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10 Best Leonardo DiCaprio Movies

Updated on September 16, 2014
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This brilliant young actor's career had an auspicious beginning when he was kicked off the set of his first job! Yes, at the tender young age of 5, Leonardo DiCaprio was kicked off the set of Romper Room for being disruptive. However he rebounded nicely with several early TV roles on a series based on the film, Parenthood, drama Santa Barbara and sitcom Growing Pains.

Even at a young age DiCaprio displayed a tremendous acting range in his early films with early roles as a troubled teen addicted to Heroin, an autistic child and a rebellious teenager with an abusive father. He has continued his impressive acting career and is one of the best US actors under 40 years old. At 37, Leo DiCaprio has already been nominated for 3 Academy Awards and likely will be nominated for many more Awards in the future.

In addition to critical acclaim, Leo DiCaprio has also been a success at the box office with several blockbusters, including two films on the all time Top 50 US Box Office films; Titanic and Inception. Leonardo DiCaprio has starred in a variety of genres including action, drama, suspense and horror genres. He has worked with many great Directors, but DiCaprio has worked most often with Martin Scorcese who has cast him as a lead actor in four of his films. That Scorsese has come back to Leo DiCaprio for four films is a testament to his ability as an actor.

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Basketball Diaries movie image leonardo dicaprio
Basketball Diaries movie image leonardo dicaprio

10. Basketball Diaries (1995)

A Cautionary Tale about Teen Drug Abuse

Two years after his amazing role in Gilbert Grape, Leonardo DiCaprio shocked us with another outstanding performance in The Basketball Diaries. Adapted from the book by the same name, the film chronicles the downward spiral of Jim Carroll (Leo DiCaprio), a prep school basketball star who begins to follows a dark path of destruction through rebellion and drug abuse.

A combination of factors including sexual abuse by their prep school Coach, a friend dying of Leukemia, and teenage angst contribute to Carroll's progressive drug use as he follows a dark tunnel down into the abyss -- from high school basketball star to heroin addict and male prostitute. This is not a feel good movie but it is an amazing story and a compelling Leo DiCaprio role that clearly demonstrated his wide range as a young actor.

Much like the 1980s film, Clean and Sober, starring Michael Keaton this is a cautionary tale about the drug abuse and the ease at which problems can escalate for young people caught up with drugs and alcohol.

The film was the first feature film for Director Scott Kalvert but an outstanding Directorial debut. The cast includes Lorraine Bracco (of Soprano's fame) as Jim's mother and Bruno Kirby and Mark Wahlberg as two of Carroll's close friends. It is a gripping and compelling movie and one of my favorite early films featuring Leonardo DiCaprio

Check out this signed Leo DiCaprio photo during the filming of Basketball Diaries.

What's Eating Gilbert Grape movie image Depp Dicaprio
What's Eating Gilbert Grape movie image Depp Dicaprio

9. What's Eating Gilbert Grape (1993)

A Poignant Coming of Age Story in Rural America

What's Eating Gilbert Grape is a critically acclaimed coming of age film set in a small fictional town, Endora. It is a story of a family of kids trying to come to grips with losing their father. Gilbert Grape (Johnny Depp), the oldest of the kids (16 or 17) is not the responsible man of the house and he deals with a lot of responsibility including holding down a job at a convenience store, caring for their morbidly obese mother and looking after his autistic brother, Arnie (Leo DiCaprio).

Gilbert's life is boring, predicable and frankly a burden, until he meets Becky (Juliette Lewis), a new girl in town. Becky is a cute free spirit girl and Gilbert is quickly hooked on her. However, falling in love with Becky is another complication in his already complicated life and he now has to try to juggle this relationship with everything else.

While Depp and Lewis are quite good in this film, it is DiCaprio's performance as the mentally handicapped Arnie is outstanding and he handles the role with poignant compassion. It was not his first feature film role, but Grape was DiCaprio's coming out party with this brilliant performance. DiCaprio was nominated for the Best Supporting Actor Oscar for this role.

If you Liked Gilbert Grape, then Check out Benny and Joon

shutter island movie poster dicaprio scorsese
shutter island movie poster dicaprio scorsese

8. Shutter Island (2010)

An Intense Psychological Thriller Starring Leo DiCaprio

Shutter Island is an intense psychological thriller and the fourth pairing of Martin Scorsese with Leonardo DiCaprio. Set in 1954, US Marshal Teddy Daniels (DiCaprio) is investigating the disappearance of a female murderer who escaped from a mental hospital for the criminally insane on Shutter Island. However, she escaped from a locked room with no sighting by guards. What's more, she disappeared from a facility that is so isolated that no one could live trying to swim to freedom.

