeler, and their struggle to reconcile the life they wanted for themselves with the prison society has built for them.

Young Frank is well travelled and has different ideas about how married life could be but, as he gets older and has kids, his sense of familial responsibility weighs him down.

Leo skilfully portrays Frank’s transition from a young optimist into a cog in the corporate machine.

We see Frank get sucked into the rat race, with his belief in its importance growing even as it slowly destroys him and his family.

7 Romeo + Juliet – Romeo Montague

Leo was dismissed by critics as a commercial teen-heartthrob, but what he brought to Romeo + Juliet (Luhrmann, 1996, USA) was much more than superficial.

Leo plays Romeo as if he were a jaded L.A. teen, the melancholia is palpable, but he is awakened when he meets Juliet.

The movie updates Shakespeare for the modern age, but in particular it is Leo’s magical ability to convey feeling and emotion that translates the 1590’s to the vibrant 1990’s.

DiCaprio fits perfectly with Baz Luhrmann’s filmmaking style as both seem drawn to tragedies where love and beauty are unable to triumph but might yet influence others in the long run.

6 What’s Eating Gilbert Grape – Arnie Grape

Gilbert, played by Johnny Depp, struggles to bear responsibility for his siblings as his house-bound mother is unable to hold down a job.

Leo plays Arnie Grape, Gilbert’s little brother, who suffers from a mental impairment.

Depp was hot property at the time, but DiCaprio really stole the show, depicting Arnie as full of love for life in spite of his disability.

What’s Eating Gilbert Grape (Hallström, 1993, USA) drew the Academy’s attention to DiCaprio for the first time, earning him a Best Supporting Actor nomination.

The film as a whole seems to orbit around Leo despite other strong performances from the ensemble cast.

5 The Great Gatsby – Jay Gatsby

DiCaprio’s decision to take on the role of Gatsby in The Great Gatsby (Luhrmann, 2013, AU/USA) was an interesting one because of how it parallels his own life.

Eligible millionaire Jay Gatsby is misunderstood by those around him, a mystery to be solved. Of course, the secret Gatsby is hiding behind his wealth is the fact that he is just a genuine, ordinary guy, a fragile romantic.

Leo plays Gatsby as a lonely, tragic figure. We see heartache behind his eyes as he tries to win Daisy’s love.

He exudes cool confidence around everyone, but around her, he becomes socially awkward, love-sick and vulnerable.

4 The Wolf of Wall Street – Jordan Belfort

Leo doesn’t tend to play villains and he isn’t particularly known as a comedic actor but as Jordan Belfort in biopic The Wolf of Wall Street (Scorsese, 2013, USA) he is absolutely hilarious as the morally flawed city banker.

Belfort is so excited about his drug, sex and crime-fuelled lifestyle that it takes a near-death experience for him to change his ways.

Leo and co-star Jonah Hill make a great duo, playing off of one another, both bringing a likability to the characters that it would be hard to find in other actors or indeed in the real life bankers.

3 Catch Me If You Can – Frank Abagnale Jr.

In Catch Me If You Can (Spielberg, 2002, USA/CA) Leo plays one man with many roles.

Young Fank Abagnale Jr. discovers that it is easier to play a part than to be the protagonist of his own life, so he runs away from home to become a fraudster. Tom Hanks, as FBI agent Carl Hanratty, tracks Frank for years trying to catch him.

The interplay between the two actors is superb. Carl becomes a surrogate father figure, the only person who sees through Frank’s disguises.

The story rests on DiCaprio’s ability to simultaneously convey Frank’s thrill at being perceived as a ‘somebody’ and his fear of being found out.

2 The Departed – Billy

The Departed (Scorsese, 2006, USA/HK) is the tale of two kids growing up in crime-ridden Boston.

Billy (DiCaprio) trains as a police officer but must go undercover, returning to the life he tried to escape, to inform on mob boss Costello. Colin (Matt Damon) idolises Costello and trains as a cop to infiltrate the special investigation unit, working against the police from the inside.

Leo plays another multi-layered character with a double life; a good guy who has to put up a hard front. Billy wants more but the system keeps on dragging him down.

Another tragic figure, framed by society’s lens, Leo nails it.

1 Shutter Island – Teddy Daniels

Shutter Island (Scorsese, 2010, USA) starts with Detective Teddy Daniels and his partner Chuck arriving on the island to investigate the disappearance of a mental patient.

Teddy is haunted by family tragedy and his experiences in the War. Near the end it is revealed that (SPOILER ALERT) Teddy is himself a patient on the island, participating in a new role-play therapy.

Shutter Island is a movie you need to view twice to truly appreciate what Leo does with his character.

Leo switches adeptly between sick Teddy, genuinely believing in his protective fantasy, and ‘well’ Teddy a guilt ridden-man, indulging in farce to avoid facing himself. A triumph!

Do you have a favorite Leonardo DiCaprio movie  or performance? Let us know in the comments!

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