Leonardo Dicaprio’s Best Movies: Are you a fan of the talented and handsome Leonardo Dicaprio? Read on for a list of some of his most amazing works.
He is both one of the most adored romantic leads in film history and one of the worst villains of the 20th century. (For what it’s worth, Jack, we won’t let go.) He has performed Shakespeare and has been mauled by a bear, which at least earned him an Oscar. Despite being one of the greatest actors working today, Leonardo DiCaprio has only completed 29 movies in his three decades as a superstar. (For comparison, Tobey Maguire, a fellow Pussy Posse alumnus, has amassed almost 40 acting credits in films.) But the actor is being rewarded for his exceptional selection skills. The majority of Leonardo DiCaprio’s films are incomparable, making it challenging to rank them. Nonetheless, what are Leonardo DiCaprio’s best movies?
Leonardo DiCaprio’s Best Movies
List Of Leonardo DiCaprio’s Best Movies
Here is a list of the top-ranked Leonardo DiCaprio films that are no less than a masterpiece and should be definitely on your watch list:
20. The Quick And The Dead

DiCaprio played the lead in the Sharon Stone-led western The Quick and the Dead, which was released not too long after his breakthrough performance in What’s Eating Gilbert Grape. Although the film itself may have been a dud, it has since gained cult status, and DiCaprio shines as “The Kid,” a gangly would-be gunfighter who doesn’t meet such a horrible end.
19. The Beach

In this Danny Boyle cult favorite, young Leonardo DiCaprio plays Richard, an American traveler. He is traveling to Thailand in pursuit of “something more beautiful, something more exciting, and something riskier.” Richard and his friends set sail for a hidden island utopia armed with a treasure map obtained from a local madman, but they quickly discover that paradise isn’t all it’s cracked up to be. In The Beach’s notoriously surreal third act, Richard is pushed into sociopathic craziness. DiCaprio gives it his best, cutting through the exaggerated chaos to weave a story that is exciting to watch.
18. Don’t Look Up

As Dr. Randall Mindy, a nebbishy astronomer caught up in a frenzy of deceit and disappointment as a planet-killing comet sets a collision path for Earth, DiCaprio leads the star-studded cast of this Adam McKay comedy. Although the movie is billed as a comedy, DiCaprio discovers emotional undertones in the narrative and gives a tragicomic performance as a fine man who is misled by end-of-the-world temptation. The actor gives a quieter performance than we’re used to seeing from him. But don’t worry—he still has time for a typical Leo freak-out when he loses his composure in front of Cate Blanchett and Tyler Perry’s portrayals of cable news anchors. Not just ‘Don’t Look Up’, here are the Top 25 Comedy Movies on Netflix that will leave you in stitches. And, while talking about movies on End of World, how could we forget to mention that we have created a special segment on Top 25 Movies On The End Of The World that are must-watch?
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17. Romeo And Juliet

It’s difficult to hold a young person responsible for crying excessively during a film about teenagers who tragically mess up a hilarious prank on their parents, leading to both of their deaths—especially when paired with Claire Danes, the most skilled weeper of her generation. However, if he had given us a little less of the “I defy you, stars!” line, this Baz Luhrmann-produced spectacle may have surpassed The Great Gatsby on the list. This movie’s sweaty, molly-fueled ballroom sequence paved the way for The Great Gatsby’s iconic scene.
16. Shutter Island

DiCaprio plays Edward “Teddy” Daniels, a U.S. Marshal sent to a spooky, secluded psychiatric facility on an island. He is here to investigate a missing patient with his new partner Chuck Aule (played by Mark Ruffalo) in Scorsese’s 2010 suspenseful psychological thriller. Of course, it turns out that’s not actually the case. Leo gives a nuanced portrayal of a neurotic man whose biggest mystery to solve is his own mind. Besides, this movie has one of the best twist endings of all time. Watch it on Amazon Prime.
15. The Great Gatsby

You could probably say this about a number of DiCaprio’s performances, but Jay Gatsby seems like the kind of role that was tailor-made for him. With a sleek haircut and a great deal of insecurity simmering beneath the surface, it’s not surprising that Leo got right into the character. (Also Read: 20 Hollywood Teenage Romantic Movies To Remind You Of The Magic Of Young Love)
Leonardo DiCaprio’s Best Movies
14. This Boy’s Life

DiCaprio’s breakthrough role on the big screen came as the real-life Toby Wolff, whose memoir about childhood pain and home struggles served as the inspiration for Michael Caton-Jones’ drama. It debuted eight months before his Oscar-nominated performance in What’s Eating Gilbert Grape. When Dwight, played by Robert De Niro, moves in with young Wolff and his mother (Ellen Barkin), he immediately turns their house into a battleground. The young Wolff, Leonardo DiCaprio engages in physical and verbal combat with Dwight. DiCaprio demonstrated that he was destined for the spotlight by evincing the intensity, range, and depth of emotion that he’d later develop. He exudes a determined fierceness that he wears like a suit of armor, designed to protect him from the slings and arrows (and wallops) of De Niro’s evil father figure.
13. What’s Eating Gilbert Grape?

