Top 10 Greatest Leonardo DiCaprio Movies of All Time

Updated on February 17, 2019

We all love Leo for his promising performance. May he be a bad boy, a romantic boyfriend, or a mentally-ill child, we couldn't deny the fact that he's an incredible actor. Plus, he's the King of Freak-Out scenes! Now, let's find out his top 10 greatest movie roles of all time.

1. Titanic

His most popular movie performance of all is playing Jack Dawson in the award-winning 1997 movie, Titanic. This box-office, record-breaking movie that stunned millions of people across the globe has made a worldwide phenomenon that goes deep down in history. Besides the heart-breaking story of the tragic ship, there's also Leo and Kate's chemistry that binds the audiences into a more level of attachment. No doubt, it's still the summit of Leo's career, and one of the greatest old-school movies to come out of Hollywood in the last 20 years.

Fun facts:

  • Leonardo DiCaprio and Kate Winslet committed to the film even before the script was written, on the basis only of a 165-page outline James Cameron had written.
  • The hands seen sketching Rose are not Leonardo DiCaprio's, but director James Cameron's. In post-production, Cameron, who is left-handed, mirror-imaged the sketching shots so the artist would appear to be right-handed, like DiCaprio.
  • The movie's line "I'm the king of the world!", which was ad-libbed by Leonardo DiCaprio, was voted as the #4 of "The 100 Greatest Movie Lines" by Premiere in 2007. The same was voted as the #100 movie quote by the American Film Institute (out of 100).
  • Both Kate Winslet and Leonardo DiCaprio learned how to dance the polka for the scenes set at the party in the third-class compartments.
  • Johnny Depp was offered the role of Jack Dawson, but turned it down, and considers it a big regret.

2. What's Eating Gilbert Grape


In this emotional, tear-jerking movie, our young Leo plays Arnie Grape, who is a mentally handicapped teenager. He's the younger brother of Gilbert (Johnny Depp), who struggles to bring their family out of difficult circumstances. Leo's performance as a mentally disabled teen is so convincing, it'll make you think that he's definitely not normal at all. This movie brought our young Leo to his first Oscar-nominated role. It's just so sad that he won't be able to tell his "Mamma" about his Oscar award, because she won't wake up anymore.

Fun facts:

  • Leo said that playing Arnie Grape was "the most fun I've ever had."
  • When getting into character, Leo remarked of it, "I had to really research to get into the mind of somebody like that. I spent a few days at a home for mentally retarded teens. We just talked and I watched their mannerisms. People have these expectations that mentally retarded children are really crazy, but that isn't so. It's refreshing to see them because everything's so new to them."
  • Leo created Arnie's trademark flicking his finger against his nose, describing it as a sort of "brain Arnie is massaging the inside of his brain."
  • Leo really did not bathe during the period in filming when Arnie refused to go near water!
  • Leo played Arnie Grape's character so well that when he showed up for the film's premiere, many people were shocked and astonished to learn that the young actor was not actually mentally disabled.

3. Romeo + Juliet

Before Leo had the role of Jack in Titanic, he's already a hot icon for being the handsome, sexy, and romantic boyfriend that every single ladies dream of having. He's played Romeo in the 1996 movie adaptation of Shakespeare's most popular tragic play, Romeo + Juliet. Set in the modern era, Baz Luhrmann's histrionic, gang-war-filled setting take on the classic play. Although Kate and Leo's chemistry is so much perfect in Titanic, it is undeniably true that Leo and Claire's pair up is also stunning.

Fun facts:

  • Leonardo DiCaprio's version of Romeo's speech at Juliet's bier was so good it movedClaire Danes to tears, nearly ruining the scene. The moment the director yelled "cut!," Danes smacked DiCaprio on the arm and said, "Don't make me cry. I'm supposed to be comatose, here!"
  • Claire Danes's first day on set filming with Leonardo DiCaprio was the topless scene after Romeo and Juliet have first spent the night together.
  • Leonardo DiCaprio was Baz Luhrmann's first choice to play Romeo.
  • Claire Danes and Leonardo DiCaprio initially did not get along well on set. Danes accused Leonardo DiCaprio of being immature, while Leo said Danes was just uptight.

4. Catch Me If You Can


Who would've thought that this handsome, good-looking man is a fugitive? Not in real life though, but in Steven Spielberg's hit movie, "Catch Me if You Can". Leo is Frank Abagnale, a real-life con-man who traveled around the country and lived the high life as he impersonated pilots, lawyers, and doctors. The movie develops as Frank transforms from a fresh-faced teenager into a romantic, brooding young man until he's become a totally different person. Leo's acting from one character to another is just so promising, we'll all convinced that he's not just impersonating.

