Simply hear the name Leonardo DiCaprio and you know you’re in for thrilling and absorbing viewing. A-lister nonpareil, the actor stars in some of the best films of the 21st century, from The Beach to Gangs of New York, Shutter Island to Django Unchained. He has shapeshifted and evolved before our eyes from a pretty-faced 1990s heartthrob to a versatile leading man who can play drama and comedy with equal skill. At this point, he’s practically his own genre – regardless of whether in a gangster film or a historical biopic. One can simply be “in the mood for Leo”.
DiCaprio has long had a propensity for working with the best English language filmmakers in existence, and his latest is no different. His first release in two years – in cinemas on 26 September – is action thriller One Battle After Another, which sees DiCaprio work with Paul Thomas Anderson (beloved auteur director of Boogie Nights and There will be Blood) for the first time. This is what you might call A Big Deal.
Anderson is known for pushing already-great actors into their most unpredictable and poignant performances – take Adam Sandler in Punch-Drunk Love or Tom Cruise in Magnolia – so it’s thrilling to think of what the director can do with one of the most garlanded (awards aside) leading men in the world.
In anticipation for what may be another lauded role, here’s a round-up of DiCaprio’s eight very best performances. (Spoiler: the one he actually finally got an Oscar for doesn’t even make the cut.)
8. Titanic (1997)
Directed by James Cameron
Even beyond Titanic’s classic cinema moments that have been quoted into oblivion – from “I’m the king of the world” and “Don’t let go, Jack”, to the steamed-up car windows of that sex scene – it remains one of the most entertaining, spectacle-driven films ever put to screen. DiCaprio is effortlessly charming and instantly likeable as the cheeky, roguish Jack, who teaches young Rose (Kate Winslet) how to spit over the deck and dance an Irish jig. That there’s genuine chemistry with Winslet is clear, and DiCaprio’s performance is so real, it’s impossible not to get swept up in the emotion.
7. Romeo & Juliet (1996)
Directed by Baz Luhrmann
DiCaprio had been a child actor in an array of indie films prior to breaking out in Titanic, and here, in the year prior, makes an adorable, impetuous young Romeo in Baz Luhrmann’s deliriously maximalist reimagining of Shakespeare’s most famous work. It’s difficult to imagine a more transcendently romantic moment than the one where DiCaprio, wet and floppy-haired in a knight’s fancy dress costume, looks through an extravagant blue fish tank and locks eyes for the first time with a shy Claire Danes, who is dressed as an angel. He captures Shakespeare’s iambic pentameter with surprising fluidity and a youthful spirit – and, along with it, the imaginations of a whole new generation.
6. Catch Me If You Can (2002)
Directed by Steven Spielberg
A still fresh-faced young DiCaprio charms and cons his way through Spielberg’s retro caper, which follows the life of the real Frank Abagnale Jr, who lived under an impressive set of false identities with little but charisma to guide him (and the FBI to chase him). DiCaprio handles the film’s comedic and playful moments with ease, whether he’s bluffing his way into a pilot’s uniform or dodging Tom Hanks. There’s a real streak of boyish vulnerability behind his wolfish smile, too, making for a sympathetic protagonist in spite of his tangled web of near-pathological conman lies.
Catch Me If You Can was a box office smash hit, and its lasting critical and cultural impact is down largely to DiCaprio. It cemented his transition into more mature, complex roles – and showed he was more than just a curtain-haired teen pin-up.
5. Killers of the Flower Moon (2023)
Directed by Martin Scorsese
In one of DiCaprio’s least likeable roles, he plays real-life criminal Ernest Burkhart – a near-illiterate WWI veteran who gloms onto a wealthy Native American wife when his powerful uncle encourages him to find a way to take advantage. Ignorant, racist, and idle, he is soon brought in on a murderous conspiracy, aiding and abetting the strategic bumping-off of his wife’s various family members, thus clearing the way to become a very rich man. Bone-stupid and lantern-jawed, DiCaprio plays ignorance in a way which is both comic and frightening; it’s courageous of him to play someone so deeply detestable.
4. The Departed (2006)
Directed by Martin Scorsese
Much has been made of the long collaboration between master director Martin Scorsese and DiCaprio, a cinematic pairing that accounts for many of the entries on this list, but never fails to amaze in its scope. Here, in cop-and-crime flick The Departed, DiCaprio is the closest we come to a moral centre, dragged into the undertow as an undercover police officer in the Boston underworld long run by legendary mobster Frank Costello (a terrifying Jack Nicholson).
There’s something genuinely heartwrenching about the slow entrapment of DiCaprio’s well-intentioned protagonist here, particularly in his scenes opposite his psychiatrist, played by Vera Farmiga. As the increasingly sleepless, paranoid pawn in a larger game, DiCaprio’s desperation and fear are palpable.
3. The Aviator (2004)
Directed by Martin Scorsese
DiCaprio was nominated for his second Academy Award for Best Actor for this personification of a legendary American figure. Scorsese took on his beloved Golden Age Hollywood with this sprawling, expensively mounted epic exploring the life and times of millionaire inventor, movie producer, and oddball Howard Hughes. The role of Hughes – played by DiCaprio – suffered from OCD and other debilitating mental illnesses at a time where there was no real medical understanding for them, and Dicaprio played this shifty feeling with subtle anxiety throughout. In spite of fame, success, and love affairs with stars like Katharine Hepburn, ultimately Hughes would push everyone away as his mental health spiralled out of control. DiCaprio is heartbreaking and unlikeable all at the same time in the role.
2. Once Upon a Time in Hollywood (2019)
Directed by Quentin Tarantino
It’s no mistake that the top two choices on this list are of DiCaprio being ridiculous. It didn’t seem to be his natural comfort zone, but it arrived: turns out, he’s got a real talent for comedy. Featuring characters inspired by the 1969 Manson family murders, DiCaprio is Rick Dalton, a whisky-sour-drinking, down-on-his-luck cowboy TV actor. There’s something so perfect about his comic timing and delivery in this film, and his bratty, kinda-dumb-guy schtick, which sees him alternately drinking, yelling, and crying his way through the end of his career. This film marks the start of our new favourite “funny Leo” era – give him a flamethrower and watch him go.
1. The Wolf of Wall Street (2013)
Directed by Martin Scorsese
A brilliant, blackly comic deconstruction of the “greed is good” spirit, you could say Scorsese brings DiCaprio’s real-life persona to the screen – using his bombastic charm and obnoxious party boy rep to great advantage in The Wolf of Wall Street. The notoriously provocative story of Jordan Belfort, a white-collar penny stocks fraudster who scammed thousands of ordinary people and made a fortune while doing it, would be a shadow of itself were it not for DiCaprio’s chaotic egotism and self-aggrandising voiceover. He captures the empty sheen of this high-end luxury lifestyle and the moral rot beneath with gusto.
His would-be apologetic resignation speech, turning halfway through into a locker room pep talk ending in his defiant proclamation: “I’m not leaving! I’m not f***ing leaving!” is an all-timer. And don’t get me started on the physical comedy of the Quaaludes scene. This film truly proved he could do it all – sincere, callow, cruel, and hilarious. His range is remarkable, and it’s what makes him one of the great actors of his generation.
