There’s no denying that since exploding onto the Silver Screen in the 90’s with films like The Basketball Diaries, Romeo and Juliet and Titanic, that Leonardo DiCaprio has been the largest actor in the world and really the best actor of his generation. Almost every film, especially since the millennium, that he’s starred in is a classic (or at least certified fresh on Rotten Tomatoes) and despite all of the great work that he’s done he only recently won his first Oscar (for the film The Revenant). The streak of him starring in films that were both financially and critically successful has only really been rivaled by 90’s era Will Smith. He’s an old school Hollywood star living in present day and he’s got a great eye for projects both as an actor and as a producer. He’s also branched out into documentaries about a passion project of his, the environment. He’s actually made great strides there as he recently brought a ton of attention to the plight of these adorable mini-dolphins that were near extinction near South America. So, outside of being the best actor around these days he’s also a great guy, so with that in mind let’s break down his ten best roles/films! Keep in mind that these are his best films, not his best roles. While the two are closely related it’s more about what films of his are great.
10. Gangs of New York
Martin Scorsese is perhaps best known for his films about the Mafia than any other director out there (even The Godfather‘s Francis Ford Coppola), thanks to amazing films like Goodfellas and Casino starring his one-time muse and go to guy, Robert De Niro. With his most ambitious film about the gang lifestyle, Scorsese worked with Leonardo DiCaprio for the first time back for the 2002 release of Gangs of New York which went way, way back (for a Scorsese film) and discussed the gang culture that permeated New York City around the time of the Civil War. The movie is an epic period drama that focuses on the gangs that were vying to control the “Five Points” area of Manhattan back in the 1860’s and more than anything showed that really nothing has changed all that much outside of technology. The film was really a departure for DiCaprio, as well, as it was less about his youthful good looks and more about his serious acting chops. Because of that it’s probably one of the more important films in DiCaprio’s filmography, as if the film wasn’t received well perhaps he’d never work with Scorsese again and we’d have missed out on countless amazing films. Thankfully that wasn’t the case and the film ended up being nominated for Nine Academy Awards, including best Actor for Daniel Day-Lewis, an award that he somehow didn’t win. The movie was based on real gangs and real people and while they stretched the truth to make it, it’s still an amazing peak into the seedy underbelly that America grew from underneath and again, really shows that not much has changed in terms of xenophobia and hatred, except for perhaps the colors of the skin(s) of the people that are hated.
9. The Revenant
The Revenant is the type of movie that you really only want to see once as it’s definitely a must-see film but it’s just so depressing and bleak that you don’t really know if you want to watch it again (think: Requiem for a Dream). The film that finally gave DiCaprio the Oscar that he deserved for nearly every film on this list, the movie was a gigantic hassle to film as the writer/director Alejandro G. Inarritu demanded to work with natural light so sometimes they could only film for 20 minutes a day. Keep in mind that the movie was filmed on location in the actual wilderness, in the actual cold as well (and the fact that because of global warming it was hard to find any actual snow in Canada so they had to fly down to the top of a mountain in South America to find snow) and you’ll know why this film forced the actors and crew to really bond to survive. It’s really a testament to how tough people used to be, showing about as realistic a film in terms of the life of a fur trader as any. While there were numerous inaccuracies in the film it was actually based on the life of a real man who did indeed seek revenge after he was mauled by a bear and left for dead by a couple of the men in his fur trapping party. The film added a son that was also murdered but for the man the film was based on, frontiersman Hugh Glass, the fact that he was left for dead and his furs were stolen was more than enough of an impetus for a cross-country revenge trek. The reason that this film isn’t higher on this list is because it does delve into the artsy territory a bit too much and because it’s also one of the first films that has used natural light so it’s sort of hard to watch at some points as well. But, DiCaprio (and his co-star and source of all of his hatred, Tom Hardy) gives the performance perhaps of his life and definitely deserved the Oscar for a film that nearly gave him hypothermia. Well done, Leo, well done.
