Leonardo DiCaprio turns 50! From heartthrob to Hollywood legend, here are some of his iconic roles

From a young, promising talent to an illustrious Oscar winner, his extraordinary journey has captivated audiences and critics alike for nearly three decades.
Leonardo DiCaprio then and now
Leonardo DiCaprio then and now
Updated on
4 min read

Today we celebrate a milestone in the life of one of Hollywood's modern legends—Leonardo DiCaprio turns 50! From a young, promising talent to an illustrious Oscar winner, his extraordinary journey has captivated audiences and critics alike for nearly three decades.

DiCaprio celebrated his birthday with loved ones during a party at his residence in Los Angeles on Saturday — two days before officially turning the golden jubilee age. The guest list was a star-studded one, ranging from Brad Pitt to Mark Ruffalo.

This took the internet by surprise as the list of invitees was rather 'age-appropriate,' given the actor is (in)famous for dating women under 25. According to Elle, DiCaprio is currently dating 26-year-old Italian model Vittoria Ceretti and the pair are still going strong!

Coming back to his profession, Leo has undoubtedly worked hard to reach the pinnacle of the industry. He's known for his dedication and commitment to challenging roles as exemplified by his performance in The Revenant when the actor ate raw bison, slept in an animal carcass and withstood freezing temperatures to portray the fur trapper Hugh Glass.

To mark this momentous occasion, let's revisit some of DiCaprio's most iconic roles en route to his recognition as one of Hollywood's brightest stars as well as finest actors.

What’s Eating Gilbert Grape (1993): At the age of just 19, DiCaprio received critical acclaim and his first Oscar and Golden Globe nominations for his performance as Arnie Grape, a developmentally disabled boy in this coming-of-age drama film. His portrayal was so authentic that you almost would have believed that the actor himself had this condition! Although he didn't win, this role was undoubtedly his breakthrough which earned him respect and high praise, especially for a newcomer. This performance also set the stage for an incredible career that would follow.

Titanic (1997): DiCaprio's career-defining role came with this American epic romantic disaster film where he played the ill-fated Jack Dawson, Kate Winslet's Rose's love interest. Directed by James Cameron, the film became a worldwide sensation, breaking box office records and winning 11 Academy Awards, including Best Picture. Titanic was a defining moment in both DiCaprio's career and Hollywood history. This iconic film holds a special place in pop culture with millions of fans still swooning over the 'King of the World.'

The Aviator (2004): In legendary director Martin Scorsese's epic biographical romantic drama DiCaprio portrayed Howard Hughes, the eccentric aviation pioneer with OCD. This film marked a major turning point in DiCaprio’s career, as he shed his heartthrob image and showed his depth as an actor capable of portraying complex, flawed characters. It also earned him a Golden Globe nomination for Best Actor thus cementing his status as a talented star.

Blood Diamond (2006): Directed and co-produced by Edward Zwick, this political war thriller is set during the Sierra Leone Civil War of 1991–2002, where DiCaprio plays Danny Archer, a diamond smuggler caught up in the war. He nailed a convincing South African accent and brought intense energy to the gritty role, showing his range and zeal for portraying difficult characters in complex stories. Once again he was nominated for both a Golden Globe and an Oscar, and while he did not win, his growth as a serious actor started gaining recognition.

Inception (2010): Filmmaker Christopher Nolan's 'Inception' was a high-concept sci-fi thriller that pushed DiCaprio's acting to new heights. His portrayal of Dom Cobb, a thief who steals secrets from dreams, proved his ability to handle emotionally layered roles. The film was both a commercial and critical success, making audiences rethink the very nature of reality. Additionally, it only highlighted the actor's versatility, further establishing him as one of Hollywood’s legends.

The Wolf of Wall Street (2013): Teaming up once again with Scorsese, DiCaprio delivered an explosive performance as the infamous stockbroker Jordan Belfort. With his manic energy, sharp wit, and an unrelenting charisma, our man Leo brought to life one of his most daring roles-- a morally corrupt character! His performance in this movie truly is unforgettable which is what made it a success.

The Revenant (2015): After years of near misses, Leo’s Oscar drought finally ended with The Revenant, directed by Alejandro G. Iñárritu. He took home the Academy Award for Best Actor for his gruelling role as frontiersman Hugh Glass. DiCaprio endured physical hardship and isolation for months to deliver one of his career's most intense performances. It was a just reward for his remarkable body of work which he had built over two decades, thus ending the internet’s running joke about his never-ending wait for the prized statuette.

Once Upon a Time in Hollywood (2019): Saving the best for the last, Leo teamed up with Quentin Tarantino to portray fading TV star Rick Dalton. His character as a struggling actor in 1960s Hollywood was equal parts funny, sad, and relatable. The film, set in 1969 Los Angeles, was an ode to Hollywood's golden age and DiCaprio's performance earned him another Oscar nomination. This role in particular allowed the actor to flex his comedic skills alongside his dramatic talents, proving that he could pull off both with equal flair.

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