The 10 Best – Leonardo DiCaprio movies (updated…where will INCEPTION rank?)

One of the best actors of our generation

From early on in his career, it was evident that Leonardo DiCaprio had acting chops.  What was not known, however, was just how good those chops were.  Leo has starred in some of the biggest films ever made and has managed to do stellar work in smaller, critically praised films.  One thing that you know you will get while watching a Leo movie…an incredible performance.  He has worked with the highest profile directors in the business, and like Johnny Depp, is one of the most sought after actors in Hollywood today.  Compiling a top 10 list for DiCaprio was not easy, but I think you will agree that these films are the true highlights of his acting resume.

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10. Shutter Island - Seems like working with Martin Scorsese is a great things for an up and coming actor.  And it’s obvious that Mr. Scorsese enjoys working with Leo.  They have done four films together (all but one of which made my list).  This creepy film is about U.S. Marshal Teddy Daniels investigating the disappearance of a murderess who escapes from a hospital for the criminally insane and is presumed to be hiding on the remote Shutter Island.  Once the investigation begins, you begin to wonder is Daniels losing his mind, or is it a plot to keep him on the island forever.  It is a well made film with, once again, fine supporting players.  It keeps you guessing until the last series of events, and even when it’s over, you still question the result.  DiCaprio does the ‘losing his mind’ thing pretty well. Rating:

9. William Shakespeare’s Romeo & Juliet -Not everyone was a fan of this version of Romeo and Juliet.  I thought it was an interesting take on the classic story, and Baz Luhrmann’s direction and inventiveness was key to making it work for a new generation.  Claire Danes was great as Juliet, but DiCaprio was the stand out, as he embodied the lovesick Romeo to perfection.  A strange, daring film that was highlighted by cool set pieces and decent action sequences. Rating:

8. The Quick and the Dead – One of my guilty pleasures.  I love this film.  It is so over the top with it’s violence set in the Old West that you can’t help but enjoy it.  It was promoted as a Sharon Stone/Gene Hackman film back when it came out, but two other stars would emerge the most memorable from this film.  Russell Crowe and DiCaprio.  Leo is so likable as the young gunslinger who thinks he is faster than anyone around, that when it comes to his ultimate demise, you hate that he’s one of the characters that has to go.  Hackman is great in this as well, and even Stone has some redeeming scenes.  But it is Sam Raimi’s direction and Leo’s performance that makes this a must see. Rating:

7. What’s Eating Gilbert Grape -Two of the greatest actors of our generation in one film.  At the time of it’s release, Gilbert Grape was billed as a Johnny Depp film, and deservedly so…he is the title character.  But what a lot of people didn’t know going in was the performance they were about to see from DiCaprio.  He steals every single scene he is in, and it is a career defining performance.   Not to mention Leo also received an Academy Award nomination for his work. Rating:

6. This Boy’s Life – The story is about the relationship between a rebellious 50s teenager and his abusive father, based on the memoirs of writer and literature professor Tobias Wolff.  Acting alongside Robert DeNiro is no easy task, but DiCaprio holds his own and even upstages DeNiro quite often throughout the film.  Some consider this to be his best performance, and I can see why.  This is a very disturbing, shocking movie that at times is difficult to watch.  There is no mistaking the lasting effect is has on you after you view it, and the performances stay with you as well. Rating:

5. The Aviator – Portraying Howard Hughes would be no easy task for any actor.  The man was brilliant, quirky, strange, and tragic the majority of his life.  Director Martin Scorsese tackled this material with a vengeance making the film one of the best of his career.  It was a lavish production that emodied exactly the life that Hughes was living.  The ups, downs, happy times, and the trainwrecks that defined Hughes was recreated perfectly by DiCaprio.  He was amazing in this film, and the supporting cast, especially Cate Blanchett, shines as well.  It is a must see film for many reasons, but just watching Leo bring the oddity that was Howard Hughes to life is alone worth the price of admission. Rating:

4. Catch Me If You Can - The ultimate trio.  Leo, Tom Hanks and Steven Spielberg.  The result – a wonderful film.  Not a normal Spielberg film, Catch Me If You Can was based on the true story about Frank Abagnale Jr. who, before his 19th birthday, successfully conned millions of dollars worth of checks as a Pan Am pilot, doctor, and legal prosecutor.  DiCaprio captured the innocence within the guiltiness of the young con artist.  He makes you feel bad for Frank.  Tom Hanks does exceptionally well too, and Spielberg directs the film with the right touch that allows the relationships between all of the characters to stand out. Rating:

3. Inception – (see review on our site!!) I knew this film would make the Leo top 10, but I wasn’t sure how high it would go.  Very minor flaws aside, this film is a true ‘thinking person’s’ movie.  It’s one of those rare films that you have to pay attention to nearly every single frame to keep up with what’s going on.  The dream within the dream within the dream plot can get confusing for some, but can also be very mind stimulating for others.  I’m not saying this film is just for the highly intellectual.  I’m just saying that when it comes to cinematic entertainment, some people prefer simpler ideas and mindless fun.  This is not that film.   DiCaprio’s performance carries the film, as he is the key character to what makes the film work.  Christopher Nolan is quite possibly the most creative mind in the movie business today, and it would be a crime if the film does not win Best Original Screenplay at next years Oscars.  It’s a combination of Memento and The Dark Knight.  The result = 2 and 1/2 hours of a cinematic getaway you will never forget. Rating:

2. Titanic – The box office champion…before Avatar.  James Cameron has a reason why it takes him so long to complete a film – his attention to detail.  Not only is this film visually stunning but what made audiences come back again and again was the relationship portrayed by the two lead actors.  The chemistry between Jack (DiCaprio) and Rose (Kate Winslet) is undeniable and the picture is carried by that.  Yes, the sinking of the ship is breathtaking, but the film would have just been another great looking disaster piece without Leo and Kate at the top of their game. Rating:

1. The Departed - I may get some argument on this one.  I love this film.  It’s an ensemble piece that is packed full of great acting performances.  The reason why I like DiCaprio so much in this film is because his character is the key element that ties everything together.  As Billy Costigan, you feel bad for this guy who is caught in the middle between the mob guys and the shady cops.  His character never stands a chance, and DiCaprio’s range shines through in the final parts of the film.  In my opinion, the movie really excels in the final act.  It’s Scorsese…a modern Scorsese.  And it’s nearly as good as the old school Scorsese.  Rating:

We have a lot more to look forward to from Leonardo DiCaprio.  Projects in the works include Hoover (directed by Clint Eastwood – based on the life of J. Edgar Hoover), Prisoners, The Wolf of Wall Street, and possibly, Aquaman.