Leonardo DiCaprio will perhaps always be most well known for the film Titanic, which came out in December of 1997 and absolutely took over the world. The film hit at just the right time and combined a fictional love story with the disaster that was the Titanic and while it’s budget ballooned and executives from Fox furrowed their brows in disapproval, writer/director James Cameron knew exactly what he was doing and while the film was the most expensive ever shot at that point in time, it made it’s money back in spades and at the end of it’s run ended up as the most successful movie of all-time (until it was topped by another Cameron film, Avatar, about 12 years later (and then Star Wars: The Force Awakens a little after that)). James Cameron loves the deep, deep ocean and actually holds records for the deepest solo dives (in submersibles, of course) himself. He actually was the one controlling the submarine(s) at the beginning of the film and got all of that footage himself. He has said in interviews since that he really only wrote the movie so Fox would give him a budget to pursue his passion/hobby, which was diving deep into the ocean and attempting not to die. More than the deep ocean, at least initially, his fascination growing up was with shipwrecks and he referred to the Titanic as the “Mount Everest” of shipwrecks, obviously. So, he wrote the script hoping that he’d get money to visit and pitched it to Fox as “Romeo and Juliet on the Titanic”, which makes a lot of sense when you look at the fact that the two lovers in the film came from two different worlds and that those around them would never let them be together. Considering the fact that DiCaprio was fresh off of filming the 90’s remake of Romeo and Juliet, he obviously made a lot of sense as the lead role in the film. Cameron is a well known control freak though and apparently he rubbed someone the complete wrong way while the film was being… Filmed. At one point someone laced some of the catered food with LSD, which made a ton of people sick and probably also gave them some strange dreams. Say what you will about his approach but he definitely delivered a film that will be remembered forever, it was also nominated for basically every Oscar imaginable (14 in total), winning 11 of those and either tying or breaking records critically and commercially. Both Leonardo DiCaprio and Kate Winslet have had amazingly successful careers after Titanic and have even starred in another film together that didn’t make this list. It essentially can be thought of as what would’ve happened if Jack and Rose both survived, moved to the suburbs and had a loveless marriage, it’s titled Revolutionary Road and it’s hyper depressing but really well done as well.
7. The Aviator
Leonardo DiCaprio has a penchant for making biographical films, mostly because he’s worked with the legendary director Martin Scorsese a ton and Scorsese tends to make films about real people (see: Howard Hughes, Jordan Belfort, even the upcoming H.H. Holmes film), outside of the Scorsese films though DiCaprio has starred in films like Basketball Diaries which is based on the memoirs of a heroin addict and as J. Edgar Hoover in the film, J. Edgar. The best example of this, really, is his role as Howard Hughes the famous Aviator in… Aviator. The film was a gigantic undertaking about one of the most famous American’s of all-time and it covered most of Hughe’s amazing life from how he got his start to his countless romances with Hollywood legends, to his eventual descent into madness thanks to an unchecked and severe case of obsessive compulsive disorder. If you want to see DiCaprio at his best this is perhaps the film to do it, as the nuances of playing a man who is super brilliantly but slowly losing the mind that had gotten him so far is both breathtaking and sad. It’s also a travesty that DiCaprio didn’t receive the Oscar for this film and it was around this time that the idea that perhaps the Academy had something against DiCaprio caught flight. Get it? Flight? Cause… Planes!
6. Romeo and Juliet
1996’s Romeo and Juliet very well could’ve been the reason that DiCaprio ended up starring in Titanic as writer/director James Cameron essentially pitched Titanic to Fox Executives as “Romeo and Juliet on the Titanic”. Marketed as essentially a modern retelling of one of the most famous stories in the history of the world, Romeo and Juliet was directed by Baz Luhrman and was written, obviously, by William Shakespeare. While the setting was contemporary the movie was essentially word for word from the play itself with modern elements (their “swords” were guns that they called swords, they drove low-riders instead of horses and they were really just in competing gangs in a town called Verona Beach, as opposed to the Verona from the play). It actually works, even if it’s pretty hard to understand from time to time (as the people are speaking in what amounts to poems) but it, like a lot of Luhrman’s work (See: The Great Gatsby) is visually amazing and also extremely well done. While DiCaprio was a decently known actor at the time and was very respected as well (his role in Basketball Diaries was amazing) this was the film that launched him into the stratosphere as an actor. It was the first of his “dreamboat” roles and he absolutely nailed it, starring opposite “My So Called Life” star Claire Danes. The movie is really great and something that every Shakespeare fan should watch at least once and really more than any other film on this list is responsible for DiCaprio’s career so it gets a spot on this list (as opposed to other “better” films like Blood Diamond) because of that as well.
