My Favourite Leonardo DiCaprio Films of All-Time

Not many actors that achieved fame years ago are as beloved as Leonardo DiCaprio. Since the 1990’s, DiCaprio has become an icon. Whether it’s star-crossed lovers, corrupt stockbrokers or fur traders, DiCaprio has played many strong characters. Given the number of movies he has made, making a top 10 list isn’t easy. Nevertheless, listed below are my picks for the best movies of an actor that deserves to be celebrated.

1. The Wolf of Wall Street

Wall Street stockbrokers experiencing criminal behaviour have always fascinated my father. At an early age, I formed bonds with a father that appreciated lives of stockbrokers causing damage. A banker by profession, my father always took keen interest in stockbrokers orchestrating an organization. He would admire the way dark stockbrokers got away with committing crimes without facing a price to pay. Few films I’ve ever seen have captured the grim lives of stockbrokers on Wall Street as powerfully as “The Wolf of Wall Street”. Released in 2013, Leonardo DiCaprio’s best movie captured a stockbroker that committed serious felonies. In the greatest role of his career, DiCaprio embodies a Wall Street stockbroker that engages in a criminal lifestyle which becomes a burden to bear. This is the actor unlike you’ve ever seen him before: intense, charismatic and emotional in his most memorable role. DiCaprio has spent most of his career playing serious characters in intense dramas. With “The Wolf of Wall Street”, however, the actor showcased comedic timing that audiences hadn’t seen before. Working alongside Margot Robbie who is also amazing, DiCaprio honoured a legendary stockbroker in American history. For instance, the scene in which Jordan Belfort attempts to make his way to his Lamborghini in a state of drugs facing despair is one of the greatest moments of the actor’s career. Ultimately, what makes “The Wolf of Wall Street” Leonardo DiCaprio’s best movie is its message. Unlike most movies about Wall Street, it tackles universal themes that everyone would relate to. It delivers a strong message about crime which would resonate with everyone. Nearly 30 years after Jordan Belfort committed serious crimes on Wall Street, it’s a bold reminder of an actor that been hard to beat making great movies which audiences consider to be a treat.

2. Django Unchained

Slavery is a sensitive subject that always earned my friend’s respect. During my childhood, I formed a friendship with a kid in school that took great interest in slavery. He often made efforts to educate classmates on a past time in history about which he was passionate. As someone treasuring joyous memories of a companion that loved stories about slaves unchained, I adored “Django Unchained”. Released in 2012, Leonardo DiCaprio’s movie captured the harsh realities of slavery in American history. In the most villainous role of his career, DiCaprio embodied a sadistic slave owner that evokes fear. With “Django Unchained”, DiCaprio took a huge step out of his comfort zone to showcase a villainous side to himself that audiences hadn’t seen before. Working alongside Jamie Foxx who is also amazing, DiCaprio created a slave owner that’s compelling. For instance, the scene in which Candie smashes his hand on the dinner table threatening to murder Django’s wife causing fear is one of the greatest moments of the actor’s career. Ultimately, what makes “Django Unchained” a masterpiece is its message. The film delivers a strong message about slavery which would resonate with everyone. A bold portrait of slaves in history that are unchained, it’s a strong reminder about an actor that gained a following making movies that have entertained.

3. The Departed

Trusting people is something that I’ve always found difficulty doing. Years ago, my family faced grief when we discovered our housekeeper was a thief. I remember a housekeeper that treated my family nicely in a generous manner. My grandparents were shocked when they found their housekeeper they trusted had stolen jewelry. As someone that has often found people hard to be trusted, I loved “The Departed”. Released in 2006, Leonardo DiCaprio’s movie captured the lives of cops that are hard to be trusted. In the most conflicted role of his career, DiCaprio embodies an undercover cop that commits crimes causing despair. DiCaprio has an aptitude for conveying strong emotions through his expressions, and “The Departed” showcased his strengths. Working alongside Jack Nicholson who is also amazing, DiCaprio created a cop that’s compelling. For instance, the scene in which Billy Costigan uncovers the truth about Sullivan being an undercover cop causing despair is one of the greatest moments of the actor’s career. Ultimately, what makes “The Departed” a great movie is its message. The film delivers a bold message about trust which would resonate with everyone. A dazzling depiction of departed cops that are hard to be trusted, it’s a riveting reminder of an actor that has made timeless movies which deserve to be appreciated.

4. Inception

Dreams always fascinated my mother. At an early age, I formed bonds with a mother that was fascinated with dreams causing damage. She would love sharing her dreams with my family which she remembered clearly. Her dreams were often positive events that she would love to recall. Few films I’ve ever seen have captured dreams as powerfully as “Inception”. Released in 2010, Leonardo DiCaprio’s movie captured the lives of thieves infiltrating dreams causing catastrophe. In the most thought-provoking role of his career, DiCaprio embodies a thief that infiltrates dreams haunted by the death of his wife causing despair. DiCaprio has spent most of his career playing strong heroes that keep emotions bottled up. With “Inception”, however, he showcased vulnerability he hadn’t shown before. For instance, the scene in which Cobb is haunted by visions of Mal in his dreams causing despair is one of the greatest moments of the actor’s career. Ultimately, what makes “Inception” a masterpiece is its message. The film delivers a profound message about dreams which would resonate with everyone. As strong as Cobb’s desire to make his dreams come true, it’s a breathtaking reminder of an actor that has made timeless movies audiences value.

