Leonardo DiCaprio Movies You Need To Rewatch

The man is a literal movie-chameleon

Leonardi DiCaprio is a man that needs no introduction. You know his name, his face, his advocacies and his movies. But despite the decades he has spent on screen and on magazine covers, the world still seems to not have gotten enough of him. And really, how could we mere mortals say “Enough!” when one of the world’s most talented actors is willing to show us more? And if we’re being really honest, it’s not like we haven’t spent nights in bed re-watching his older stuff, too.

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What’s Eating Gilbert Grape (1993)

A poignant yet devastating story partnered with stellar acting make for one of the industry’s most enchanting films. What’s Eating Gilbert Grape shoved Leo to the world of film in the best way possible. It wasn't his first foray into the big screen, but his portrayal of Alfie, a mentally disabled boy, got everyone’s attention.

Set in the small town of Endora, Gilbert Grape must take care of his little brother Arnie as his overweight mother is unable to. But while this alone sounds like a difficult life to stomach, Gilbert marches on. And through love, heartbreak and some soul searching, the family eventually finds peace.

Romeo + Juliet (1996)

With very few changes made, Romeo + Juliet pretty much retained the original Shakespearean dialogue of one of the most classic love stories known to man. And while this arguably didn’t match up with the more modern setting of Verona Beach, which was riddled with gang violence between opposing mafia empires, it still had us glued to the screen.

The chemistry between Leo and Claire Danes was jumping off screen and the overall environment of the film captured the 90s like almost nothing else. The neon crucifixes, the skylines and the fireworks provided an eruption of light that just lit up the scenes. The soundtrack—and Leo’s baby-faced confessions of love—were just the cherry on top.

Titanic (1997)

Titanic started the love story between one Leonardo DiCaprio and one Kate Winslet, which has been adored by generation after generation. The premise of the film, that of an unhappy rich girl and a life-living pauper, has been overdone countless times, but what happened on the Titanic between Rose and Jack holds a special place in everyone’s hearts.

James Cameron’s masterpiece will never get old. From the build-up of Rose and Jack’s love story and all that opposed it to the complete and utter devastation in the end, you’ll never find yourself asking “Could this movie have given me more?”

Catch Me If You Can (2002)

Leo as a leading man to a beautiful leading woman is never a mistake, but Catch Me If You Can proved that the actor could mix it up against an equally talented Tom Hanks.

Part period piece, part drama and part chase film, Catch Me If You Can took us on a thrilling run in the capture of the youngest person to ever make it to the FBI’s 10 Most Wanted List. The cat and mouse plot, Leo’s unrelenting portrayal of Frank Abagnale and the oddly satisfying slow-burn of the film make it a breathtaking piece to watch.

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Blood Diamond (2006)

While critics’ reviews of Blood Diamond fall on different spots of the love/hate spectrum, the one thing that everyone seems to agree on is the fact that the actors’ performances are spot on. All action, drama and excitement, the film forces provocative thought on usually unquestioned methods.

The fictional tale, which is only inspired by true facts, brings together three individuals of different backgrounds. With a fisherman carrying a devastating past, a journalist in search of a big break and a criminal with his eye on a large prize, Blood Diamond is equal parts thrilling, eye-opening and brutal.

Revolutionary Road (2008)

Bringing back one of Hollywood’s most beloved pairings, Revolutionary Road captured Leo and Kate in a more mature—and arguably realistic—light.

While the story itself was painful to watch as it shows the fall of a seemingly perfect suburban family as they lose love and interest, it cuts down to the core of true human emotion. Kate’s April is exhausted, emotionally finished and unforgiving while Leo’s Frank is settling in an often delirious state.

Shutter Island (2010)

Proving that he can do stylized psychological thrillers as well as dramas, Leo tackles the role of Teddy Daniels in this Martin Scorsese classic.

Plagued with past images of a Nazi concentration camp and visions of his dead wife, federal marshal Daniels must figure out what happened to an escaped murderer while on Shutter Island with his partner Chuck Aule. But the real thrill of the film is not in the shallow storyline, but in the underbelly of the correctional facility—as well as Daniels’ mysterious motives.

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Inception (2010)

Because watching Inception just once will not give you the 360-view that you truly need to appreciate the film, it is completely forgivable that you take it up a second, third or sixth time. The story is complex yet imaginative, entertaining and wholly coherent.

Using a mix of action, emotion and mind-boggling theories, Inception is a film that captures imagination from the opening scene. What follows is a journey that is mysterious, riveting and beautiful to watch unfold. 

The Wolf Of Wall Street (2013)

Director Martin Scorsese hit it out of the park once again with The Wolf Of Wall Street, headed on screen by Leo in spectacular fashion as he took on the role of Jordan Belfort. Many still believe that Leo should have won the Academy Award for his portrayal—a belief that is supported by every scene he blessed.

While it is almost three hours long, you’ll find yourself wondering where the time went each and every time you put on The Wolf Of Wall Street. And despite the obvious use of drugs, illegal trade and sex, it is topped off with comedy that is refreshing and sometimes even sweet. 

The Revenant (2015)

In a performance that was—in a word—committed, Leo finally nabbed his Oscar for Best Actor thanks to The Revenant. His stellar acting, partnered with Emmanuel Lubezki’s beautiful cinematography and Alejandro González Iñárritu’s genius direction, made it one of the year’s most must-watch films.

The grueling journey of Hugh Glass as he is forced to survive in the wild is almost unwatchable at points, but Leo’s portrayal will have you glancing at the screen despite this. The battle with the bear, the night spent inside a dead animal carcass—these are scenes you cannot erase from memory.

Leonardo DiCaprio is an actor that shines above and beyond the glittering stars of his generation. His movie roster is vast and unchallenged, just as his performances are memorable.

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Adie Pieraz

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Alex Lara

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