5. The Great Gatsby
Speaking of visually stunning remakes of classic stories, Baz Luhrman and Leonardo DiCaprio teamed up yet again in a movie version of the classic novel by F. Scott Fitzgerald. For those not familiar, it’s the story of a young writer who moves into a shack that happens to be next door to the home of a super young, attractive and rich man named Gatsby. Many people don’t realize if Gatsby exists because he throws these lavish and expensive parties every weekend (This is during the roaring 20’s, mind you, when drinking was illegal, which is where Gatsby get’s his money as he’s a bootlegger) in the hopes that the woman who lives across the lake (who happens to be his pre-war lover) will come by and fall back in love with him. Because that woman is the cousin of the main character, he ends up getting roped into a story that ends pretty tragically. It’s a great book and the movie definitely does it justice (which isn’t something that you can say about every adaption of that book). It’s a visual spectacle that takes complete advantage of new technologies and the soundtrack is amazing as it combines current hip-hop (namely Jay-Z and Kanye West) into music that sounds like it’s straight out of that decade/era. Leonardo DiCaprio is perfectly cast and it’s the second time that he stars opposite Michelle Williams, who plays his lost love here and … His lost love in our next entry, the psychological thriller Shutter Island.
4. Shutter Island
Psych! Turns out that’s not Michelle Williams in the Great Gatsby but her look-alike, Carey Mulligan! They’re both blonde and really do resemble one another but the actual point of that “joke” was to show that sometimes not everything is as it seems. That’s really the theme of Shutter Island, yet another film that paired DiCaprio with Martin Scorcese and outside of The Departed this may be their finest work together. It’s the type of movie, also like The Departed, that has an ending that is probably Top 3 in the past 20 years in terms of twists (alongside The Sixth Sense) as it turns out that (SPOILER ALERT) DiCaprio’s character is actually the man he’s been looking for the entire movie and that he’s essentially a patient at the island for the “Criminally insane” himself. It’s a twist that you really don’t see coming and the entire movie is just super beautiful, while also being super, duper sad. The movie is really about loss and how the mind copes with it while also doing it’s best to show that perception really can be reality. There are countless examples of things not being as they seem, with a shot where a woman is handed a glass of water but when she’s drinking it her hand is empty. It’s a cool way to show that the human mind can play tricks on itself and because of DiCaprio’s performance you really end up believing that his character has been through so much that he just can’t handle it anymore, whether he makes that decision at the end consciously or subconsciously, you definitely feel for him and really are just glad that his suffering is over at the end, even if it’s incredibly depressing regardless.
3. Wolf of Wall Street
Speaking of a depressing ending, the life of The Wolf of Wall Street himself, Jordan Belfort, is told in this additional entry into the DiCaprio/Scorsese pantheon that like so many others is the story of a real person’s life. This is shot as a classic Scorsese film, which much of the first Act being narrated by the main character and it delves into crime (also like many Scorsese films do) but this time it’s white collar crime. His character is addicted to cocaine and Quaaludes in the film and the scene where DiCaprio tries to get to his car and drives home shows just what a great actor DiCaprio is as he’s essentially half paralyzed and you believe it (even if it’s hilarious). This movie is also responsible for breaking Margot Robbie and she does a great job rocking the Long Island accent necessary in the film, which is surprising as really she was mostly known for the Australian soap opera Neighbors up until that point and you wouldn’t think that someone on that show could pull of such a difficult accent (a lot of people can do it but it turns into an impression rather than a real accent). Alongside DiCaprio is Jonah Hill, who actually gained weight back for the film and apparently worked for around $6-,000 dollars as the budget wouldn’t allot for his role in the film but he wanted to work with Scorsese so he basically did it for next to nothing after taxes (by Hollywood’s standards). Unfortunately the movie was funded by money meant for the “Malaysian Wealth Fund” and a massive criminal investigation took place that ended up forcing DiCaprio to return gifts he had received from the producers of the film, outside of that it’s also known for the most uses of the “F-word” of any movie in the history of cinema, something I’m sure Quentin Tarantino responded to by saying… “F***!”
