Thanks to the double whammy of a hip, modernized adaptation of Romeo and Juliet and a version of Romeo and Juliet set on the Titanic, Leonardo DiCaprio has been one of the world’s biggest movie stars since the late ‘90s. In the decades that followed, DiCaprio gave acclaimed performances in such films as The Aviator, The Revenant, and Once Upon a Time in Hollywood.
The actor’s awards cabinet has amassed an Academy Award, a BAFTA, and three Golden Globes (among a bunch of other honors and accolades). He’s known for recurring collaborations with renowned filmmakers like Martin Scorsese and Quentin Tarantino, but he’s also had one-off collaborations with directors like Steven Spielberg and Christopher Nolan.
Christopher Nolan
Now one of the most popular filmmakers working today, Christopher Nolan initially broke out with the curious low-budget neo-noir psychological thriller Memento. He later revolutionized the superhero genre (and blockbuster cinema in general) with the gritty realism of The Dark Knight trilogy.
Nolan honed his particular brand of breathtaking IMAX action sequences in the Batman movies before casting DiCaprio as the lead in his high-concept sci-fi epic Inception, a heist movie about stealing ideas from people’s minds while they’re asleep.
Baz Luhrmann
Renowned for his dazzling visuals, Moulin Rouge! director Baz Luhrmann has worked with DiCaprio on a couple of occasions. They first collaborated in the ‘90s when the actor was just starting out and later reunited in the 2010s when DiCaprio was the king of the world.
DiCaprio played the star-crossed male lead in Romeo + Juliet, Luhrmann’s modernized adaptation of the Shakespeare classic, and the title role in The Great Gatsby, Luhrmann’s big-budget adaptation of the Fitzgerald classic.
Sam Raimi
Thanks to his groundbreaking debut feature The Evil Dead, Sam Raimi is a legend of horror cinema. But he’s occasionally stepped outside the horror genre to helm acclaimed entries in other genres.
His groundbreaking Spider-Man trilogy changed comic book movies forever, while The Quick and the Dead is a fun revisionist western featuring a young DiCaprio among a star-studded cast including Sharon Stone, Gene Hackman, and Russell Crowe.
Alejandro G. Iñárritu
DiCaprio finally won an Academy Award for his turn as a frontiersman who survives a bear attack in Alejandro G. Iñárritu’s bleak western epic The Revenant.
The movie utilizes a lot of long takes, calling back to the style of Iñárritu’s previous Oscar-winning gem Birdman, which was shot and edited to look like a single two-hour take.
James Cameron
One of the most revered action filmmakers in the world, James Cameron is the acclaimed creator of the Terminator franchise. He also created a big chunk of the Alien franchise’s mythology for his game-changing sequel Aliens.
Cameron directed DiCaprio alongside Kate Winslet in Titanic, a movie so successful that they instantly became two of the biggest stars in the world. A big-budget romantic melodrama based on a historical tragedy was naturally expected to bomb, but Titanic defied the skeptics to become the most successful movie of all time. Cameron repeated this trick a decade later with Avatar.
Clint Eastwood
Clint Eastwood became an iconic Hollywood movie star throughout the 1960s and 1970s before successfully transitioning into directing. Eastwood is just as renowned for his directorial work – Unforgiven, Mystic River, Gran Torino, etc. – as his acting performances.
Eastwood directed DiCaprio in a biopic of former FBI director J. Edgar Hoover, titled J. Edgar. The film received mixed reviews, but DiCaprio’s performance as Hoover was consistently praised.
Quentin Tarantino
Throughout the 2010s, DiCaprio joined Samuel L. Jackson, Uma Thurman, and Tim Roth in Quentin Tarantino’s regular company of actors. DiCaprio has played two vastly different characters in the Tarantino oeuvre.
In Tarantino’s slavery-era spaghetti western Django Unchained, DiCaprio played sadistic plantation owner Calvin Candie. In his ‘60s-set film industry fairy tale Once Upon a Time in Hollywood, DiCaprio played insecure TV cowboy Rick Dalton, earning him an Oscar nod for Best Actor.
Ridley Scott
When DiCaprio worked with Ridley Scott, it resulted in one of the director’s lesser-known movies. Body of Lies is a forgettable spy thriller starring DiCaprio alongside Russell Crowe.
Although Body of Lies isn’t a particularly strong film, Scott has helmed some of the greatest movies ever made throughout his decades-long career, like Alien, Gladiator, Blade Runner, and Thelma & Louise (to name just a few).
Steven Spielberg
As the director who brought Indiana Jones, E.T., and the dinosaurs of Jurassic Park to the big screen, Steven Spielberg is one of the most celebrated filmmakers in Hollywood.
DiCaprio played legendary con man Frank Abagnale, Jr. in Spielberg’s hilarious cat-and-mouse caper Catch Me If You Can. Tom Hanks makes a great comedic counterpoint to DiCaprio as the stuffed-shirt FBI agent on his tail.
Martin Scorsese
At the turn of the 21st century, DiCaprio replaced Robert De Niro as Martin Scorsese’s go-to leading man with his turn as a young gangster out for revenge against Daniel Day-Lewis’ Bill the Butcher in Gangs of New York.
Since then, DiCaprio has played Howard Hughes in The Aviator, an undercover Boston cop in The Departed, a U.S. Marshal questioning his identity in Shutter Island, and amoral stockbroker Jordan Belfort in The Wolf of Wall Street. DiCaprio and Scorsese are currently working on Killers of the Flower Moon, which will be the first Scorsese movie to feature both DiCaprio and De Niro.