Being Oscar weekend, it’s not surprising that Oscar related stories are dominating Google Trends. We have made our way through awards season and this is the big event! This past week, every news outlet was abuzz with stories on the nominees. Without a doubt, the standout nominee for the 2016 Oscars is Leonardo Dicaprio. Leo has had an illustrious career, ranging from humble beginnings on Growing Pains up to the unadulterated brutality within the Revenant, which he is nominated for this year. I am a lifelong Leo fan. I have seen all of his movies and I can honestly say, he rarely missteps in his choice of roles. He is a one of a kind gift to cinema, with his devotion to his characters and movie star good looks. After Titanic, he could have easily played the pretty boy role for the rest of his career, but he went off in a different direction and explored his craft with a wide variety of characters. In preparation for his big night ahead, I’ve ranked every Leo role, from the very beginning. Let’s step into our time machine and remember the incredible acting evolution that led Leo to (probably!) win his first Oscar today:
27. Total Eclipse
You probably haven’t heard of this movie. You aren’t missing much. Leo plays 19th century poet Arthur Rimbaud, who embarks on a passionate relationship with a fellow poet, Paul Verlaine. Leo is the only good thing about the movie, which is largely bogged down by a clunky script. But, if you are craving more Titanic era Leo, it might be worth a watch.
26. Critters 3
Leo?! In a Critters movie?! Yes, even Leonardo Dicaprio had to start somewhere. He didn’t always have the ability to cherry pick all of his roles. These movies haven’t aged well, but Critters 3 does provide a wonderful opportunity to see Leo in his pre-Titanic days. Skip watching the entire movie and just look up Leo clips online, to experience the throwback glory.
People get so caught up in Leo’s work with Martin Scorsese that they forget he has also worked with other legendary directors. This forgotten movie paired him up with Woody Allen. Post Titanic, being a part of an ensemble cast in a movie that covers celebrity culture probably mirrored Leo’s real life ascension into the spotlight, which is kind of cool. But, at the end of the day, this film is pretty forgettable.
24. The Man in the Iron Mask
A lot of people hate this movie, but I can see why Leo chose to take on a role like this, post Titanic. He was determined to prove that he wasn’t merely a pretty boy. Taking on the dual role of Louis XIV and his brother was quite a challenge! With a strong supporting cast (Jeremy Irons, John Malcovich, and others), and a plot that’s centered on royal betrayal and intrigue, The Man in the Iron Mask is worth a watch.
23. Don’s Plum
Many people consider this to be Leo’s worst high profile movie. His face was prominently attached to it, and it fell flat. But, I have an appreciation for it because it united Leonardo Dicaprio and Tobey Maguire on screen. Since Leo and Tobey are real life BFFs to this day, I’m a softie for the sentimental aspect of this movie. Leo and Tobey went on to have a golden era as members of the “Pussy Posse,” where they gallivanted around town bro’ing out and picking up chicks. Tobey has since gone on to get married and leave the playboy lifestyle behind. As seen in the media, Leo has not. But, if you want to revisit their glory days, check out this movie.
22. Body of Lies
Leo and Russell Crowe was an interesting matchup that I didn’t see coming. They star together in this overly dramatized spy thriller. Though it’s fun to watch Leo take down terrorists, this movie is never quite believable. It’s a conventional espionage thriller, and as a viewer, you would expect much more from Dicaprio and Crowe. It’s definitely not Leo’s worst movie, but it’s far from his best.
21. The Beach
Widely remembered as one of Leo’s only missteps in his career, many people are quick to dismiss the Beach as a movie that tries to do too much. This was Leo’s first movie after Titanic. People had out of this world expectations! I put it up higher on this list because people need to respect this movie for what it does well. Leo plays a young American backpacker who travels to Thailand with adventure on the brain, but he gets into far more trouble than he expected. This role foreshadowed where Leo’s career would go in the future, showcasing his affinity for playing emotionally tortured characters. It’s a guilty pleasure of mine. Most importantly, with his shirt off for a large portion of the film, Leo is total eye candy. Revisit it today and give it a fair shot.