As the investigation continues, we discover that there are things going on at Shutter Island facilities that are very disturbing and Daniel's ulterior motive is to stop the atrocities on the island. We discover new facts at every twist and turn of the movie and things are never as they appear. It is a will plot line that takes many twists and turns. You will be captivated throughout and your mind will be working overtime trying to figure out what really is going on between Daniels and the Island team.

Scorsese has assembled an top-notch cast for Shutter Island led by Ben Kingsley and Max von Sydow, the "evil" masterminds at the mental facility. Dicaprio is partnered with Mark Ruffalo as US Marshalls and their interplay is outstanding. It feels as if they have worked together for many years even though they have been thrown together for the investigation. And the real shining star of the films is young Michelle Willams, who plays the ghost of Daniels dead wife, Dolores. She is at times compassionate, at times mysterious and at times outright haunting. A gripping performance for such a young actress, we can expect more good things from Williams.

Gangs of New York movie poster dicaprio diaz day-lewis
Gangs of New York movie poster dicaprio diaz day-lewis

7. Gangs of New York (2002)

A Gangland Epic in NYC's Violent Five Points Neighborhood

Gangs of New York is an epic period film about the Five Points Neighborhood in New York City just prior to the Civil War. Five Points was reputed to be the most dangerous slum in the world at this time and Bill the Butcher (Daniel Day-Lewis) was one of its most notorious gang leaders in the area.

The story follows fictitious character, Amsterdam Vallon (Leonardo DiCaprio), who returns to Five Points after many years away to avenge his father's murder by killing Bill the Butcher many years earlier. Daniel Day-Lewis was outstanding in this film and was nominated for the Best Actor Oscar. The main story is fiction, but it is set against a backdrop of actual events that transpired during 1863 in NYC.

While DiCaprio's role was much demanding than the Bill the Butcher role, he is a thoroughly convincing as a young tough on a mission of revenge. Vallon must first gain Bill's trust to get close enough to kill him. Along the way he falls for one of Bill's girls, Jenny Everdeane (Cameron Diaz). While trying to gain Bill's confidence, Vallon is exposed and he must negotiate his way out of the Devil's lair.

The movie is an entertaining gangland drama that will have you hanging on edge as Bill and Amsterdam seek to kill one other. Ultimately, this movie ends with a classic "all hands" gang fight that denigrates into an all city riot about the newly instituted National Draft for the Civil War.

Titanic movie poster dicaprio winslet
Titanic movie poster dicaprio winslet

6. Titanic (1997)

An Enduring Love Story Set During a Historic Disaster

Titanic was a blockbuster success and is #2 all-time on the movie box office list behind Avatar. With all that success, it has attracted many haters from the movie critic world. However, in reality this was a beautiful epic film about the most famous maritime disaster in history. The sinking of the Titanic is one of those senseless disasters that will remain ingrained in our psyche for hundreds of years. This Leonardo DiCaprio movie uses the sinking as a backdrop to a human drama on the ship, the forbidden love affair of two fictitious characters, Jack Dawson (Leo DiCaprio) and Rose DeWitt Bukater (Kate Winslet), who is engaged to another passenger.

Romantic movies are often panned by critics as sappy and simplistic, but this movie gives us a glimpse into some of the human dramas that must have existed as the ship was sinking. One of the most moving scenes in the movie involves a working class mother singing her children to sleep (as the ship sinks) after abandoning any hope of rescue. It is thought that the crew locked some of the lower class travelers in the lower decks because there were not enough lifeboats on the ship. This gripping scene really brings home the magnitude of the despair of the passengers as the ship was sinking into icy waters.

Unfortunately a side effect of DiCaprio's role in Titanic was that many movie fans and critics viewed him as a simple "pretty boy" actor after this film, without regard to his wide range and critically-acclaimed earlier roles. Those that did were missing out on a tremendous resume of films featuring DiCaprio.

blood diamond movie image dicaprio
blood diamond movie image dicaprio

5. Blood Diamond

A Gripping Tale of an Abused People in Sierra Leone

Blood Diamond is an intense and eye opening film about the diamond trade out of Sierra Leone (Africa). This impoverished country is controlled and dominated large diamond mining companies and the street gangs they use to protect their interests. These gangs and their leaders recruit children and brainwash them into heartless murderers.

