10 Best Directors Leonardo DiCaprio Has Worked With, Ranked

Leonardo DiCaprio is one of Hollywood’s most storied actors. His career began in the 1980s on sitcoms, with a breakout role in the hit ABC sitcom Growing Pains. From then on, DiCaprio was seen as one of the new fresh faces in Hollywood, and he has appeared in numerous box office hits over his storied career.

Those hits were also directed by some of Hollywood’s most famous directors, from Danny Boyle to the legend himself, Martin Scorsese. In fact, it was actually kind of shocking that, in all the movies he acted in alongside these storied directors, that it took years for him to get his first Best Actor Oscar, which came in 2016 with The Revenant. But, that topic is for another day. As for this piece, we’re going to list the best directors who brought out the best in DiCaprio, and helped make him the legendary actor that he is today. So, without further ado, let’s dive in.

10

Edward Zwick

What do war, politics, and diamonds have in common? They couldn’t be any different than peanut butter and salmon, but they came together nicely to create one of the most underrated political war thrillers. That movie was Blood Diamond, directed by Edward Zwick and starring DiCaprio as Danny Archer, a Rhodesian gunrunner who was captured and incarcerated in Freetown during the Sierra Leone civil war.

Blood Diamond was a scintillating thriller that hit all the right notes, thanks to the directing of Zwick and DiCaprio’s captivating performance. For this, he received five Oscar nominations, including the Best Actor award that would elude him until 2016. It’s a shame Blood Diamond has kind of been forgotten, which, as we’re writing this, gives us the urge to go back and stream this 2000s gem.

9

Adam McKay

Director Adam McKay has a knack for getting the best comedic performances out of the actors he directs. Comedy is McKay’s bread-and-butter, a genre he built his resume on, especially with his frequent collaborations with Will Ferrell. In 2021, he decided to make a black comedy satire about the possible future events of the end of the world and the current state of politics, and he tapped DiCaprio to lead a stellar ensemble cast in the 2021 gem Don’t Look Up.

Here, DiCaprio stars alongside Jennifer Lawrence as two astronomers who try in vain to warn the world of a comet that will destroy the world. DiCaprio was tremendous in the role, and McKay used his comedic genius to tap into media indifference to the coming threat of climate change. As iconic as Anchorman and Talladega Nights were, Don’t Look Up was McKay at his best, thanks in large part to DiCaprio’s performance.

8

Danny Boyle

While we know DiCaprio as part of the Mount Rushmore of Hollywood leading men today, back in 2000, while his star power was rising, he wasn’t quite there yet on the mountain of legendary actors. That took a huge leap forward with The Beach, directed by Danny Boyle, in a truly unforgettable performance.

Adapted from Alex Garland’s 1996 novel of the same name, The Beach finds DiCaprio as a backpacker who finds that paradise isn’t all that it seems when he arrives in Thailand. While the scenery was truly stunning, DiCaprio’s performance as Richard was truly remarkable, displaying a range that some didn’t think he had, and putting him on a path to making more impactful films. While The Beach was met with mixed reviews, it’s a cult classic today, with DiCaprio’s performance and Boyle’s dynamic directing.

7

Alejandro González Iñárritu

We know that some would question why Alejandro González Iñárritu would get the nod here over Steven Spielberg, and we get it. Catch Me If You Can was a tremendous film that launched DiCaprio’s film career into the stratosphere. However, we went with Iñárritu here because the only film DiCaprio worked with was so captivating, and so tremendously acted and directed, that it finally got him the coveted Oscar for Best Actor that had eluded him for years.

That movie was The Revenant, and that character was Hugh Glass, a frontiersman who went through a lot in 1823, including fighting a grizzly bear. While that scene will forever remain in internet meme history, it shouldn’t distract from just how stunning The Revenant was, both visually and story-wise. Iñárritu’s direction on The Revenant is still talked about to this very day, along with Emmanuel Lubezki’s iconic cinematography and DiCaprio’s unforgettable performance as Hugh Glass.

6

Baz Luhrmann

Back in the mid-90s, DiCaprio was just starting to enter his enchanting film career as one of Hollywood’s leading actors, especially after the Academy Award-nominating performance he did in 1993’s What’s Eating Gilbert Grape. So, for a followup, he teamed up with director Baz Luhrmann for a modern-day retelling of William Shakespeare’s Romeo & Juliet, which, to this day, is a cult favorite.

