My Favourite Leonardo DiCaprio Movies of All-Time

Few actors in Hollywood that achieved fame years ago are as beloved as Leonardo DiCaprio. Ever since his stardom in the 1990’s, DiCaprio has become one of the greatest actors in the film industry. With his charismatic personality, larger-than-life presence and commitment, DiCaprio has proven to be an icon in the world of entertainment. Arguably, DiCaprio’s greatest strength as an actor is his versatility. From Wall Street stockbrokers to star-crossed lovers aboard doomed ships, DiCaprio has proven that he can play various characters. Given the number of movies the actor has appeared in, creating a top 10 list isn’t easy. Nevertheless, listed below are my picks for the greatest movies made by an actor that deserves to be celebrated.

1. The Wolf of Wall Street

When it comes to the most controversial stockbrokers in American history, it’s worth discussing Jordan Belfort. A Wall Street stockbroker, Belfort engaged in reprehensible criminal behaviour causing his career to end in disaster. He engaged in a hedonistic lifestyle of partying, drug use and sex addiction. In 2013, Belfort’s life story was beautifully brought to the big-screen in “The Wolf of Wall Street”. In arguably the greatest role of his career, DiCaprio transforms into a real-life stockbroker that committed reprehensible crimes without any fear. It’s a role that allows the actor to capitalize on his charisma to portray a stockbroker that changed America. Whether he’s delivering a speech to employees in the workplace or mocking FBI agents, DiCaprio effectively uses his comic timing to create a character that’s compelling. Not only does DiCaprio capture the stockbroker’s personality but he completely commits himself to the role physically. The sequence in which DiCaprio drags himself to his Lamborghini high on drugs is the one of the greatest scenes the actor has ever filmed. Ultimately, what makes “The Wolf of Wall Street” DiCaprio’s greatest role is its complexity. He pulls off the tricky feat of making a corrupt criminal sympathetic. It’s a phenomenal performance from one of the world’s greatest actors that proves he thrives when playing complex characters.

2. Django Unchained

Leonardo DiCaprio has always fit perfectly in the role of a hero. DiCaprio has spent a large part of his career playing honourable heroes. He is one of those actors that has built an onscreen image for playing likeable heroes with courage. His good looks, charisma and larger-than-life presence have made him an ideal actor for playing classic American heroes. However, “Django Unchained” marked the actor’s first ever villainous role. As Calvin Candie, DiCaprio gives one of his most surprising performances. Out of all the characters that the actor has played throughout his career, Calvin Candie may be the most unlikeable. He’s a despicable slavery owner treating people with cruelty without any humanity. DiCaprio pours his heart and soul into the role, capturing the mischievous personality of a slavery owner whose emotions are out of control. Although he’s not the leading actor of the movie, DiCaprio steals every scene he’s in with his commanding personality. His strong commitment to the role is evident in the scene where DiCaprio actually injured his hand with a hammer while filming. It’s an extraordinary performance from an actor that thrives when he’s given opportunities to step out of his comfort zone playing characters with villainous personalities.

3. Inception

Not many directors in Hollywood have achieved appreciation of Christopher Nolan. With their non-linear stories, compelling characters and thought-provoking themes, Nolan’s movies have earned a huge following. “Inception” is a groundbreaking film that marked Leonardo DiCaprio’s first ever collaboration with Nolan. Headlining his first ever science-fiction blockbuster, DiCaprio showcased his strength as an actor. In one of the most complex roles of his career, DiCaprio captures the burden that guilt-ridden men bear. As Cobb, DiCaprio brought out an emotional and vulnerable side to his acting that audiences hadn’t seen before. Whether he’s mourning the loss of his wife or questioning whether he’s in a dream, DiCaprio effectively uses his expressions to capture the emotions of a man in a stressful situation. It’s a multidimensional role that gives the actor the opportunity to showcase his aptitude for playing complex characters whose motives are a mystery. A dream come true, it’s an extraordinary performance from one of the world’s greatest actors that hasn’t lost his ability to captivate by making movies which audiences value.

4. Catch Me if You Can

When it comes to the most clever con-artists that committed crimes on a huge scale, it’s worth discussing Frank Abagnale. During the 1970’s, Abagnale was a con-artist that committed shocking felonies. Whether it’s doctors, airline pilots or high school teachers, Abagnale impersonated multiple professions committing shocking cons. Eventually, he was caught by the FBI for crimes that couldn’t be hidden from the public eye. In 2002, Leonardo DiCaprio did an extraordinary job of portraying the con-artist in the film “Catch Me if You Can”. In the most charismatic performance of his career, DiCaprio excels at portraying a real-life con-artist that committed crimes without fear. It’s a role allowing the actor to capitalize on strengths at playing charming characters that are driven to achieve a goal. DiCaprio commands every scene showcasing charisma on the big-screen. In a career packed with performances that are celebrated, it stands out as the actor’s most underrated work. Nearly 40 years after a con-artist committed crimes that FBI rarely detected, it’s a captivating reminder of an actor whose timeless movies deserve to be celebrated.