This is where the actor who would quickly establish himself as one of the all-time greats of his generation was first really noticed by audiences and critics. It’s DiCaprio’s “star-is-born” moment, and the Academy would acknowledge it by giving Leo his first Oscar nomination. DiCaprio is devastating and moving in equal measure as Arnie, the sweet, mentally disabled younger brother of Johnny Depp’s aimless Gilbert. He delivers a powerful performance without ever hitting any of the wrong notes that so many other young performers might have fallen prey to. It’s technical wizardry of method intensity, gut-wrenching empathy, and conjuring magic. Yes, Depp was apparently the main draw in this movie. But when you left the theater, DiCaprio had your attention.
12. Inception

It’s a dream within a dream (within a dream!), and DiCaprio delivers another outstanding performance. DiCaprio leads an ensemble cast as Dom Cobb, a man who commits mental heists by intruding into people’s dreams and extracting information from their subconscious, in Christopher Nolan’s mind-bending thriller. He has particularly strong chemistry with co-star Elliot Page as the two explore the mental abyss together, delving into Dom’s own trauma while infiltrating other people’s thoughts. It’s an action movie in the DiCaprio mold, and it’s fantastic. (And the top spins on…)
Leonardo DiCaprio’s Best Movies – A Few More
11. Blood Diamond

Edward Zwick’s epic might have been just another treasure hunt in Africa, lost amidst the other movies from the continent that attempted to make an impact. However, DiCaprio’s portrayal of diamond smuggler Danny Archer, a man with neither a country nor a moral compass, marked a career high point (at the time). DiCaprio rejects the film’s desperate need for a redemption story, portraying Archer as the slimeball that he really is. Watch it on Amazon Prime. And, don’t miss our feature on What’s new on Amazon Prime this month!
10. Gangs Of New York

After becoming a household name thanks to Titanic, Leonardo DiCaprio wisely chose to collaborate with some of the most celebrated directors in American cinema. This included starring in Martin Scorsese’s epic historical drama about the Protestant-Catholic battles for control of Manhattan in the mid-1880s. In this complex, bloody epic about the social and religious conflicts that helped shape the fabric of New York City and, by extension, the nation, Leonardo DiCaprio plays Amsterdam Vallon, a young man seeking vengeance for the murder of his father against Daniel Day-Lewis’ Bill the Butcher. DiCaprio and Cameron Diaz handle their love scenes with ease, but the actor genuinely exhibits a passion to rival the savagery of Scorsese’s set pieces in his moments with a towering Day-Lewis.
9. The Revenant

Alejandro Gonzalez Inarritu’s stunning film is probably best known as the movie in which Leo gets mauled and chewed to ribbons by a big grizzly bear. DiCaprio is undoubtedly committed to the severe physicality of the role of a hardy hunter from the 19th century. It is unquestionably the most demanding project he has ever taken on. While the movie is breathtakingly beautiful, there are times when it feels like a slow-burning slog as Glass struggles to survive in the cold West, fueled only by the blazing fire of anger and revenge that smolders within him. DiCaprio may have viewed it as his “dirt beneath the fingernails” atonement for The Great Gatsby’s flashy jazz and champagne. At least it finally won Leo his Oscar for Best Actor.
Leonardo DiCaprio’s Best Movies List
8. Django Unchained

Since he had already flourished under the guidance of Spielberg, Scorsese, Cameron, Nolan, Luhrmann, Boyle, Eastwood, and Mendes, DiCaprio gave Django Unchained, directed by Quentin Tarantino, a standout performance that stole many a scene. Calvin J. Candie, played by Leonardo DiCaprio, is a despicable 19th-century southern plantation owner who owns Kerry Washington’s Broomhilda. This made him the main target of Jamie Foxx’s vengeful freed slave. Candie is an over-the-top upper-crust with low morals and he acts as a captivatingly loathsome contrast to Foxx’s righteous avenger. He has slicked-back hair, a devilishly pointed goatee, and a shit-eating sneer that conceals his cold, vicious sociopathy. It’s an exciting affirmation that DiCaprio, despite being a leading guy, is perfectly suited for villainy.
7. The Aviator