20. Marvin’s Room
With such a great cast (Leonardo Dicaprio, Meryl Streep, Diane Keaton) you think you would hear more about this movie. But, it’s often forgotten about when people discuss Leo’s work. Covering a relatable theme of strained family dynamics, this movie packs an emotional punch. Streep, Dicaprio, and Keaton deliver. It came out the same year as the far more flashy “Romeo + Juliet,” so my guess it that is just got covered up by the press for that. With 3 incredible actors serving all the feels and more, it is definitely worth your time.
19. This Boy’s Life
Grab the tissues, because Leo will break your heart with this movie. In the film, Ellen Barkin matches up with Robert De Deniro. Now, Barkin’s son Leo has a new father figure, but he proves to have far less of a positive impact than anticipated. This film shines a light on the issue of domestic abuse within families, sharing an important social message. Leo fully commits himself to the role, going toe to toe with Robert Deniro, which is not an easy feat! This movie truly shows how incredible Leo’s talent was, and how far his career would go.
18. Growing Pains
I know, it’s not a movie. But, any reflection on Leo’s career deserves a mention of Growing Pains, the adorable TV sitcom on which Leo made his big debut in the public eye. Playing homeless teenager Luke Brower, Leo first captured my heart. And I have never let go. Though his recent movies have shown his dramatic intensity, this role showcased why he is also the epitome of a charmer. If Leo wants to teach me important life lessons, I will listen!
17. The Basketball Diaries
As mentioned previously, Leo has made a name for himself by playing emotionally tortured souls. But this is one of his first roles that proved how far down the rabbit hole he could go, in terms of psychological distress. I absolutely adore his portrayal of Jim Carroll, a once promising basketball star who succumbs to drug addiction. Leo was still a rookie when he took on this project, but it is widely considered to be one of the standout movies of his career.
16. Revolutionary Road
Kate and Leo! Kate and Leo! We want more Kate and Leo! Fans finally got their on screen reunion of Kate Winslet and Leonardo Dicaprio in this stunning period piece about a 1950s couple struggling to make their relationship work. Myself and many others have hoped that Kate and Leo would just “get together already” and be a couple in real life. Though that has never happened (*tear), this movie gave us an inside peek at what their married life could have been like, warts and all. Any time that Leo and Kate are together, I can’t control my happiness. Seeing the two of them united on screen again was pure magic. Kate Winslet won the Golden Globe for her role and the movie won over many hearts in America.
15. Blood Diamond
This movie got mixed reviews when it came out. Critics of the movie said that it failed when it came to storytelling, even though Leonardo Dicaprio was in fine form. I beg to differ. Though Blood Diamond is a fictional story, it is based on important real life facts, among them being the extreme way in which the diamonds in our jewelry stores are acquired. Leo, accompanied by a stellar Djimon Hounsou, does an incredible job bringing this story to life. Watching the film, I became invested in how much one rare diamond could change lives. In the process, I gained a whole new perspective on the world. If you haven’t caught this movie, I highly suggest you seek it out.
14. J. Edgar
Leo has a way with biopics. Throughout his career, he has proven that he has an incredible ability in honoring real life people with sizzling commitment on screen. This movie is sometimes overlooked. It’s not as flashy as some of Leo’s other roles. But, I think it’s one that should be remembered. The story of J. Edgar is fascinating on its own. Head of the FBI for 50 years, J. Edgar Hoover was one of the most powerful men in America, going to extreme lengths to keep his country safe. Fiery and bold, J. Edgar was the perfect role for Leo to put his stamp on. In particular, the chemistry between Leo and Armie Hammer, who plays J. Edgar’s secret lover, was quite moving for me to watch. On this particular movie, I stand firmly against the critical response. It deserves far more credit.
13. The Aviator
Another year, another biopic. This one, unlike J. Edgar, was very well received. As mentioned previously, Leo has made a name for himself by playing off kilter human beings. The more messed up, the better. The role of Howard Hughes would become one of his best and most lauded performances. Hughes was immensely successful in many arenas, romancing Hollywood leading ladies, producing big budget movies, and revolutionizing the aviation industry. But, beneath the surface, he suffered from crippling depression and several different phobias. Directed by Martin Scorsese, Leo took this role and ran with it, showcasing a level of depth to his acting that had previously been unseen. Since then, he has played other eccentric billionaires driven mad. But this was the first time he truly lost it, and I loved every minute of it.
