A Cinematic Journey Through Leo’s Award-Winning Masterpieces at the Academy Awards

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Free Download Top Leonardo DiCaprio Oscar Winning Movies

Written by Kaylee Wood | Last updated: April 29, 2020

Here lists all Leonardo DiCaprio movies/films of which some deserve Oscar Award yet haven’t, and you might have missed out. So let’s just jump in the Leonardo DiCaprio Oscar winning movies round-up and pick the one you like to free download and watch.

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What Are the Top Leonardo DiCaprio Oscar Winning Movies?

Here is the list of Leonardo DiCaprio movies that starred him on screen. The movies produced by him, like Orphan, are not in this list. So, let’s see what are the top Leonardo DiCaprio movies worth downloading and watching:

Note: movies with red-colored title are those that earned Leonardo DiCaprio Oscar nominations.

The Quick And The Dead (1995)
IMDB: 6.4/10
Rotten Tomatoes: 56%

Maybe a bit overtly cliché, but if you are fond of American western film and epic gun fight, this movie of Leonardo DiCaprio will satisfy your specific taste buds. Though not a Leonardo Oscar winning movie, the Quick & the Dead presented a crazed compilation of highlights from famous westerns.

Critters 3 (1991)
IMDB: 4.2/10
Rotten Tomatoes: 23%

Though this cheap horror comedy movie is lame and simple plotted, it witnessed Leonardo DiCaprio’s debute performance and thus is credited by DiCaprio fans as a must-see movie. You will end up sighing how fast time flies.

This Boy’s Life (1993)
IMDB: 7.3/10
Rotten Tomatoes: 75%

This drama is moving and harrowing, dipicting the harsh relationship between members in a step-family. You can download and watch the breakout performance - the fight scene between young Leonardo Dicaprio and his step-father Robert DeNiro. Good film, worth seeing!

What’s Eating Gilbert Grape (1993)
IMDB: 7.8/10
Rotten Tomatoes: 89%

This collaboration of Johnny Depp and Leonardo DiCaprio is also a must-see movie for both Depp & DiCaprio idolaters and movie hunters. DiCaprio was, for the first time, nominated by Academy Award for Best Supporting Actor relying his great performance in this film. “A performance of astonishing innocence and spontaneity, bringing a touching credibility to a very difficult part“ - to DiCaprio’s performance.

The Quick And The Dead (1995)
IMDB: 6.4/10
Rotten Tomatoes: 56%

Maybe a bit overtly cliché, but if you are fond of American western film and epic gun fight, this movie of Leonardo DiCaprio will satisfy your specific taste buds. Though not a Leonardo Oscar winning movie, the Quick & the Dead presented a crazed compilation of highlights from famous westerns.

The Basketball Diaries (1995)
IMDB: 7.3/10
Rotten Tomatoes: 76%

See how our hero Jim(Leonardo DiCaprio), a promising basketball player, became addicted to drugs and ended up in incarceration. How he struggled before prostituting himself? This is a moving coming-of-age crime drama that might recall our experiences. And Leo gained public recognition for this movie.

Total Eclipse (1995)
IMDB: 6.5/10
Rotten Tomatoes: 61%

This romance movie of Leonardo DiCaprio presents passionate and then hostile relationship between 2 19th-century poets. You will love how inner rebellion breaks out from the confine of a gentlemen-suit.

Romeo + Juliet (1996)
IMDB: 6.8/10
Rotten Tomatoes: 77%

DiCaprio won the Silver Bear Best Actor, BEA Favorite Actor, BIFF Best Actor for his performance as Romeo, so you surely shouldn’t miss this Leonardo romantic movie and his golden age, needless to say how handsome he was in this film.

Marvin’s Room (1996)
IMDB: 6.7/10
Rotten Tomatoes: 80%

This all-star cast Leonardo DiCaprio film tells another touching story about family - A leukemia patient (Meryl Streep) attempts to end a 20-year feud with her sister to get her bone marrow. This might be the first time Leonardo started to play a role with mental illness. See how he dealt with the character!

Titanic (1997)
IMDB: 7.7/10
Rotten Tomatoes: 88%
Love beyond death and life. Epic-making romantic movie of Leo. Everybody should have watched this.

The Man In The Iron Mask (1998)
IMDB: 6.4/10
Rotten Tomatoes: 33%

The ratings for this movie is relatively low, but due to DiCaprio’s post-Titanic boost in popularity, the film got a finacial success. DiCaprio won a Golden Raspberry Award for Worst Screen Couple for his interactions as twins in the film. So look carefully how he portrays the two characters.

Celebrity (1998)
IMDB: 6.4/10
Rotten Tomatoes: 41%

Directed by Woody Allen, filled with beautiful and famous faces, this DiCaprio joined movie is less as good as other Woody’s films like Deconstructing Harry.

The Beach (2000)
IMDB: 6.6/10
Rotten Tomatoes: 19%

A solitary beach paradise exploration, our Leo set out to find it with a map in Thiland. Gorgeous cinematography, yet with unfocused and muddled plot, if you do not mind that, this would be a good Leonardo DeCaprio movie to kill time.

