As Baz Luhrman and Leonardo DiCaprio unveil their second collaborative effort, The Great Gatsby to general audiences this weekend, it’s easy to let the nostalgia take over. It is a beloved story that has been read by teenagers in high schools all across the country for decades and has found a place in all our hearts.

Just like The Great Gatsby, Leonardo DiCaprio has also wormed his way into our hearts throughout his 24-year career. In honor of this remarkable pairing, we thought it would be nice to take a look back at the Leonardo DiCaprio movies that turned the actor into the person we know and love today.

Dom Cobb in ‘Inception’

Leonardo DiCaprio inception

Inception, Chris Nolan’s smash hit from 2010, created one of DiCaprio fans’ favorite and one of the most important roles of his career. In his first film post-The Dark Knight, Nolan made an impression on general audiences, and choosing DiCaprio to lead the film was one of the smartest moves he could have made. Equal parts complicated and endearing, the heart at the center of Inception belongs to the struggle that Leo depicts so effectively as Cobb chooses his own reality.

Jack Dawson in ‘Titanic’

Leonardo DiCaprio HD photo Titanic Jack Dawson

In arguably his most well-known role to date, Leonardo DiCaprio shone through the wide-eyed innocence of Jack Dawson. This character gave life to an event that few people fully understood. History remembers the Titanic as an infamous tragedy, and due reverence is paid to its victims, but Jack Dawson became the face of the many unfortunate victims of unfortunate circumstances in this Oscar-winning film from James Cameron.

Calvin Candy in ‘Django Unchained’

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If there’s one thing Tarantino does well, it’s write enchanting villains. Django Unchained was no different. It’s a shame that he didn’t get more recognition, but Calvin Candy is one sickeningly sweet bad guy. The twisted, stringy slaveowner in Tarantino’s spaghetti western is the perfect foil to Django’s hard-edged, street-wise freed slave. If there could be a better dichotomous duo, I would hang up my holster and saunter out of town…

Billy Costigan in ‘The Departed’

The Departed Leonardo DiCaprio Billy Costigan

When an actor lands a partnership with an estimable director like Martin Scorcese, and manages to make an impression enough to land leading roles in four more of his films, you just know that a true talent has found its match. In their third project together, The Departed, DiCaprio tackled the role of Billy Costigan, a young member of a revered mob family in South Boston that becomes a double agent, leaking precious secrets to the Boston police. Most notably, DiCaprio managed to master the tough accent of a South Boston native as well as that of a South African diamond aficionado in the same year. Impressive doesn’t even begin to cover it.

Frank Abagnale Jr. in ‘Catch Me If You Can’

Leonardo DiCaprio Catch Me if You Can

The imaginative tale of a con artist that managed to swindle millions of dollars by posing as a pilot, a doctor, and a legal authority gave Leo an opportunity to play on the light-hearted side of things. More often than not, his choices lean toward the dramatic, and while this role had no shortage of drama, it also demanded playfulness and fun.

Romeo Montague in ‘Romeo + Juliet’

Leonardo DiCaprio Romeo + Juliet

In the world of legendary romances, there is none more well-known than Romeo and Juliet. In their first film together, Baz Luhrman and Leonardo DiCaprio managed to spin this classic tale into one of the most successful re-imaginings of a Shakespeare tale to date. Placing the original dialogue in a modern setting breathed new life into the story without stripping it of its most valuable asset. Leo’s performance raised him to heartthrob status in the mid-late 90s; a distinction he held until his roles of the early 2000s propelled him to the epitome of Hollywood elite.

Jim Carroll in ‘The Basketball Diaries’

Leonardo DiCaprio Basketball Diaries

The Basketball Diaries provided a unique challenge to a young actor on the rise. In a departure from his otherwise squeaky clean image at the time, this horrific tale of a talented basketball player turned drug addict showed the range that DiCaprio could muster, and it proved to any nay-sayers (if there were any) that this fresh faced youngster was a talent to be reckoned with. We include it as a favorite because it’s hard not to be amazed at the talent such a young man can display, especially with such dark, gritty subject matter.

Arnie Grape in ‘What’s Eating Gilbert Grape’

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Perhaps the role that established his reputation as a legitimate young actor, Arnie Grape is equal parts charming, challenging, and engaging. It would have been easy to turn the character into a caricature of that level of mental illness, but Leo managed to balance respect and accuracy without falling too far in either direction, and to strike that balance at the rather young age of 19 is the sign of a true talent, and marked him as one to watch.

J. Edgar Hoover in ‘J. Edgar’

Leonardo DiCaprio J Edgar Hoover

While not a fan favorite of his films for sure, no one can deny the talent on display as DiCaprio portrays the man credited with bringing the Federal Bureau of Investigation to prominence during his 50 years of service, J. Edgar Hoover. He managed to bring vulnerability to an otherwise turgid, stodgy man, while also painting him as a strong leader, more than capable of handling the demands of his office.

Danny Archer in ‘Blood Diamond’

Leonardo DiCaprio Danny Archer Blood Diamond

The story surrounding Danny Archer and the controversial diamond business provided the perfect platform for DiCaprio to show off his prestigious talent. While some question the accent he affected to make the role as authentic as possible, even more praise the actor for having the guts to tackle such a momentous obstacle, not to mention also attempting a South Boston accent in a film released the same year. Blood Diamond beautifully displays the dedication that DiCaprio has to his craft.

What is your favorite Leonardo DiCaprio movie and character?

Edited by Brandi Delhagen