Fun facts:

  • To get her to achieve the way he wanted her to sloppily kiss Leonardo DiCaprio, Steven Spielberg asked Amy Adams to pretend she was starving to death and eating a cheeseburger.
  • According to the real Frank Abagnale Jr. approximately 80 percent of the movie is true.
  • Until he saw the results of Leonardo DiCaprio's work, the real Frank Abagnale Jr. didn't think DiCaprio was "suave" enough to play him.
  • When Frank begins recruiting decoy flight attendants; when announcing the girls picked he announces the actresses by real name.
  • 17-year-old Frank tells Brenda he's 28 years old, which was Leonardo DiCaprio's true age when Catch Me If You Can premiered in 2002.

5. The Departed


One of the most intense roles that Leo ever had was playing the role of Billy Costigan as a cop infiltrating the mob. Together with Matt Damon as a mobster infiltrating the police force, the film is an intricate, fascinating tale of competing cat-and-mouse games. However, the film director and his screenwriter infuse it with so much tragedy that it winds up becoming something almost mythic. But seeing Leo's performance is just so intense, in a totally unglamorous way by being a desperate man who almost loses his identity. It's one of his all-time greatest performances.

Fun facts:

  • Leo could've won an Oscar award for this movie. A possible reason why he did not receive an Oscar nomination for his performance in this movie was because the Warner Bros. Studios initially did not want to favor him over his co-stars and place him in the leading actor category. The studio favored his leading performance in Blood Diamond (2006) (which eventually got him a nomination). DiCaprio himself refused to campaign against his male co-stars in the supporting actor category, so Warner bought no supporting actor ads for DiCaprio, and he did not receive a nomination.
  • Leonardo DiCaprio was cast in the title role in The Good Shepherd (2006), but he dropped out to play Billy Costigan in this movie.
  • Leonardo DiCaprio called his one-on-one scene with Jack Nicholson "one of the most memorable moments of my life."

6. Django Unchained


Playing the matured role of a slave owner Calvin Candie in a smooth and attractive way is definitely a credit to Leo's amazing talent. His dirty, racist, and demented heart on Quentin Tarantino's hit movie "Django Unchained" brought him into a remarkable role of being the bad guy playing his cards on a sophisticated way. This is a man who breeds and forces his slaves to fight each other, who has a weird fascination with France, and who is, at heart, a murderous psychotic.

Fun facts:

  • When Leonardo DiCaprio's character Calvin Candie smashes his hand on the dinner table, the actor accidentally crushed a small stemmed glass with his palm and really began to bleed. DiCaprio ignored it, stayed in character, and continued with the scene. Tarantino was so impressed that he used this take in the final print, and when he called cut, the room erupted in a standing ovation. DiCaprio's hand was bandaged and he suggested the idea of smearing blood onto the face of Kerry Washington. Tarantino and Washington both liked this, so Tarantino got some fake blood together.
  • During the filming of one of the dinner scenes, Leonardo DiCaprio had to stop the scene because he was having "a difficult time" using so many racial slurs. Samuel L. Jackson then pulled him aside telling him, "Motherfucker, this is just another Tuesday for us."
  • Leonardo DiCaprio, whose role marked the first time he played a villain since The Man in the Iron Mask (1998), was uncomfortable with how horrible and explicitly racist his character was. However, Quentin Tarantino convinced him to be as menacing as possible, saying that if he didn't take it all the way, people would hold it against him forever.

7. The Basketball Diaries


Another young Leo movie, this is just one of the many proofs that Leo was born to act. His role in the movie adaptation of Jim Carroll's memoir, The Basketball Diaries, is a big shift from playing the sweet, innocent, and mentally-challenged Arnie in "What's Eating Gilbert Grape" to a high school basketball star, who eventually becomes broken, and worse, a homeless drug addict. But Leo's flexible character made him so amazing in this movie, which brought a dramatic atmosphere in his struggles as a broken teenager.

Fun facts:

  • The guy Jim talks to in the underground drugden, is the real Jim Carroll.
  • Leonardo DiCaprio and Juliette Lewis previously appeared together in What's Eating Gilbert Grape (1993).
  • This is the first film with Leonardo DiCaprio and Mark Wahlberg. They would later appear together in The Departed.
  • Jim Carroll was unaware of who Leonardo DiCaprio was at first. "When they first told me it was gonna be Leo, I didn't know who he was," Carroll told The Los Angeles Times. "If they'd said the kid from Growing Pains (1985), I would have known, because when I first saw that kid, I said, 'This kid has a lot of presence.' I said, 'That kid is very pretty. He's gonna do well.'"
  • To prepare for his role, Leonardo DiCaprio hung out in Greenwich Village and went to a poetry reading with Carroll.