Danny Archer (Leonardo DiCaprio) is an opportunistic ex-mercenary gun runner who operates on the border of Sierra Leone. He trades arms for diamonds with the gang leaders but he is caught on the border trying to smuggle the diamonds into nearby Liberia and is thrown into prison. While in prison, he overhears a story about a very large diamond that was recently discovered in Sierre Leone from another inmate, Soloman Vandy (Djimon Hounsou). Vandy was captured after his family was captured in the region but he knows where the diamond is hidden. Archer arranges to have Vandy released and the two pair up to recover the diamond and rescue Vandy's family.

While the film is partly an action thriller, it is really a chilling drama that sheds light on the atrocities being committed by these local gangs in Western Africa. The most harrowing scenes involve the brainwashing methods used by the gangs on young boys. It will absolutely leave an lasting impression.

There are so many compelling performances in this film that I cannot name them all. The film was nominated for five Academy Awards including Best Actor (DiCaprio) and Best Supporting Actor (Hounsou). This film is truly a must see film for everyone to expose these brutal atrocities to more of the world.

If you liked Blood Diamond, you should check out The Last King of Scotland

Inception movie image leonardo dicaprio
Inception movie image leonardo dicaprio

4. Inception (2010)

Leo DiCaprio's Fastest Paced Action Thriller yet

Inception became an instant sci-fi and cult classic when released in 2010. It's highly complex plot and futuristic "dream invasion" themes were well received by techies and science fiction fans. What's more the film was written and directed by Christopher Nolan who has already developed a cult following among fans despite being 41 and only completing nine films to date.

Cobb (Leo DiCaprio) is a skilled dream thief with a checkered past. Cobb steals valuable secrets from business executives and others during their dreams using technology that allows him to become a character in another person's dreams. As the story unfolds we learn that there are actually four levels of dream state and it requires an increasing amount of skill, and produces much more risk, to penetrate into deeper levels. We also learn that Cobb is one of the few people that has ever penetrated into the fourth level of a dream state and something bad happened when he last did so. And yet, in order to complete a huge life altering heist, Cobb and his team must negotiate the risks of penetrating into the fourth level of a Japanese business leaders dreams.

Cobb's mentor, Miles (Michael Caine), knows about Cobb's past and advises him against taking this job, but when Cobb refuses to quit Miles decides to help assemble the team to protect him as much as possible. The team is played by a group of talented young actors including Joseph Gordon-Levitt, Ellen Page, Tom Hardy, Ken Watanabe and Lukas Haas.

While not his most challenging role, DiCaprio is able to balance toughness and vulnerability while leading the team and fighting his own past demons. As usual, Christopher Nolan has excelled at putting together a unique film that stuns us both mentally and visually. Inception was nominated for 8 Academy Awards, including Best Picture and Best Original Screenplay. It wone 4 Oscars, including Best Cinematography and Best Visual Effects.

I cannot explain too much of this movie without spoiling valuable portions of the film, but this Leo DiCaprio film is excellent and highly entertaining. It is a non-stop action adventure with a highly unique sci-fi premise.

The Aviator movie image dicaprio airplane
The Aviator movie image dicaprio airplane

3. The Aviator (2004)

An Epic Biopic on Howard Hughes

The Aviator is a biopic film about Howard Hughes (Leonardo DiCaprio), the legendary film director and aviation industry magnate. The movie follows Hughes early years during the 30s and 40s and the beginnings of his germ phobias. While no one knows for sure what caused Hughes germ phobias late in life but the film postulates that it stemmed from his mother's obsessions with bathing and cleaning during early polio epidemics.

Howard Hughes was a fascinating man who led a very interesting life. After taking over his father's regional Hughes Tool Co., he led a major expansion effort primarily into the aircraft industry which fit with is passion for flying. During his early career, Hughes dramatically grows the company and eventually moves the headquarter to Los Angeles. In LA, Hughes becomes obsessed with the film industry and makes several feature films including the war epic, Hell's Angel. During this period of his life he is reputed to have dated Katherine Hepburn (Cate Blanchett), Ava Gardner (Kate Beckinsdale) and Jean Harlow (Gwen Stefani).

The Aviator is one of four films that Martin Scorsese directed while pairing with Leonardo DiCaprio. They combine brilliantly to build one of the most robust characters depicted on film. Leonardo portrays a highly complex Hughes from relationships with several Hollywood starlets to his obsessive personality regarding both germs and perfection. You feel compassion for the character while also being repulsed by his crazy behavior. It is an engrossing story that provides a glimpse into both early Hollywood and Howard Hughes' life.

