Best Leonardo DiCaprio Movies of All Time

Leonardo DiCaprio is one of the most beloved actors in movie history. As one of the greatest actors of today, he is extremely selective of the movies he plays in and has done only 29, which is paying off. Here at TechTrends, we decided to make a list of the best Leonardo DiCaprio movies of all time, as he is a historical actor.

Leonardo DiCaprio has been one of the best actors for more than 20 years. Notwithstanding growing up onscreen, we can see that there is an unknowable quality to this great man. The Oscar-winner movie star has tried to work with some of the best filmmakers of modern time. Starting from What’s Eating Gilbert Grape 1993, for which he got his first nomination for Academy Award when he was 19. DiCaprio has been nominated for the Oscars eight times; seven were as an actor and one as a producer. Therefore, for a career like that of DiCaprio, it is always a perfect time to go deep into his filmography.

There are only a few actors who make consistently fascinating choices when it comes to movie choices; DiCaprio is one of them. It is hard to make a list of the best Leonardo DiCaprio movies of all time as most of them are incomparable. Even the fact that he plays in them makes those movies stand out. TechTrends, however, did try and did make a list of his best movies. So, let’s get into it without further ado.

Best Leonardo DiCaprio Movies of All Time

Leonardo DiCaprio is known as one of the most talented and sought-after actors in Hollywood. However, we cannot deny that he knows how to choose great movies to play in. although he might have rejected some great movies, almost every movie he acted in ended up being a great one. It was hard to narrow down the best Leonardo DiCaprio movies of all time. Here is the list set in chronological order; so, let’s get to it.

What’s Eating Gilbert Grape 1993

  • Genre: Drama
  • Director: Lasse Hallström
  • Stars: Leonardo DiCaprio, Johnny Depp, Darlene Cates, Juliette Lewis
  • Rating: Rotten Tomatoes 90%, IMDb 7.7

Featuring in the movie What’s Eating Gilbert Grape, Leonardo DiCaprio performed one of his most mind-blowingly amazing roles. The movie is a drama that takes place in a small town in which Johnny Depp takes care of his morbidly obese mom and his younger brother, Leonardo DiCaprio, who is mentally challenged. Moreover, the chemistry shown between DiCaprio and Depp is incredibly convincing, making the audience believe that these two characters are truly brothers. This is indeed one of the best Leonardo DiCaprio movies of all time. Aged 19, DiCaprio got his first nomination for Academy Award as Arnie Grape, the mentally-challenged brother. In this daring role, he proved he is an actor to be reckoned with. In addition, he got his first Golden Globe Award nomination for this movie as well. Not bad at all.

This movie presents a dysfunctional family that is trying to function in the best way they know how, portraying true compassion. In addition, it portrays the importance of support in times of need, when somebody you love is suffering from a mental disorder.

Titanic 1997

  • Genre: Drama
  • Director: James Cameron
  • Stars: Leonardo DiCaprio, Kate Winslet
  • Rating: Rotten Tomatoes 87%, IMDb 7.9

James Cameron created an unforgettable epic romantic drama movie which is now considered one of the best Leonardo DiCaprio movies of all time. Titanic is crafted flawlessly, constructed intelligently, and acted strongly. As for the plot of the movie, it involves a woman named Rose, who is on the verge of sailing to her doom as she got engaged to a rich man by force. Filled with hatred for this prospect, she even tries to take her life. However, she is saved by Jack, portrayed by DiCaprio, with whom she falls in love. Ultimately, we all know what the outcome of Titanic is. The director, however, takes us beyond that and puts us in the skin of the ones who perished and the ones who survived. He also reminds us that no matter who we are, we are all in the same boat.

DiCaprio played his role with Charisma, with the movie that won 11 Academy Awards making him permanent global superstardom. He went from a respected movie star to a worldwide-known actor. He got his second Golden Globe Award nomination for his performance as well as his second nomination for a Screen Actors Guild Award.