His performance as Romeo Montague was fascinating, and with Luhrmann’s direction, DiCapro really brought that character into the modern age. 17 years later, DiCaprio would team up with Luhrmann again for another iconic performance, this time as Jay Gastby in the historical romance drama The Great Gatsby. The direction, visuals, and performance, especially by DiCaprio, were all praised; and while that film has become somewhat overlooked today (especially given DiCaprio’s bounty of iconic films), it shows that whenever DiCaprio and Luhrmann team up, they always have that touch to make movie magic.

5

Steven Spielberg

We fooled you, didn’t we? Of course, Steven Spielberg was going to be here! He is, after all, part of the Mount Rushmore of iconic Hollywood directors, and in 2002, one of the titans of movie directors teamed up with the up-and-coming titan of A-list actors to help bring a semi-autobiographical book to life.

That book was Catch Me If You Can, written by Frank Abagnale Jr., who, on his 19th birthday, initiated cons that would make him millions, allegedly, as the truth is heavily disputed. Whether it was true or not, it still makes for a great movie, and Spielberg and DiCaprio, along with a great performance (as always) from Tom Hanks, brought this wild story to life in the film adaption of the book. Praised for its score and acting, Catch Me If You Can was like lighting in a bottle for both Spielberg and DiCaprio.

4

Clint Eastwood

It seems kind of odd to make a movie that depicted the career of J. Edgar Hoover, the legendary FBI director; but in 2011, Clint Eastwood tapped DiCaprio to play Hoover in the biographical drama J. Edgar. The pairing of Eastwood and DiCaprio also sounded a bit odd, but it turned out to be a great pairing of a living movie legend, and one that was making his legend.

J. Edgar, despite some flaws, is one of the best biographical dramas of the 2010s, despite its mixed reception when it was first released. DiCaprio really captured the spirit and tone of J. Edgar Hoover, and his performance, by far, was a tour-de-force as to what makes DiCaprio so special as an actor. It was as if Eastwood decided to let DiCaprio do what he does best; and, if that was the case, it was a great decision. J. Edgar should be more praised than it is today, as historical bluffs would absolutely love this movie. This is all thanks to Eastwood’s directing and DiCaprio’s mesmerizing acting.

3

Quentin Tarantino

Quentin Tarantino has a unique directing style that very few, if any, can replicate. So, in 2012, while most people were wondering with amusement if the Mayan prediction would come true, we were, at the same time, excited to see Tarantino and DiCaprio team up in Django Unchained, a revisionist Western that is often praised as one of the best revisionist Westerns ever made, especially due to Tarantino’s unique directing and DiCaprio’s magnetic performance.

Much like DiCaprio and Baz Luhrmann, it quickly became apparent that whenever Tarantino and DiCaprio, movie magic was soon to follow, and that was confirmed when, seven years later, the two hooked up again with the iconic Once Upon a Time in Hollywood, a period comedy-drama that is one of the best movies of the 21st century thanks to the magic that DiCaprio and Tarantino brought to the film.

2

Christopher Nolan

We honestly cannot remember a single bad movie Christopher Nolan has made, and yes, we’re including Tenet in this. Over his career, he has produced a countless number of iconic movies, including one in 2010, in which he teamed up with DiCaprio for a truly unforgettable performance. That movie was Inception, a mind-bending science fiction action film that is one of the best to ever do it.

There is a great reason as to why Inception was so widely celebrated. The dynamic cinematography; the visual effects that made you feel every bit as you were in those warped rooms with the cast; the stellar directing that turned a story that could have been cheesy into one that cannot be replicated by another director; and the acting of DiCaprio, who helped bring this story to life. Although they have (for now) only Inception, it was clear that the pairing of Nolan and DiCaprio is a winning formula. Here’s hoping these two Hollywood titans collab on a future classic.

1

Martin Scorsese

Much like Adam McKay was an important collaborator to Will Ferrell’s career, so was Martin Scorsese to Leonardo DiCaprio’s career. He’s the director that DiCaprio has worked with the most, with six films under their collective belts, and all of them iconic classics. Starting with 2002’s Gangs of New York, Scorsese and DiCaprio just had that touch to bring something special to the big screen.

We saw this to great effect in the early part of the 2010s, with 2010’s Shutter Island and 2013’s The Wolf of Wall Street, each movie bringing a different vibe, but both equally talented behind the camera and in front of it. In fact, it was nearly criminal that DiCaprio didn’t take home the Oscar for Best Actor with regard to any of the movies he collaborated on with Scorsese. They were that good, and we can’t wait until the next film featuring one of modern cinema’s most dynamic actor-director duos.