In the extravagant biopic The Aviator, which was his second collaboration with Scorsese, DiCaprio portrayed renowned aviation mogul, director, and reclusive Howard Hughes. The actor brings a larger-than-life magnetism to the historical figure and whose ambitions were as outsized as his love of women was unquenchable. DiCaprio’s Hughes is another in a long line of troubled Scorsese protagonists striving for greatness while battling self-destructive impulses. DiCaprio achieves the grandeur of Hughes’ personality and life by first exuding oversized swagger and later manic lunacy. It’s possibly Caprio’s most underappreciated performance to date.
6. The Revolutionary Road

The Revolutionary Road is frequently overlooked, most likely because Leonardo DiCaprio gives a challenging performance in it. But among his best works is the picture of Frank Wheeler, a former free spirit whose originality is gradually destroyed by suburban Connecticut life. Together with Kate Winslet, they deliver heartbreaking performances as a couple fighting to preserve their identity. The film’s enemy, which subtly tears the two apart, is the push and pull of a life that has been perfected.
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5. Titanic

Again, for the benefit of those in the back: Jack had enough room on that goddamn door! Who knows how his career could have developed if that tragic accident hadn’t happened? DiCaprio is authentically DiCaprio in Titanic. Given the film’s size and technical innovations, two incredibly endearing leads were necessary to give the movie a human feel. In fact, Leo did it. Nothing further or minimal. It is fundamentally human. And for just this reason, more than twenty years after Jack’s passing, it still hurts so much. We’d like to see him in person. Few young actors at the time or of his age could have so successfully captured our hearts. Loved watching Titanic? Then you must watch these Best Sad Romantic Movies Of All Time that will make you cry & touch your heart.
4. The Departed

2006 was a memorable year in cinema. Although he was nominated for an Academy Award for Best Actor for his performance in Blood Diamond, DiCaprio carried much of the weight in this gritty ensemble of corrupt police and good villains. He portrays Billy Costigan, a state agent who infiltrates the underground. Now that they have collaborated three times, Martin Scorsese and Leonardo DiCaprio are regarded as one of the best and most natural pairings in contemporary cinema.
3. Catch Me If You Can

Leonardo DiCaprio will always be associated with Titanic, but it is more likely that he wants us to remember him for Catch Me If You Can. This movie was released five years after Titanic, during which time Leo produced some of his weakest works. But in Catch Me If You Can, Leo plays up the charm and allure with the cunning wink of a con artist. Do we really know Leo, or are we just pretending? In fact, honestly, it doesn’t even matter if the film is based on a true story because his performance is so captivating and complex. Loved watching Catch Me If You Can? Then we are sure you will love these Top 20 Motivational Hollywood Movies to inspire you to never give up.)
Leonardo DiCaprio’s Best Movies
2. The Wolf Of Wall Street

We really can’t imagine shouting nonstop for hours at the top of our lungs. But Leo, whose veins are about to burst, has more energy than the entire cast combined for the role. Besides the yelling, drugs, arrogance, and depravity, DiCaprio does an excellent job of tracing the development of Belfort’s character. As the unreliable narrator, DiCaprio once again uses his charm to deceive the audience while trying to convince them that Belfort isn’t such a terrible person. His persuasiveness nearly makes you want Belfort to succeed, while also urging you to laugh at him rather than with him.
1. Once Upon A Time In Hollywood

It’s not surprising that Brad Pitt received a lot of attention for Quentin Tarantino’s ninth movie. He had his best performance in years and was single, sober, and shirtless for a scene. But if he was the focus, DiCaprio was the emotional heart of the movie. We were in tears watching him play the role of Rick Dalton, a fading actor who has a drunken death grip on his past fame. Yes, tears from a Quentin Tarantino movie. He was intelligent and charming, as well as self-loathing but never pitiful. In fact, he could even be downright funny at times.
In conclusion, Leonardo DiCaprio has undeniably left an indelible mark on the world of cinema through his outstanding performances in some of the best movies of our time. From his breakthrough role in “Titanic” to his captivating portrayal of Jordan Belfort in “The Wolf of Wall Street” and his powerful performance in “The Revenant,” DiCaprio has consistently proven his immense talent and versatility as an actor. His dedication to his craft, coupled with his ability to immerse himself in complex characters, has earned him numerous accolades and the adoration of millions of fans worldwide. Leonardo DiCaprio’s filmography stands as a testament to his exceptional skills and his contribution to the art of storytelling on the silver screen will continue to resonate for generations to come.