Whenever a Leo movie launches a million memes, you know the cultural impact has been great. Armed with a tremendous cast and an exquisite vision by Christopher Nolan, Inception has left an indelible mark on cinema. The grounding concept, that we can get lost in our dreams and lose track of reality, though extreme, is something that many of us of can sink our teeth into. The entire movie was a mind fuck of extreme proportions, and it would not have achieved such great success without the emotional power of Leo at its core. One of my favorite aspects of this movie is that it proves Leo can excel in an ensemble cast; he doesn’t have to stand alone. And that is the sign of a phenomenal actor.
11. Django Unchained
This is a true Quentin Tarantino film. Violent and over the top, Django profiles life in the south two years before the Civil War. Tarantino created an incredible film that brings the South to life, not shying away from brutality. Leo, playing flamboyant slave owner Calvin Candie, takes a different approach in this movie, playing a true supporting role. By no means is he the star, but he steals every scene that he is in. It’s been made clear time and time again that Leo can carry a movie on his back. But with an incredible cast led by Jamie Foxx, he didn’t have to do double time here. His performance, though short and sweet, is SO impactful. And more humorous than his usual fare. I will pay good money to watch Leo camp it up.
10. Shutter Island
Digesting this list, there is a common trend of Leo playing tortured souls. Arguably, Shutter Island gave Leo the biggest platform to showcase his penchant for psychological madness. Playing US Marshall Teddy Daniels, Leo ventures to an insane asylum to track down an escaped murderess. Though he enters the asylum with his sanity in tact, he leaves a broken man. Watching his character unravel throughout the film is a harrowing experience. When Leo goes crazy, I can’t help but lose my mind right alongside him. Though this film wasn’t universally praised when it came out, I still think it’s one of Leo’s best roles.
9. The Wolf of Wall Street
I had the pleasure of watching The Wolf of Wall Street alongside my grandmother. I would not suggest that anyone do the same. Jordan Belfort made a huge fortune by defrauding wealthy investors. As he accumulated his wealth, he took on a ludicrous lifestyle defined by an excess of sex, drugs, and thrills. When Leo stepped into Belfort’s shoes, he utilized his affinity for playing charmers, but amplified his persona ten fold. Once again directed by his old pal Martin Scorsese, Leo brings Belfort to life, in all of his disgusting glory. With Leo in the role, Belfort becomes somewhat of a greek tragedy. In this movie, Leo elevates the material and gives a greater depth to the frat boy lifestyle. Though it was mortifying to experience that hedonistic journey alongside my grandmother, I can respect Leo for his honest portrayal.
8. The Great Gatsby
First off, The Great Gatsby is one of my favorite books, if not my favorite book. The themes that it covers are so relatable that now, decades after it was written, the book still resonates with readers. Baz Luhrmann had a great story to work with, and he made a very wise decision in casting Leo for the role of Jay Gatsby. Playing yet another eccentric billionaire, Leo makes you invest your love in Gatsby. Through his piercing blue eyes and seductive stare, Leo brings Gatsby to life and elevates the original source material. Close to 20 years after playing Jack Dawson, Leo proved that he could still play the pretty boy, but he could take it to the next level.
7. Gangs of New York
Marking the first time that Leo worked with Martin Scorsese, Gangs of New York depicts a revenge story in 1860s New York. Acting alongside legendary actor Daniel Day Lewis is never an easy task. But, Leo rose to the occasion, and provided a terrific foe for Lewis’ “Bill The Butcher.” Emotions run high in this film, which depicts messages about immigrants that can still be relevant in present day. Leo went toe to toe with one of Hollywood’s most awarded stars, and picked up invaluable tips on what it means to be a true “character actor.” Since then, Leo has only gotten better.
6. The Departed
I love this movie for so many reasons. Featuring Jack Nicholson, Matt Damon, and many other talented actors, Leonardo Dicaprio is the icing on the cake in this ensemble. It would be easy to get lost in such an impressive cast, but Leo shines. He loses himself in the role of South Boston cop Billy Costigan, showcasing a brutal honesty in his performance that shakes me to my core every time I watch it. Once again, this character is quite tortured, but in a different understated way. Unlike some of Leo’s flashier roles, you feel like you could really meet Costigan on the street, and you can relate to his internal struggle concerning his work. This movie is universally lauded, and rightfully so. It stands the test of time as one of Leo’s best.
