Top 10 Leonardo DiCaprio Movies of All Time

Updated on December 6, 2019
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Ma-re is an art lover who appreciates beauty in entertainment.

We all love Leo for his promising performances. Whether he is a bad boy, a romantic boyfriend, or a mentally disabled child, we can'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 movie roles of all time.

Ten Best Leonardo DiCaprio Films

  1. Titanic
  2. What's Eating Gilbert Grape
  3. Romeo + Juliet
  4. Catch Me If You Can
  5. The Departed
  6. Django Unchained
  7. The Basketball Diaries
  8. The Aviator
  9. Revolutionary Road
  10. The Man in the Iron Mask

1. Titanic

Leo's most popular movie performance of all time is playing Jack Dawson in the award-winning 1997 movie Titanic. This record-breaking movie that stunned millions across the globe created a cultural phenomenon. Besides the heartbreaking story of the tragic ship, there's also Leo and Kate's chemistry that captivates the audience. There is no doubt that this film set the bar for Leo's career. It's one of the greatest 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. They did this when there was only a 165-page outline James Cameron had written.
  • The hands seen sketching Rose are not DiCaprio's but rather director James Cameron's. In post-production, Cameron, who is left-handed, reversed 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 in at number four in The 100 Greatest Movie Lines by Premiere in 2007. The same line 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 he turned it down. He considers this to be a big regret.

2. What's Eating Gilbert Grape

In this emotional, tearjerking movie, our young Leo plays Arnie Grape, who is a mentally disable 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 that it brought him his first Oscar nomination. 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 has said that playing Arnie Grape was "the most fun I've ever had."
  • When getting into character, Leo remarked, "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 of 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 was already a heartthrob for being the handsome, sexy, and romantic boyfriend that every single lady dreamed of having. He's played Romeo in the 1996 adaptation of Shakespeare's most popular tragic play, Romeo + Juliet. Set in the modern era, Baz Luhrmann's adaption takes the classic play and gives it a histrionic tone with the backdrop of a gang war. Although Kate and Leo's chemistry is so perfect in Titanic, it is undeniable that Leo and Claire are also stunning here.

Fun facts:

  • DiCaprio's delivery of Romeo's speech at the end was so good that it moved Claire 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!"
  • Danes' first day on set filming with 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.
  • Danes and DiCaprio initially did not get along well on set. Danes accused 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 could be a fugitive? Leo is one in Steven Spielberg's hit movie Catch Me if You Can. Leo is Frank Abagnale, a real-life conman who traveled around the country and lived the high life as he impersonated pilots, lawyers, and doctors. The movie follows Frank as he transforms from a fresh-faced teenager into a romantic, brooding young man. Leo's acting from one disguise to another is just so convincing that it feels like he's not just impersonating.

Fun facts:

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

5. The Departed

One of the most intense roles that Leo has 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 and fascinating tale of competing cat-and-mouse games. Seeing Leo's performance here is very intense. He appears very unglamorous as a desperate man who almost loses his identity. This is one of his all-time great 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 Warner Bros. Studios initially did not want to favor him over his co-stars. As such, he was not placed in the leading actor category. The studio favored his leading performance in Blood Diamond (which eventually got him a nomination). DiCaprio himself refused to campaign against his male co-stars in the supporting actor category, so Warner did not campaign for him in this category.
  • Leo was cast in the title role in The Good Shepherd (2006), but he dropped out to play Billy Costigan in this movie.
  • DiCaprio described his one-on-one scene with Jack Nicholson as "one of the most memorable moments of my life."

6. Django Unchained

Playing the role of 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 in Quentin Tarantino's hit movie Django Unchained created a memorable role where he was the bad guy playing his cards in a sophisticated manner. Candie is a man who forces his slaves to fight each other, has a weird fascination with France, and is, at heart, a murderous psychopath.

Fun facts:

  • When DiCaprio's character 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 by this that he used this take in the final print. 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, Leo 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."
  • 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, 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

This is another film with a young Leo, and this film is proof that Leo was born to act. His role in the adaptation of Jim Carroll's memoir, The Basketball Diaries, is a big shift from playing the sweet, innocent, and mentally disabled Arnie in What's Eating Gilbert Grape. Leo plays a high school basketball star who eventually becomes a broken and homeless drug addict. Leo's performance brought a dramatic atmosphere to the portrayal of the struggles of a broken teenager.