5. The Departed

Few filmmakers that DiCaprio has collaborated with are as beloved as Martin Scorsese. Ever since 2002’s “Gangs of New York”, DiCaprio has collaborated with the world-famous filmmaker in six unforgettable movies. I adore all the movies that DiCaprio has made with Scorsese. However, my favourite collaboration remains “The Departed”. Released in 2006, Martin Scorsese’s Oscar-winning movie found the actor playing an undercover cop under intense anxiety. It was the first time DiCaprio stepped out of his comfort zone as an actor known for heartthrob heroes to play a conflicted character with complicated emotions. As Billy Costigan Jr., DiCaprio showcased vulnerability audiences hadn’t seen from the actor before. Intense, gritty and emotional, this was the actor giving a performance audiences had never seen before. “The Departed” marked a turning point in DiCaprio’s career when he went from being a heartthrob to a serious actor. It was the first of one of his many collaborations with Martin Scorsese that resulted in memorable movies. Nearly 20 years after the release of a celebrated film about undercover cops whose souls are departed, it’s a riveting reminder of an actor that thrives when given chances to play complex characters that are conflicted.

6. The Aviator

OCD is a debilitating disease rarely depicted accurately in movies. Hollywood has struggled to depict a complex mental condition that’s commonly misunderstood. As someone that suffers from OCD, I believe movies have rarely depicted the disease with authenticity. That being said, “The Aviator” is an exception. Released in 2004, Martin Scorsese’ movie did an extraordinary job of depicting an illness that had rarely been seen on the big-screen before. At the centre of it all is a fantastic performance by Leonardo DiCaprio, who captures the larger-than-life personality of a real-life aviator that achieved soaring success years ago. Not only does DiCaprio capture Howard Hughes’ charisma, but he embodies symptoms of OCD rarely depicted in Cinema. DiCaprio immerses himself into the role of an aviator with OCD whose life spun out of control. A powerful portrait of mental illness causing lives of aviators to deteriorate, it’s a captivating reminder of an actor that hasn’t lost his abilities to captivate whose timeless movies audiences will forever celebrate.

7. The Revenant

It isn’t easy to make an effective movie about survival. Making movies about individuals surviving catastrophes can often pose challenges for actors that are physically demanding. Actors are often required to show commitment to create engaging entertainment. In 2015, Leonardo DiCaprio proved he had this strong commitment when he made the “The Revenant”. Alejandro G. Innaritu’s movie found the actor pushing his body to the limit in his most challenging role. In the role for which he finally won an overdue Oscar, DiCaprio pours his soul into capturing the life of a fur trapper with a survival goal. Almost unrecognizable, he completely sheds his movie-star image to play an ordinary man with an extraordinary will for survival. It’s a physically demanding role most actors wouldn’t be able to pull off, but DiCaprio succeeds. As strong as Hugh Glass’ desire for survival, it’s a powerful reminder of an actor that thrives when he steps out of comfort zones to portray vulnerable characters overcoming obstacles that are painful.

8. Titanic

Few events in the history of mankind are as tragic as the sinking of the Titanic. During the 19th Century, the Titanic was a historic vessel that struck an iceberg sinking in a catastrophic shipwreck. A well-known disaster that changed the world forever, the sinking has often been depicted in popular culture. In 1997, Leonardo DiCaprio brought the tragic shipwreck to the big-screen in his iconic film “Titanic”. In the role that launched his career, DiCaprio embodied a lover engaging in a romantic affair on a ship destined to face despair. As Jack Dawson, DiCaprio created one of the most iconic romantic heroes in cinematic history. It’s a larger-than-life character that established the actor’s strength at playing heartthrob heroes. Nearly 90 years following tragic sinking of the Titanic, it’s a terrific reminder of an actor that has built a long-lasting legacy by playing empathetic characters facing catastrophic disasters in movies which are iconic.

9. Once Upon a Time in Hollywood

Mental health struggles faced by actors in Hollywood are rarely addressed in movies. Being an actor is a stressful profession that puts a strain on mental health. Actors face tensions of long working hours, high expectations and little breaks. Few movies I’ve seen have captured struggles faced by actors in Hollywood as powerfully as “Once Upon a Time in Hollywood. Released in 2019, Quentin Tarantino’s movie offers a powerful tribute to actors in 1960’s Los Angeles. In the most personal role of his career, DiCaprio captures the burden movie-stars in Hollywood bear. Drawing from his own personal experience, DiCaprio captures tensions actors in 1960’s Los Angeles were facing. It’s the most honest, emotional and vulnerable performance that the actor has ever given. A passionate tribute to the city of L.A., it’s a captivating reminder of an actor that thrives given opportunities to play compelling characters that has built a lasting legacy today.

10. What’s Eating Gilbert Grape

Autism is a complex disability rarely depicted in movies respectfully. Hollywood has often struggled to tell stories about disabled individuals with authenticity. As someone that suffers from Autism, I believe movies about the condition are rarely true to reality. However, “What’s Eating Gilbert Grape” stands out as an exception. Released in 1993, Lasse Hallstrom’s movie painted a powerful portrait of the intellectual disability. In one of his first ever roles, a young DiCaprio does an extraordinary job of portraying a child with Autism. From engaging in repetitive behaviours to lacking understanding of emotions, DiCaprio does an excellent job capturing a complex disorder. It’s a beautiful performance that set the stage for the star DiCaprio has become today. As strong as Gilbert Grape’s bond with his brother, it’s a breathtaking reminder of an actor with capabilities to portray compelling characters whose movies I will forever treasure.