Catch Me If You Can movie image dicaprio
Catch Me If You Can movie image dicaprio

2. Catch Me If You Can (2002)

A Crime Suspense Thriller based on an Unbelievable True Story

Catch Me If You Can is the true story of Frank Abagnale, Jr (Leo DiCaprio) who conned his way through an astonishing number of careers (and paychecks) including, airline pilot, doctor, legal prosecutor and history professor. Frank Jr is particularly tormented by his parents divorce and in particular the shell of a man his father (Christopher Walken) becomes after his mother (Nathalie Baye) cheats on him and leaves him for another man. This torment leads Frank Jr. to create his own fraudulent, alternative world by using his ability to charm people that he learned from his salesman father.

The film chronicles the real life chase by FBI Agent Carl Hanratty (Tom Hanks) to track down and arrest Frank, Jr. This cat and mouse manhunt is fascinating and while Hanratty is always close on his trail, Frank, Jr. is able to allude him for years. One of the most fascinating scenes is a hotel room scene in which Frank, Jr. actually cons Hanratty while investigating a crime that occurred just minutes before.

The film is directed by Steven Spielberg who once again wields his cinematic genius to create this outstanding drama thriller. The entire cast is outstanding but Hanks and DiCaprio are the true keys in this film. Leonardo shows us a vulnerable side and we actually find ourselved rooting for him to escape despite being a major con artist. He is so convincing in the role that I found myself looking forward to the next bit of charm he is going to use in his next con.

In a surprise, Catch me if you Can was only nominated for two Academy Awards, including Best Supporting Actor (Walken) and Best Original Score. However, it is a fantastic movie that will stand the test of time as a future classic.

If you liked Catch Me if you Can, then you might also like Blow

The Departed movie poster dicaprio damon nicholson
The Departed movie poster dicaprio damon nicholson

1. The Departed (2006)

A Scorcese Masterpiece and One of the Best Gangland Thrillers

The Departed is one of my favorite gangster movies and a captivating story about undercover and double agents. Set in Boston, this Martin Scorsese film is a story of police corruption and Irish gangs that run the city. The amazing cast includes Leonardo DiCaprio, Jack Nicholson, Matt Damon, Mark Wahlberg, Martin Sheen and Alec Baldwin.

Billy Costigan (DiCaprio) is an undercover cop assigned to infiltrate the Irish mob led by Frank Costello (Nicholson). At the same time, Costello has sent one of his young up and comers, Colin Sullivan (Damon), to infiltrate the police force as a mole. As the story unfolds these two men are pitted against each other both on the surface and again at the "double cross" level. This complex story takes many twists and turns and the ending will surely surprise you.

The cast is so excellent that no one actor stands out above the others. However, Leo DiCaprio is excellent in his role as an up and coming mobster who becomes one of Costello's trusted lieutenant, of course all the while, he is actually an undercover police agent trying to avoid being revealed.

The Departed was nominated for five Academy Awards and won four Oscars, including Best Picture, Best Director (Scorsese) and Best Adapted Screenplay. This film is great on so many levels that it will definitely live on as one of the greatest gangster films of all time.

If you liked The Departed, then you should also watch Mystic River

Vote for Your Favorite Dicaprio Movie

Which is the Best Leonardo DiCaprio Film (including some not on list).

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What did you think about this DiCaprio lens?

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    • profile image

      Niktravelfit 3 years ago

      Nice lens. Too bad he did not get an Oscar yet - he really deserves it.

    • NibsyNell profile image

      NibsyNell 4 years ago

      Just seen him in The Great Gatsby and he blew me away! Gonna check out more of his films now.

    • profile image

      anonymous 4 years ago

      Great lens, Basketball diaries is a great film

    • profile image

      anonymous 4 years ago

      Well...I am in LOOOOOVE with him! It was hard to pick my favorite movie...Blood Diamond made me never want to purchase or own a real diamond ever again...

      Catch me if you can...I loved...The Departed...and, and, and.....

    • Underrated profile image

      Underrated 4 years ago

      He needs to get an Oscar finally. We all know he deserves it.

    • notsuperstitious1 profile image

      Edith Rose 4 years ago from Canada

      I love DiCaprio Movies. Thank you for liking my lens

    • notsuperstitious1 profile image

      Edith Rose 4 years ago from Canada

      I love DiCaprio Movies. Thank you for liking my lens

    • profile image

      Aunt-Mollie 4 years ago

      He really is an excellent actor.