Shutter Island was all about perception and reality and that’s the theme of another movie that was extremely revolutionary and ground-breaking in it’s own right, Inception. Written by the Brothers Nolan in between The Dark Knight and The Dark Knight Rises, Inception is a modern classic that made tons of money but also showed that every Blockbuster needn’t be either part of a franchise or based on comic books. The movie is all about dreams and the manipulation of dreams and in classic Nolan fashion there is a definite cliff-hanger ending that still to this day has people online discussing what they believe it means. A visual spectacle as well, the movie was extremely influential and has been copied since, most notably by Marvel’s Doctor Strange in 2016. The movie was also perhaps most influential in the trailer/soundtrack game where it’s usage of the “BLARRRRMMM!” sound was copied by every action movie afterwards, up until really recently (where it’s been replaced with a slowed down/sad version of an otherwise innocent or children’s song). Inception isn’t the super dramatic type of film that DiCaprio typically goes for but it will definitely go down as one of his more famous roles, you have to think that he made the film after wanting to work with the Nolan’s, but one has to hope that he’ll work with them sometime in the future as well. Considering the fact that Scorsese is being courted to produce the upcoming Joker stand-alone film (in the hopes that he will be able to convince DiCaprio to take the role), one has to get excited by the very idea of a Scorsese- Nolan- DiCaprio film about the Joker. That’d be the best movie of all-time! Make it happy, DiCaprio!
1. The Departed
What movie tops Inception, you ask? Well, that’s simple, because it’s the best movie to be released this century/millennium (outside of perhaps the aforementioned Dark Knight). The Departed is ANOTHER Scorsese/DiCaprio collabo and it’s really an ensemble film more than anything else. Starring Jack Nicholson, Matt Damon (“Matt Damon!”), Mark Wahlberg and Leonardo DiCaprio, as mentioned in the Shutter Hill write up, The Departed has one of the most surprising, amazing and memorable endings of any film really ever. Taking the title of the film quite literally, the ending shows that essentially everyone dies (outside of Wahlberg, who some believe was the THIRD rat in the department which makes zero sense and should enrage anyone who has A) Seen the film and B) Has a brain). This is the movie where people really started thinking that DiCaprio was being robbed during Oscar time as Mark Wahlburg, who was really just playing himself in the film, was nominated for an Academy Award while DiCaprio (the main character, with arguably the toughest role in the film) wasn’t. Either way, though, this movie is peak Scorsese/DiCaprio and it was so good that it essentially ended up creating a role for Johnny Depp in 2016’s Black Mass. Both films were either based (loosely or completely) on the life of James “Whitey” Bulger, who was actually still on the lam during the shooting and release of The Departed, which is something the families of his countless victims didn’t really like very much. It’s a classic mob story, though, and those stories have been fleshed out so deeply that even Scorsese had to start focusing on Irish mob movies! The Departed, being filmed in Boston, is just an amazing movie with great twists and turns and it’s definitely the best DiCaprio movie (so far). Hopefully the next collaboration between DiCaprio and Scorsese can top it, as they’re working on a film version of the novel A Devil in the White City. Which is the story of “America’s First Serial Killer” a man known as H.H. Holmes, who opened a hotel of horrors across the street from the World’s Fair in Chicago back in the 1890’s. The man was murdering people for their bodies/skeletons (so he could sell them for medical testing) but it was about more than the least efficient way to make money ever as his hotel was basically a torture museum. That movie is set to be released in the next few years so definitely keep an eye, and a… Skelton (?) out!