Best Leo DiCaprio Movies

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

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If you found Basketball Diaries compelling, you should also see Requiem for a Dream. A gripping tale of addiction whether it is heroin, food or cable shopping. This film will grab you and shake you from the opening credits right through the bitter end.

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.

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If you loved What's Eating Gilbert Grape, then do yourself a favor and see Benny and Joon. In one of Johnny Depp's best acting performances, Benny and Joon is a beautiful coming of age story between a strange, but entertaining Benny and the mentally challenged Joon.

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 noone 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.

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If you enjoyed Shutter Island, then you should also like the action thriller, Body of Lies. This intense spy thriller is set in the Middle East and features Leonardo DiCaprio as the field agent and Russell Crowe as his Washington "handler".

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.

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If you liked Gangs of New York, then you are likely to enjoy Once Upon a Time in America. Another great historical fiction about gangs in New York City. This film is set during Prohibition and follows a Jewish gangs rise to prominence as bootleggers.

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.

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If you loved Titanic, then you might also enjoy A Walk in the Clouds. This film is a forbidden love story in which a man helps out a woman in distress but then assumes a different persona to continue to help here without revealing a deep secret he has.

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.

Buy this limited edition original movie poster from this gripping Di Caprio film or buy this collectible autographed photo of DiCaprio during filming of Blood Diamond.

If you were captivated by this gripping tale, you may also want to see The Last King of Scotland. This is a disturbing true account of Nicholas Garrigan (James McAvoy) who gets caught up in Uganda during Idi Amin's rule. After a chance meeting with the ruler, Amin takes a like to Garrigan and he becomes a trusted advisor. However, he slowly learns that Amin is absolutely crazy and a brutal dictator and looks for a way to escape the country.

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.

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If you were captivated by The Aviator, you should also see Hughes most famous film, Hells Angels. This classic 1930's film directed by Howard Hughes starred Jean Harlow and Ben Lyon. During filming, Hughes was so obsessed with perfection for the air battles that he often waited for the perfect cloud formations for filming.

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.

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If you loved the non-stop sci fi action of Inception, you should also check out Minority Report. Starring Tom Cruise and set 50 years in the future, the police are able to stop most crimes before they happen using a very strong neural computer network. However, when one such officer is falsely accused of a crime he was not going to commit, he sets out to prove his innocence.

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 occured 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.

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If the Catch Me if You Can was right up your alley, you should also check out Johnny Depp's Blow. This real life biopic is the fascinating tale rise and fall of George Jung, who became one of the biggest drug dealers in the US. The film chronicles his rise as well as his increasing efforts to allude the police tracking him.

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.

Buy this limited edition, original cinema movie poster of this award winning film and check out this signed Leonardo DiCaprio photo of Leo DiCaprio doing pushups during the film.

If you loved The Departed, you should check out this other complex Boston drama, Mystic River. This Clint Eastwood directed film follows the story of three friends that drift apart after a tragedy in their younger years. When tragedy strikes one of their kids they are thrown back together. This is an all star cast in an excellent film.

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