Fun facts:

  • The guy Jim talks to in the underground drug den is the real Jim Carroll.
  • DiCaprio and Juliette Lewis previously appeared together in What's Eating Gilbert Grape (1993).
  • This is the first film with DiCaprio and Mark Wahlberg. They would later appear together in The Departed.
  • Jim Carroll was unaware of who Leo 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, Leo hung out in Greenwich Village and went to a poetry reading with Carroll.

8. The Aviator

This movie is another one from Martin Scorsese. Leo plays the role of Howard Hughes in his early years of being an inventor and a big time millionaire businessman. He's facing a lot of problems in almost every facet of his life. As he tries to continue chasing his plans and dreams, there are times when he's about to snap. Leo's portrayal of this part of Howard's life is truly convincing. He's definitely a great actor in this movie.

Fun facts:

  • Leo 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 the actual home he lived in on Muirland Drive.
  • The real Howard Hughes was still married to Ella Botts Rice during the production of Hell's Angels (1930). He would have been balancing his love life between Evelyn Brent and Billie Dove.
  • DiCaprio received an Oscar nomination for playing Howard Hughes.
  • DiCaprio (standing roughly 6'0") is several inches smaller than the actual Howard Hughes (who was 6'4").

9. Revolutionary Road

This 2008 movie is special as Leo and his Titanic partner Kate Winslet were reunited for this adaptation of Richard Yates' classic novel, Revolutionary Road. This movie is mainly about suburban despair and two adults who realize that life is not as easy as as they would like. Contrary to their adventurous and colorful characters in Titanic, their roles in this movie is more grounded and full of problems. Leo's excellent performance in this movie is his signature freakout scene, where we're all stunned and scared for a moment as he bursts out in anger and disappointment.

Fun facts:

  • While directing the love scene between Leo and Kate, director Sam Mendes (husband of Winslet at the time) opted to watch the monitor from another room.
  • This was the second movie DiCaprio and Winslet worked on together since Titanic. Paramount Pictures, which distributed Titanic in the U.S., was the worldwide distributor for this film.
  • This film marked the second time Kate Winslet had 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.

10. The Man in the Iron Mask

This film came after the success of Titanic. Leo plays the sneering playboy King Louis XIV as well as his long-imprisoned twin brother, Philippe. Young Leo shows his versatility here as he was able to play two different characters in one movie!

Fun facts:

  • 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 of Duc d'Orleans.
  • MGM discovered that the audience the movie attracted was directly related to appeal of Leonardo DiCaprio, which was roughly 55% female and 46% under the age of 25.
  • The film cast includes two Oscar winners in Leonardo DiCaprio and Jeremy Irons. It also includes two Oscar nominees in John Malkovich and Gérard Depardieu.

What Is Your Favorite Leonardo DiCaprio Movie?

See results

© 2016 Mare-sensei


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    • profile image


      4 weeks ago

      I agree with everything, all of his movies are amazing plus the fact that he is an amazing actor but they should have put shutter island in there because that movie was amazing and the twist in the end was just surprisingly amazing plus I he fact that his acting in that movie was fenomenal

    • profile image


      5 weeks ago

      If Leonardo DiCaprio hit me with a bus, I would say "thank you" :)

    • profile image


      5 weeks ago

      Where is Inception and the great Gatsby ?

    • profile image


      11 months ago

      wolf of wallstreet

    • profile image


      14 months ago

      Leonardo diCarpio

    • profile image

      Allesca Pakhrin 

      15 months ago

      I love Leonardo dicapricon

    • poppyr profile image


      19 months ago from Enoshima, 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.

    • profile image


      21 months ago

      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


      21 months ago

      I love your Romeo and Juliet and it's great

    • profile image

      salman khan 

      2 years ago

      I love Leonardo dicaprio

    • profile image


      2 years ago

      I just love this guy....

      Ebiraland Media.

    • profile image

      tamanna ganguly 

      2 years 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


      3 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 

      3 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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