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Gangs of New York 2002

  • Genre: Crime/Drama
  • Director: Martin Scorsese
  • Stars: Leonardo DiCaprio, Daniel Day-Lewis, Cameron Diaz, Liam Neeson
  • Rating: Rotten Tomatoes 72%, IMDb 7.5

The next one of the best Leonardo DiCaprio movies of all time is Gangs of New York. The 47-year-old actor collaborated with Martin Scorsese for the first time. Moreover, the story happened in the mid-1800s in Manhattan and crime lord William Cutting, also called Bill the Butcher” runs the place. He saw his father being killed by Bill while he was a child. So, he kept the knife to utilize it for his revenge on his father’s death. DiCaprio showed a big brawny performance.

The Departed 2006

  • Genre: Crime/Drama
  • Director: Martin Scorsese
  • Stars: Leonardo DiCaprio, Vera Farmiga, Jack Nicholson, Matt Damon, Mark Wahlberg
  • Rating: Rotten Tomatoes 90%, IMDb 8.5

DiCaprio featured in Martin Scorsese’s Oscar-winning Best Picture as a Massachusetts cop. Named Billy Costigan, he is tasked to go undercover to infiltrate a group of Irish-American mob, with Frank Costello, played by Jack Nicholson, as their leader gangster. DiCaprio urges the audience to sympathize with him and get worried when he encounters Nicholson as he may slip up. He juggles the dangers of his work undercover because he could get caught and murdered. For his impressive performance, DiCaprio got his fifth Golden Globe Award nomination. Moreover, he was also nominated for his fifth and sixth Screen Actors Guild. This was indeed one of the best Leonardo DiCaprio movies ever.

Blood Diamond 2006

  • Genre: War/Drama
  • Director: Edward Zwick
  • Stars: Leonardo DiCaprio, Djimon Hounsou, Jennifer Connelly
  • Rating: Rotten Tomatoes 63%, IMDb 8

DiCaprio went on to deliver an incredible South African accent when playing his role as Danny Archer. He was a gunrunner who went into jail for smuggling diamonds and was imprisoned with Solmon Vandy, a fisherman portrayed by Djimon Hounsou. And, he was looking for a pink diamond to change their lives. DiCaprio pulled off an impressive performance, for which he got his third nomination for Academy Award, his sixth Golden Globe nod, and his seventh Screen Actors Guild nomination. This is one of the best Leonardo DiCaprio films of all time.

Shutter Island 2010

  • Genre: Thriller/Mystery
  • Director: Martin Scorsese
  • Stars: Leonardo DiCaprio, Mark Ruffalo, Ben Kingsley, Michelle Williams, Patricia Clarkson
  • Rating: Rotten Tomatoes 68%, IMDb 8.2

Shutter Island is another amazing movie in which Leonardo DiCaprio collaborated with Martin Scorsese. This is one of the best Leonardo DiCaprio movies of all time. Moreover, it is considered one of the best performances of DiCaprio’s career. He performs as a US Marshal, Teddy Daniels, investigating a murderer’s disappearance. The woman escaped the criminally insane hospital. While he goes deeper into his operation in the asylum, he realizes he is losing his grasp on reality. There are a lot of disturbing imagery and lingering dread in the movie, but Scorsese was incredible and had DiCaprio lead an earnest performance.

Inception 2010

  • Genre: Thriller/Action/Sci-fi
  • Director: Christopher Nolan
  • Stars: Leonardo DiCaprio, Joseph Gordon, Tom Hardy, Cillian Murphy, Elliot Page
  • Rating: Rotten Tomatoes 87%, IMDb 8.8

The star of Christopher Nolan’s movies is indeed Nolan himself. With an actor like DiCaprio who has a specialty in intricate character work, it is a challenge to perform that in a high-concept sci-fi epic. DiCaprio, however, is able to do his magic as Dom Cobb, who is a thief able to steal secrets by going through their subconscious thoughts. He is then given a chance to redeem himself by accepting the job of implanting an idea into someone’s mind. It is not the deepest performance of DiCaprio but it is still one of the best Leonardo DiCaprio movies of all time.