8. The Aviator


This movie is another Martin Scorsese's. Leo plays the role of Howard Hughes in his early years of being an inventor, and at the same time, a bigtime millionaire businessman. He's facing a lot of problems in almost everything. As he tries to continue chasing his plans and dreams, there are times when he's about to get mad, and Leo's characterization on this part of Howard's life is truly convincing. He's definitely a great actor for this movie.

Fun facts:

  • Leonardo DiCaprio spent a day with Jane Russell to hear her memories and impressions of Howard Hughes. She was very impressed with DiCaprio's visit and told him that Hughes was a quiet yet extremely stubborn man who always got his way in the end.
  • Howard Hughes' Los Angeles home in the film was actually the home he lived on Muirland Drive.
  • The real Howard Hughes was still married to Ella Botts Rice during the production of Hell's Angels (1930) and would have been balancing romantic involvement with Evelyn Brent and Billie Dove.
  • Leonardo DiCaprio received an Oscar nomination for playing Howard Hughes.
  • Leonardo DiCaprio (standing roughly 6ft) is several inches smaller than the actual Howard Hughes (6ft4).

9. Revolutionary Road

This 2008 movie is kind of special, as Leo and his Titanic partner Kate were reunited for this adaptation of Richard Yates' classic novel "Revolutionary Road". This movie is mainly about suburban despair and two adults who realizes that life is not as easy as one-two-three. Contrary to their adventurous and colorful characters in Titanic, their roles in this movie is matured and somehow full of problems. Leo's excellent performance in this movie is his signature freak-out, where we're all stunned and scared for a moment as he burst out his anger and disappointment.

Fun facts:

  • While directing the love scene between Leonardo DiCaprio and Kate Winslet, director Sam Mendes (husband of Winslet at the time) opted to watch the monitor from another room.
  • This was the second movie Leonardo DiCaprio and Kate Winslet worked on together since Titanic (1997). Paramount Pictures, which distributed the early film in the U.S., was the worldwide distributor of this film.
  • This film marked the second time Kate Winslet has been in a movie where she makes love in a vintage car, and someone's hand hits the window and slides down it in the throes of passion. The first time was in Titanic (1997).

10. The Man in the Iron Mask


After the success of Titanic comes this movie. Leo, who played the sneering, playboy King Louis XIV with his long-imprisoned twin has become a hit after Leo's stardom in Titanic. Young Leo was so versatile, he was able to play two different characters in one movie! Besides, we can also see Leo in his elegant robes while hiding the fact that there's something more dreadful in those shiny dress.

Fun facts:

  • Leonardo DiCaprio's mask was made out of polystyrene.
  • Louis XIV did have a brother named Philippe, but he was not a twin. He was several years younger, a flamboyant homosexual, and had the title Duc d'Orleans.
  • MGM discovered the audience the movie attracted was "directly related to appeal of Leonardo DiCaprio", being 55% female and 46% under the age of 25.
  • The film cast includes two Oscar winners: Leonardo DiCaprio and Jeremy Irons; and two Oscar nominees: John Malkovich and Gérard Depardieu.

What is your favorite Leonardo DiCaprio movie?

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Questions & Answers

    © 2016 Mare-sensei


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      • profile image


        4 weeks ago

        Leonardo diCarpio

      • profile image

        Allesca Pakhrin 

        6 weeks ago

        I love Leonardo dicapricon

      • poppyr profile image


        6 months ago from Tokyo, Japan

        This is a great article. Leonardo Dicaprio is a wonderfully talented and diverse actor. I agree he was amazing in Django Unchained but I'll always have a soft spot for Titanic. I loved the interesting facts you included in this artice; I never knew Johnny Depp was considered for the part of Jack! I bet he would have been great as well. It's hard to say whether he actually would have been the better choice, though.

      • PoetikalyAnointed profile image


        7 months ago from US

        Nice list and wonderful actor.

        I've never heard of/seen The Basketball Diaries or Revoluntionary Road. I'll have to prep those out.

        My fav is Titanic-hands down!

      • profile image


        8 months ago

        I love your Romeo and Juliet and it's great

      • profile image

        salman khan 

        11 months ago

        I love Leonardo dicaprio

      • profile image


        11 months ago

        I just love this guy....

        Ebiraland Media.

      • profile image

        tamanna ganguly 

        14 months ago

        Leonardo DiCaprio IJUST LOVVVVVVVVVE YOU AND PLEASE i want to see you in the role of spiderman.....plEEEEEAAAse...............and i love Jack Dawson ............and TITANIC toooooooooooooooo

      • profile image


        2 years ago

        Leo's arnie grape is my favorite. I really thought he's mentally ill. Superb acting at such a young age!

      • Sunshine625 profile image

        Linda Bilyeu 

        2 years ago from Orlando, FL

        I didn't know that Johnny Depp was offered the role as Jack Dawson!! I also regret he turned down the offer.


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