Hollywood's famous hero Leonardo DiCaprio started acting in his teenage days. He always tries his best and portrays real feelings in every role. He can be funny, serious, kind, or even mean; basically, he can play any kind of person.
Over the years, Leonardo has been in many great movies and has done a wonderful job in all of them. But even though he was so good, he didn’t always win an Oscar. People think Leonardo should have won more than just one. Here are 10 Leonardo DiCaprio movies listed.
10 Leonardo DiCaprio movies that should’ve won an Oscar
What’s Eating Gilbert Grape (1993)

When to watch: Prime Video
Here he played a boy named Arnie who had a mental disability. 19-year-old, he acted so well that many people thought he really had the disability in real life. He made Arnie feel real, sweet, and full of energy. People were very touched by how honestly and deeply he played the role. Arnie is loved by the audience for being innocent, pure-hearted, and unpredictably joyful, bringing both laughter and emotion to every scene.
Despite his limitations, his character is emotionally honest and deeply loyal and serves as the emotional anchor that reveals the struggles and love within his family. Leonardo was even nominated for an Oscar, but he didn’t win. The award went to Tommy Lee Jones for The Fugitive.
Catch Me If You Can (2002)

When to watch: Prime Video
Here, as Frank Abagnale Jr., Leonardo tricked people by pretending to be a pilot, doctor, and lawyer. Before he turns 21, he does this in a very smart, funny, and interesting way. He worked closely with Tom Hanks in the movie, and they acted very well together. The movie was fun to watch, and Leonardo showed he could play a clever and sneaky character.
Frank Abagnale Jr. is liked by the audience for being charming, quick-witted, and fearlessly clever, making his cons thrilling yet oddly lovable. Beneath his confidence and humor lies a lonely, vulnerable, and deeply insecure young man who is simply trying to escape his pain and find a place to belong is very much acceptable to the audience, but he didn’t get an Oscar nomination for this role.
The Departed (2006)

When to watch: Prime Video
In this film, Leonardo played a police officer whose name is Billy Costigan. He had to pretend to be a criminal to catch a gang leader. This was very dangerous, and his character felt scared and stressed all the time. Billy Costigan is liked by the audience for being brave, intensely loyal, and morally conflicted, making his struggle feel raw and real.
His character has deep emotional layers; he is haunted, isolated, and constantly torn between duty and survival, showing the true cost of living a dangerous lie. The movie won the Oscar for Best Picture. Instead, he was nominated for Blood Diamond that same year. Many people thought this was unfair because his acting in The Departed was even better and should have been noticed.
Revolutionary Road (2008)

When to watch: Prime Video
Leonardo as Frank Wheeler surprises us in this movie, who lived with his wife in the suburbs. Even though they looked like a happy couple, they were really very unhappy inside. Frank didn’t like his job and wanted something more from life. Leonardo here showed the disappointment, anger, and confusion of someone who feels trapped.
His acting was full of real emotion, and many people believed in his character. But he did not get nominated for an Oscar for this role. This movie showed that Leonardo is also very good at playing regular people with real-life problems.
Shutter Island (2010)

When to watch: Prime Video
Leonardo played a police officer in this mystery movie. He went to a hospital for mentally ill patients to look for a missing person. As the story continued, Teddy started to get very confused and didn’t know what was real anymore.
Leonardo DiCaprio showed his character’s fear, sadness, and anger in a very strong way. His acting made people feel what Teddy was feeling, and the ending surprised many viewers. Even though the movie was popular among people, the actor did not get nominated for an Oscar.
Django Unchained (2012)

When to watch: Prime Video
A very mean man named Calvin Candie, Leonardo here, owned a big farm and treated people very badly. Leonardo did a great job showing how evil the character was. In one scene, Calvin hit a table so hard that he hurt his hand and started bleeding, but he didn’t stop acting.
He kept going with the scene. This scene showed how serious he was about doing a good performance. Even though he had strong and brave acting skills in this movie, he was not nominated for an Oscar.
The Wolf of Wall Street (2013)

When to watch: Prime Video
A man who got rich by lying and stealing money in the stock market can be a hero in a movie. Leonardo proves that. The movie had lots of crazy scenes, wild parties, and funny moments. Leonardo DiCaprio was full of energy and acted like a person who only cared about money and fun.
He made people laugh but also showed how bad things can happen when someone wants too much money. He was nominated for Best Actor for this movie, but instead of him, the Oscar went to Matthew McConaughey for Dallas Buyers Club.
Once Upon a Time in Hollywood (2019)

When to watch: Prime Video
Leonardo, as Rick Dalton, shows us that he keeps getting better as the years pass by. In this film, Rick was worried about his not-so-famous personality. He felt sad and scared about losing his job. In one scene, he just forgets his lines and gets mad at himself.
Hilariously, that scene was both funny and sad at the same time. Rick Dalton is liked by the audience for being relatable, insecure, and endearingly dramatic. Beneath his fading fame and loud emotions lies a fragile, hopeful, and deeply human soul, clinging to purpose in a changing world. He was nominated for an Oscar again for this role, but winning an award was not in his fate. Still, his acting steals the audience's heart.
Blood Diamond (2006)

When to watch: Prime Video
Leonardo plays a man named Danny Archer who lives in Africa and speaks an African language. At first, Danny only cares about money and wants to find a special diamond during a war. He speaks with an African accent in the movie. But as the story goes on, Danny starts to change. He begins to care about other people and not just himself.
Leonardo DiCaprio showed both the tough and the kind sides of Danny very well. Danny Archer is liked by the audience for being rugged, charismatic, and morally complex, keeping viewers intrigued by his transformation. Beneath his tough, selfish exterior, he reveals a conflicted, redeemable, and ultimately sacrificial man who learns the value of humanity in a world torn by greed and violence. Even after the nomination, Leonardo did not win the Oscar for this movie.
The Aviator (2004)

When to watch: Prime Video
He plays Howard Hughes, who loved building airplanes and making movies. On the other hand, Hughes also had a serious illness called OCD. This made him very worried about germs and made him want everything to be perfect always. What it's like to live with this kind of illness, Leonardo shows that.
He also showed how Howard was very smart and full of big dreams but also very sad and afraid. Even after a nomination for an Oscar, Leonardo got unlucky this time too.
In every movie, Leonardo DiCaprio gives his full effort and makes his character feel real. Even though he finally won an Oscar for The Revenant, many of his other roles were also very good and deserved to win. Movies like What’s Eating Gilbert Grape, The Aviator, Blood Diamond, and The Wolf of Wall Street show how great his acting really is. Winning awards is nice, but not winning doesn’t mean someone isn’t great. Leonardo has made many movies that people will always remember. Fans will keep watching and enjoying his work for many years to come.
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