5. Romeo + Juliet
Marking the first time Leo worked with Baz Luhrmann, Romeo + Juliet is a little bit of a guilty pleasure for me. Being a Shakespeare fan, I get excited any time a movie adaptation is announced. Coming out right before Titanic mania, this movie put Leo on the map, and established him as a hearthrob worthy of attention. His chemistry with Claire Danes is so on point, you can feel the sexual tension through the screen. I first saw this movie when I was 8, and therefore couldn’t relate to many of the deeper themes. But, watching it as an adult, I have a whole new appreciation for Leo’s scintilating performance. Taking on a role that has been played a million times before, Leo brought an approachability and sensuality to Romeo that is very special. Whenever this comes on TV, I always stop to watch and enjoy the magic.
4. Catch Me If You Can
I ADORE this movie. Once again proving that he can work for directors other than Scorsese, Leo teamed up with Steven Spielberg for this charismatic tour de force. Leo’s portrayal of infamous con man Frank Abagnale Jr. is so spot on, you forget that you are watching a movie. It feels like a documentary. Paired up with Tom Hanks, an incredible actor in his own right, Leo shines throughout the entire movie, growing up before our eyes on screen. In particular, Leo’s relationship with his on screen dad Christopher Walken is one of my favorite father son dynamics in cinema. As he has done many times in his career, Leo draws sympathy from the audience for his performance, even though his character is severely flawed. You shouldn’t feel sympathy for the con man, but you do. And that is because Leo gives him so much heart.
3. What’s Eating Gilbert Grape
Leo will (hopefully!) win his first Oscar tonight. But, many people believe that he should have won an Oscar for this role, which came together at the very beginning of his career. Portraying a mentally impaired boy with a knack for trouble, Dicaprio establishes himself as a young actor who is worthy of immense respect. In this movie, he goes toe to toe with Johnny Depp, who went on to become a highly accomplished actor. But, Leo steals the show. A certain sensitivity is necessary when portraying the mentally disabled. Leo approaches this role with so much respect and genuine personality that you can’t help but become invested in his character. This movie was a true sign of the greatness that was to come in Leo’s career.
2. The Revenant
For the highly talked about “bear scene” alone, this movie is worth the cost of admission. But, it’s so much more than that. Taking on the role of fearless 1800s wilderness adventurer Hugh Glass, Leo redefines what it means to be a character actor. Far from the pretty boy roles that he’s had in the past, Leo’s turn as Glass is a cinematic tour de force. For a large portion of the movie, Leo’s character is unable to talk, something that many actors would be terrified to take on. But Leo accepts the unique challenge with gusto, driving the majority of the movie with only body language. In the process, Leo proves that he doesn’t need to rely on a script to give a powerful performance, ascending into a new stratosphere of acting talent. I knew this movie was a Western. I knew it would be long. I knew it would be a journey. Backed by remarkable cinematography and direction by Alejandro Innaritu, this movie is a rare gem of emotional and technical achievement. I fully committed to Leo’s journey, and thoroughly enjoyed myself. If you haven’t witnessed the cinematic majesty of the Revenant, I highly recommend that you seek it out.
I knew who Leo was prior to Titanic. I watched him on Growing Pains and I enjoyed Romeo + Juliet in the theater. But, there is a reason why so many industry professionals separate Leo’s career into pre Titanic and post Titanic sections. Leo existed before Titanic, but he never would have become the monumental pop culture icon that he is today without Titanic. Titanic is my favorite movie of all time. Yes, it’s cheesy. Yes, there are multiple continuation errors throughout (I learned that through my special edition DVD). But all flaws aside, it is a cinematic treasure, and it changed the way that movies are made. With Titanic, James Cameron busted the movie making industry wide open, with state of the art special effects and a love story for the ages. And he enlisted the perfect leading man in Leonardo Dicaprio. This is the role that put Leo on the map. This role made you want to care about Leonardo Dicaprio. And I hope that Leo will reference this iconic role when he gives his long deserved Oscar speech tonight.