Don’s Plum (2001)
IMDB: 5.9/10
Rotten Tomatoes: –

DiCaprio and Macguire, a gay romance? Nah. But in this low-budget black and white indie film, you can see how Leo portrays an annoying, selfish try-hard guy that seeks attention from a group by whatever means necessary.

Catch Me If You Can (2002)
IMDB: 8.0/10
Rotten Tomatoes: 96%

Directed by Steven Spielberg and stars Leonardo DiCaprio and Tom Hanks, this is one of the must see crime drama films of Leo, since this movie might be the one that paved the for DiCaprio’s later works. He won GGA Best Actor for the performance.

Gangs of New York (2002)
IMDB: 7.5/10
Rotten Tomatoes: 75%

Want to see the Best Kiss at MTV Movie Awards? Leonardo presented it in this movie. This film earned Leo 2 nominations at the 2003 MTV Movie Awards. And in regard of the movie, Gangs of New York was nominated for a total of ten Academy Awards at 75th Oscar.

The Aviator (2004)
IMDB: 7.5/10
Rotten Tomatoes: 87%

Nominated for a total of 11 Academy Awards at 77th Oscar and winning 5, The Aviator was truely a facinating piece of art. The movie earned Leo the Best Actor nonimation for the 2nd time, 1st time in a Leading Role. However, the commitee was too blind to give that award to him. He won MTV Movie Award for Best Male Performance.

The Departed (2006)
IMDB: 8.5/10
Rotten Tomatoes: 94%

This movie won 4 Academy Awards for Best Picture, Best Director, Best Film Editing and Best Adapted Screenplay at 79th Osacr. With or without Leo’s participation, this is totally an Oscar winning movie worth watching. The movie earned Leo that year’s GGA for Best Actor nonimation and IFTA for Best International Actor.

Blood Diamond (2006)
IMDB: 8.0/10
Rotten Tomatoes: 62%

This movie directed by Edward Zwick, was nominated 5 Academy Awards at 79th Osacr including Best Actor for DiCaprio (3rd time nonimation), yet won none. However, Djimon Hounsou won serveral other smaller awards for Best Supporting Actor. This is a fast paced, adventure packed piece of film-making you should see.

Body of Lies (2008)
IMDB: 7.1/10
Rotten Tomatoes: 54%

A can-do Leo’s action-spy movie that relied heavily on Leonardo and Russell Crowe’s convincing performance.

Revolutionary Road (2008)
IMDB: 7.3/10
Rotten Tomatoes: 67%

Leonardo was in peak state in this movie, bringing layers of buried emotion to a defeated man that you can even sense the change of nuance. He was nominated by DFCS/GGA/PSIFF/Satellite Awards etc. for Best Actor.

Shutter Island (2010)
IMDB: 8.1/10
Rotten Tomatoes: 68%

This neo-noir psychological thriller film brought Leo the Best Horror Actor nomination of Screem Awards in 2010, Best Actor nomination of Saturn Awards. DiCaprio won Teen Choice Awards for Choice Movie Actor: Horror/Thriller for this movie.

Inception (2010)
IMDB: 8.8/10
Rotten Tomatoes: 91%

Smart, innovative, and thrilling, this science fiction heist thriller film must be the best ever summer blockbuster of 2010. Leo won Scream Awards for Best Sience Fiction Actor in 2010 because of this movie.

J. Edgar (2011)
IMDB: 6.6/10
Rotten Tomatoes: 43%

J. Edgar brought Leonardo DiCaprio 8 Best Actor nominations. Movie itself won Top Ten Films awards by American Film Institute and National Board of Review.

Django Unchained (2012)
IMDB: 8.5/10
Rotten Tomatoes: 88%

This is a masterpiece directed by Quentin Tarantino, winning him Academy Award, a Golden Globe, and a BAFTA award for writing the film’s original screenplay. Leonardo also earned the National Board of Review Award for Best Supporting Actor.

The Great Gatsby(2013)
IMDB: 7.3/10
Rotten Tomatoes: 48%

Leonardo DiCaprio’s movie of romance was back again. Want to feel his charm as a middle-aged lover? Watch this then, as Leo did a great job for his role. He won Poeple’s Choice Award for Favorite Dramatic Movie Actor, Rembrandt Awards for Beste Buitenlandse Acteur and AACTA Award for Best Actor because of this effort in the movie!

The Wolf of Wall Street (2014)
IMDB: 8.2/10
Rotten Tomatoes: 77%

Produced by and starring Leonardo DiCaprio, this movie get Leonardo DiCaprio nominated for Academy Awards Best Actor for the 4th time, yet still without winning. Leo’s performance was highly praised by mass media, which earned him Critics’ Choice Awards and Golden Globe Awards for Best Actor. The movie also won MTV Movie Award for Best WTF Moment.

The Revenant(2015)
IMDB: 8.2/10
Rotten Tomatoes: 82%

Here at last, this epic historical adventure Oscar winning film brought Leonardo DiCaprio to his throne of Oscar Best Actor. And his long distance race for this Academy Award is finally over. This movie won 3 Award at 73rd Golden Globe Awards, received 12 Academy Award nominations, won five awards at 69th British Academy Film Awards and gained two awards at Critics’ Choice Awards.

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