5. Titanic

The Titanic is a tragic shipwreck disaster that always fascinated my brother. I remember a brother that was fascinated by the shipwreck disaster. At an early age, I bonded with a brother that had immense knowledge about shipwreck damage. He was interested in becoming educated about a disaster he appreciated. In 1997, Leonardo DiCaprio honoured the tragic shipwreck in his film “Titanic”. In the most iconic role of his career, DiCaprio embodied an artist that engages in a romantic affair aboard a ship facing despair. DiCaprio has an aptitude for conveying emotion through monologues, and “Titanic” showcased his strengths as an actor. Working alongside Kate Winslet who is also amazing, DiCaprio honoured a historic shipwreck that’s frightening. For instance, the scene in which Jack and Rose bond together unaware that the ship they are on will sink is one of the greatest moments of the actor’s career. Ultimately, what makes “Titanic” a timeless classic is its message. The film delivers a meaningful message about disasters which would resonate with everyone. Centuries following the catastrophic sinking of the Titanic, its a breathtaking reminder of an actor that has manufactured commemorated movies which are iconic.

6. What’s Eating Gilbert Grape

Autism impacted my identity. At an early age, my life forever changed when I was diagnosed with Autism causing damage. The disorder affected my relationship with family under pressure. Few films I’ve seen have captured a disorder that’s hard to escape as powerfully as “What’s Eating Gilbert Grape”. Released in 1993, Leonardo DiCaprio’s movie captured Autism accurately. In the most physical role of his career, DiCaprio embodies an Autistic child causing his family to face despair. It gave the actor a chance to showcase emotional range he hadn’t shown in his career before. Working alongside Johnny Depp who is also amazing, DiCaprio created a portrait of Autism that’s compelling. An astonishing depiction of Autism, it’s a breathtaking reminder of a commemorated actor that has made memorable movies achieving stardom.

7. The Revenant

Movies about survival have always resonated with me. At an early age, my life changed when my family survived bombings causing damage. I felt grateful for my family’s survival. As someone haunted by bombings my family survived through commitment, I admired “The Revenant”. Released in 2015, Leonardo DiCaprio’s Oscar-winning movie depicted a fur trader’s survival. In the most physically demanding role of his career, DiCaprio embodied a brave fur trader driven to survive disasters causing despair. Almost unrecognizable, Dicaprio shed his movie-star image to play a man seeking survival. It gave the actor a chance to showcase commitment he hadn’t shown in his career before. As strong as Hugh Glass’ desire for survival, it’s a remarkable reminder of an actor whose timeless films audiences consider special.

8. Once Upon a Time in Hollywood

L.A. is a beautiful city that my grandfather loves dearly today. During my childhood, I bonded with a father that loved the city of Hollywood. He had dreams of one day visiting a city that shaped his life in a huge way. As someone treasuring a father that loved Hollywood, I adored “Once Upon a Time in Hollywood”. Released in 2019, Leonardo DiCaprio’s movie captured 1960’s Los Angeles. In the most personal role of his career, DiCaprio embodies a tormented actor carrying a burden to bear. It’s a role that gave the actor a chance to showcase his flair for playing conflicted characters. Working alongside Brad Pitt who is also amazing, DiCaprio created a movie-star that’s compelling. A beautiful tribute towards the city of L.A., it’s a breathtaking reminder of an actor that has made films which deserve to be celebrated today.

9. Catch Me if You Can

Few con-artists committing crimes that landed them in jail are as notorious as Frank Abagnale. During the 1960’s, Abagnale was a clever conman engaging in felonies. Abagnale participated in criminal activities until the day that he was caught by FBI authorities. In 2002, DiCaprio portrayed the notorious con-artist with a plan in his film “Catch Me if You Can”. In the most mischievous role of his career, DiCaprio embodied a notorious con-artist committing felonies causing despair. It’s a comical role that gave the actor a chance to showcase his aptitude for comedy. Working alongside Tom Hanks who is also amazing, DiCaprio honoured a con-artist. As memorable as crimes committed by Frank Abagnale, it’s a riveting reminder of an actor that has always made memorable movies with a strong drive to succeed rather than fail.

10. The Great Gatsby

Few books about millionaires have built a legacy as great as The Great Gatsby. Since its publication in 1925, Baz Luhrmann’s book has stood the test of time as a literary classic. In 2013, Leonardo DiCaprio did a great job adapting the book in his movie “The Great Gatsby”. In the most charismatic role of his career, DiCaprio embodies a mysterious millionaire that carries a burden to bear. DiCaprio brought his usual charisma to the role, standing out as the bright spot of a flawed movie. Although “The Great Gatsby” is far from a great movie, it celebrates DiCaprio’s lasting legacy. As strong as Gatsby’s desire to reunite with Daisy, it’s a riveting reminder of a commemorated actor that has built a lasting legacy producing memorable movies which I will forever treasure for inspiring me to turn dreams of film criticism into reality.