Read more: Best Drama Movies of All Time

Django Unchained 2012

  • Genre: Western/Drama
  • Director: Quentin Tarantino
  • Stars: Leonardo DiCaprio, Quentin Tarantino, Christoph Waltz, Jamie Foxx, Samuel L. Jackson
  • Rating: Rotten Tomatoes 86%, IMDb 8.4

The next one of Leonardo DiCaprio greatest movie roles is his work in Django Unchained. The 47-year-old had the chance to let the famed Tarantino dialogue just ooze out of his mouth. For his impressive performance as Monsieur Calvin J. Candie, he got his ninth Golden Globe Award nomination. A few years before the Civil War, Jamie Foxx, Django, who is a slave, accompanies an unorthodox German bounty hunter named Dr. King Schultz, trying to capture the Brittle brothers. Then, they accomplish their mission and Schultz sets Django free. Following that, the two start hunting the South’s most-wanted criminals. They then meet the infamous shady Calvin Candie and find out Django’s long-lost wife is yet a slave.

The Wolf of Wall Street 2013

  • Genre: Drama/Comedy
  • Director: Martin Scorsese
  • Stars: Leonardo DiCaprio, Martin Scorsese, Jonah Hill, Margot Robbie, Matthew McConaughe
  • Rating: Rotten Tomatoes 79%, IMDb 8.2

Once again Leonardo DiCaprio worked with Martin Scorsese in the movie the Wolf of Wall Street. Following his impressive performance as Jordan Belfort, the real-life stockbroker, he won his second Golden Globe Award. Belfort’s fraudulent practices helped him gain a fortune but he spent it on sex and drugs. Following a lot of movies in which DiCaprio had interior-based performances, watching him let loose was interesting. This is indeed one of the best Leonardo DiCaprio movies of all time as he got his fourth and fifth Academy Award nomination for Best Actor and producing the Best Picture.

The Great Gatsby 2013

  • Genre: Drama/Romance
  • Director: Baz Luhrmann
  • Stars: Leonardo DiCaprio, Toby Maguire, Carey Mulligan, Joel Edgerton
  • Rating: Rotten Tomatoes 48%, IMDb 7.2

This is an adaptation of F. Scott Fitzgerald’s masterpiece in 1925. DiCaprio plays the role of Jay Gatsby in the movie the Great Gatsby. He earned his wealth in a somehow suspicious way. Moreover, he throws great parties in his mansion on Long Island and he doesn’t even know his guests. He then tells his new friend Nick Carraway the reason behind his actions. So, he admits that he does it with the hope of seeing the woman he loved and lost at the party. Gatsby’s character is quite enigmatic and a true movie star can only pull it off and that is exactly what DiCaprio did. Don’t miss this movie as it is one of the best Leonardo DiCaprio movies of all time.

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The Revenant 2015

  • Genre: Western/Adventure
  • Director: Alejandro González Iñárritu
  • Stars: Leonardo DiCaprio, Tom Hardy, Will Poulter
  • Rating: Rotten Tomatoes 78%, IMDb 8

The Revenant is one of the best Leonardo DiCaprio movies ever and he won his first Academy Award after this role. He also won this third Golden Globe Award and his first Screen Actors Guild Award for playing Hugh Glass in Alejandro G. Iñárritu‘s film. He is left to die by a group of trappers following being mauled by a grizzly bear. Almost like a miracle, Hugh survives and wants to take vengeance on the person who abandoned him. DiCaprio had an enormously physical role and gave Hugh a powerful character with his impressive talent. The movie did deserve to win.

One Upon a Time in Hollywood 2019

  • Genre: Drama/Comedy
  • Director: Quentin Tarantino
  • Stars: Leonardo DiCaprio, Brad Pitt, Margot Robbie, Dakota Fanning, Emile Hirsch
  • Rating: Rotten Tomatoes 85%, IMDb 7.6

One of the best must see Leonardo DiCaprio performances is in the movie Once Upon a Time in Hollywood. DiCaprio plays the role of an actor named Rick Dalton, who comes to fame as the TV Western “Bounty Law” star. However, he along with his stuntman played by Brad Pitt find themselves at a crossroads, where audiences changed their taste and his roles are no longer in fashion. He then becomes a guest on TV shows and begins to search for career salvation. It is then he finds his new neighbor, director Roman Polanski, and his girlfriend Sharon Tate, portrayed by Margot Robbie. DiCaprio shows off his moving performance as a man who should put on a happy face despite knowing that everything might fall apart.

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