    • profile image

      pinoyrecipe 4 years ago

      cool, dicaprio gain fame from his movie titanic

    • profile image

      achivevery 4 years ago

      dicarpio ----->>> titanic

    • profile image

      MarcellaCarlton 4 years ago

      I love, love this lens! He is a great actor and very entertaining to watch no matter what the film.

    • Ashly Rain profile image

      Ashly Rain 4 years ago

      Great lens. I loved The Basketball Diaries.

    • profile image

      anonymous 4 years ago

      He reminds me of someone that i love him too much.he is a different actor.i love him.

    • profile image

      anonymous 4 years ago

      He reminds me of someone that i love him too much.he is a different actor.i love him.

    • WriterJanis2 profile image

      WriterJanis2 4 years ago

      What a great actor he is.

    • maryLuu profile image

      maryLuu 4 years ago

      Nice selection! But my favorite movie with DiCaprio remains "The Beach"!

    • Valentina65 profile image

      Valentina65 4 years ago

      I am a huge Leo diCaprio fan - I even met him in Rome at a film premiere!

    • Deborah Swain profile image

      Deborah Swain 4 years ago from Rome, Italy

      Excellent lens...when will the Academy finally give Leo the Oscar he deserves I wonder?!

    • TolovajWordsmith profile image

      Tolovaj Publishing House 5 years ago from Ljubljana

      Great lens about important actor. I believe he was a bit unlucky to act in titanic so young. It determined him and he needed years to get the role where he could show his acting potential in full.

    • profile image

      anonymous 5 years ago

      I like it.

    • profile image

      anonymous 5 years ago

      DiCaprio is one of the best movers and shakers - without a doubt! :))

    • profile image

      AnnaleeBlysse 5 years ago

      This is not the "chick flick" version. LOL. I forgot how young he was in What's Eating Gilbert Grape. I saw the movie in theaters when it was released, but not since.

    • harty5680 profile image

      harty5680 5 years ago

      I would've liked to see Revolutionary Road up there but I'm not sure which one to take down. And J. Edgar...can't wait to see that one.

    • youthministry profile image

      Paul Turner 5 years ago from Birmingham, Al.

      You don't realize it, but Leo has quite a body of work. He climbed quietly with good role choices.

    • lauralie lm profile image

      lauralie lm 5 years ago

      The Departed was great, but really enjoyed DiCaprio's performance in What's Eating Gilbert Grape.

    • profile image

      healthandsick 5 years ago

      departed and inception are great movies with him

    • profile image

      Shadrosky 5 years ago

      The Departed all the way!

    • sousababy profile image

      sousababy 5 years ago

      I haven't seen all of these movies, but his acting was incredible in 'What's eating Gilbert Grape.' When I heard he was the lead in Titanic, I had a hard time (at first) envisioning him as a leading man . . but he can do it all. I haven't seen Inception (yet) but according to your lenses, I guess I had better.

    • ajgodinho profile image

      Anthony Godinho 6 years ago from Ontario, Canada

      I love Leo's movies 'cos he's an amazing actor and I've seen many of his movies. Great selection here!

    • profile image

      anonymous 6 years ago

      @anonymous: Yes Tipi, I forgot about that Movie and you are right; I too was impressed!

    • profile image

      anonymous 6 years ago

      Inception made #3, I figured that one was #1?!? Well it is in my book, I liked that movie and I thought Leo played that part well! :)

      I knew Titanic had to make the list, that's another one of my Favorites!! This was another hard Poll to make a Choice, but I choose "Inception" over "Titanic"; it wasn't easy!

    • profile image

      anonymous 6 years ago

      Leonardo DeCaprio is and amazing actor and very adaptive to a variety of roles. I was particularly impressed with his character in The Gangs of New York.

    • JublyJem profile image

      JublyJem 6 years ago

      it had to be titanic. He was just gorgeous in it! great lens :)

    • akumar46 lm profile image

      akumar46 lm 6 years ago

      Titanic is my favorite romantic tragedy film.

    • Krafick profile image

      Krafick 6 years ago

      The Departed is my favorite. Rafick

    • Rankography profile image
      Author

      Rankography 6 years ago

      @howtocurecancer: It's a great film. Definitely add it to your Netflix queue.

    • howtocurecancer profile image

      howtocurecancer 6 years ago

      I never knew about What's Eating Gilbert Grape, great lens.

    • TonyPayne profile image

      Tony Payne 6 years ago from Southampton, UK

      Leonardo has some great movies, he just keeps getting better. Lensrolled and added to my Leonardo DiCaprio Movies and Collectibles lens.