In Five Films: Leonardo DiCaprio

Can an entire career be captured in just five films? With In Five Films, we attempt to showcase every side of a particular filmmaker, actor, or film person in just a handful of picks.

Few stars have carved out a career and a reputation for quality like Leonardo DiCaprio. A child actor who got his start with a part in much maligned horror sequel Tremors 3, he quickly became renowned for his sensitive and often complicated depictions of adolescence in films like What's Eating Gilbert Grape? and The Basketball Diaries. Then, cast as the co-lead in James Cameron's historical epic Titanic, he was launched to global fame and made an instant heartthrob.

With DiCaprio, it's all about the charisma, the boyish charm, the good looks. But struggling to carve a path in the immediate years after Titanic, he later found his groove again with a series of roles demanding a degree of intensity – chosen, perhaps, in a conscious effort to show that his success wasn't defined entirely by his handsomeness. In more recent years, he's relaxed into stranger and more comically-minded roles, unafraid to chew the scenery and even play villain. As such, he feels like one of the most malleable stars at work today, able to slip into a variety of manners and accents – but never without the sense of craft that always comes attached to a DiCaprio performance.

He has, of course, worked with Hollywood's finest filmmakers, from Spielberg to Scorsese ,where success and box office numbers are guaranteed, though they have used him equally to their advantage, relying on both his star power and a willingness to spin our perception. And somehow DiCaprio has retained his spot as the biggest star on the planet for over two decades – a testament to just how picky he is when it comes to choosing his next big projects. Put it down to the fact that he rarely makes more than one picture every few years; and so whenever he returns to our screens, it feels like an event – something to celebrate.

To coincide with the 10th anniversary re-release of Inception, we look back at DiCaprio's singular appeal in just five films. With so many great and iconic performances, it certainly wasn't easy.

Titanic (1997)

Where to watch it: Various streaming services

It is one of the most famous performances in one of the most famous movies ever made – for a time the biggest movie ever. Here DiCaprio, endlessly confident, with a charm and lust for life that is so infectious, plays the poor American Jack Dawson who boards the ill-fated ship of dreams and falls in love with Kate Winslet's rich Rose DeWitt Bukater. I estimate that DiCaprio's performance contributed to almost half of this film's box office success – the John Williams score to Spielberg's Jaws. Of course, it made him into the biggest star in the world, achieving the kind of fan mania that only The Beatles had generated up to that point. Some might say that this is a more shallow performance than we're used to now from an actor of his calibre; but to deny the sheer star power that had people going back to theatres repeatedly would be to deny what fundamentally makes DiCaprio so luminous.

Catch Me if You Can (2002)

Where to watch it: Various streaming services

Here is DiCaprio riffing on the easygoing charm and wink-wink boyishness that made his career, playing the real life con man Frank Abagnale, who travelled the United States posing as a doctor, a lawyer, a teacher, a pilot. Of course, for Spielberg's film to work, we must believe that so many would be duped by this act, and DiCaprio is flawlessly cast in the role. There's a sense here of DiCaprio using Catch Me if You Can as a kind of transitory film – a kind of middle ground between two stages of his career. Whereas other attempts to be “edgy,” post-Titanic, were less successful in ushering in a new era for DiCaprio (The Beach springs to mind), this is a wildly entertaining and layered performance, lively and spirited, but flavoured with just the right amount of melancholy and self-destructiveness.

The Wolf of Wall Street (2013)

Where to watch it: Various streaming services

Pound for pound, this might just be DiCaprio's greatest turn; a brilliant intersection of his more serious acting performances yet displaying an exuberant talent for comedy, especially in his interactions with Jonah Hill. As the real life Wall Street banker Jordan Belfort, he relishes every moment on screen, at times even bordering on the cartoonish. There is a pure wild streak in every line delivery, coupled with a boyish energy that – despite his character's outrageous behaviour – keeps you rooting for him. Is it too much to say this is the performance he was born to play? It feels like a showcase for everything that has made DiCaprio such a star, spread across three dizzying hours. Matthew McConaughey beat him to the post for the Best Actor Academy Award this year, but there's an argument to be made that DiCaprio deserved the Oscar equally.

The Revenant (2015)

Where to watch it: Various streaming services

This is an intense and gruelling turn from DiCaprio to match an intense and gruelling picture. He plays fur trapper Hugh Glass, who is mauled by a bear and left by his accomplices to die in the deepest, coldest wilderness. DiCaprio taps into something deep and primal here; a thousand yard stare and a mouthful of spittle. His performance is almost entirely physical and eventually animalistic, but he brilliantly captures a broken man whose desire for revenge allows him to go to extraordinary lengths in the face of insurmountable odds. The shoot, a reportedly punishing experience, perhaps allowed him to channel his frustrations into that relentless icy gaze. Though it is strange that DiCaprio's least vocal performance is the one that bagged him is first Academy Award. Or just mere proof that an actor putting themselves through hell is still the best way to the Academy's heart.

Once Upon a Time in Hollywood (2019)

Where to watch it: Various streaming services 

Quentin Tarantino's melancholy ode to the end of the '60s offer a far more laid back experience than one might expect from the director of Kill Bill and Reservoir Dogs. DiCaprio, who already worked wonders as a sadist Southern plantation owner in the spaghetti western Django Unchained, is also perfectly cast in his second Tarantino effort as Rick Dalton, a B-movie film star whose career is falling apart at the seams. What DiCaprio manages is to make an egotistic and at times pathetic character into somebody we genuinely root for. Dalton's bromance with his best friend and stuntman, Cliff Booth, played by Brad Pitt, also allows the actor some of the most intimate work of his career. His Django Unchained performance is exemplary, but I think this one has more shades and complexity, and is more revealing of DiCaprio the man.