Leonardo DiCaprio’s birthday: A look back at his 7 iconic Oscar nominations

Today, on November 11, we celebrate a true Hollywood legend’s milestone—Leonardo DiCaprio turns 50! DiCaprio has grown up right before our eyes, evolving from a heartthrob to a movie star with depth, an actor who seems just as comfortable snagging elusive Oscar nominations as he is making headlines for his (in)famous dating life with women under 25. But there’s no denying his genius on screen, nor the way he’s slowly but surely wormed his way into the Oscars’ good graces over the years. So, let’s dive into his seven Oscar-nominated roles, where he earned (and sometimes lost) the Academy’s recognition, taking him from a fresh-faced teen to one of the industry’s finest.

1. What’s Eating Gilbert Grape (1993) - Best supporting actor

DiCaprio’s first nomination came at just 19 years old, where he played Arnie Grape, the young brother of Gilbert (Johnny Depp) who has an intellectual disability. His portrayal was so authentic that many viewers thought DiCaprio himself had a similar condition—high praise, especially for a newcomer! While he didn’t win, his breakthrough role earned him instant respect and set the stage for the incredible career that would follow.

2. The Aviator (2004) - Best actor

Flash-forward a decade, and DiCaprio was no longer a newbie but a major Hollywood contender. In The Aviator, directed by Martin Scorsese, he took on the role of Howard Hughes, the eccentric aviation pioneer with OCD. DiCaprio’s performance was intense, raw, and meticulously crafted, but the win evaded him once more. This nomination, however, solidified his status as a serious actor and frequent Oscar nominee.

3. Blood Diamond (2006) - Best actor

Enter Blood Diamond, where DiCaprio played Danny Archer, a diamond smuggler caught up in the Sierra Leone Civil War. DiCaprio nailed a convincing South African accent and brought intense energy to the gritty role, showing his range and dedication to portraying difficult characters in complex stories. Yet again, no Oscar, but it only added to the narrative that DiCaprio was chasing something elusive.

4. The Wolf of Wall Street (2013) - Best actor

Ah, The Wolf of Wall Street—the movie that became an instant classic. Leo teamed up with his frequent collaborator Scorsese, taking on the role of Jordan Belfort, a party-loving, ethically questionable stockbroker. His wild, larger-than-life performance was pure DiCaprio gold. Who could forget that quaalude scene? While it didn’t bring him Oscar gold, it left an indelible mark on pop culture and once again proved his versatility.

5. The Revenant (2015) - Best actor (Winner)

After years of near misses, Leo’s Oscar drought finally ended with The Revenant, directed by Alejandro G. I?árritu. In this brutal survival story, DiCaprio portrayed Hugh Glass, a frontiersman who endures the harsh wilderness and a bear attack in his quest for revenge. Leo’s commitment was legendary—he ate raw bison liver, slept in animal carcasses, and battled freezing temperatures. His dedication was finally rewarded with his first Oscar win, ending the internet’s running joke about his never-ending wait.

6. Once Upon a Time in Hollywood (2019) - Best actor

Teaming up with Quentin Tarantino, DiCaprio’s role as Rick Dalton, a struggling actor in 1960s Hollywood, was equal parts funny, sad, and relatable. Dalton, a fading TV star worried about his career, gave Leo the chance to flex both his comedic and dramatic chops. Although he didn’t win, this performance reminded audiences why he’s considered one of the best of his generation.

7. The Wolf of Wall Street (2013) - Best picture (Producer)

Beyond acting, DiCaprio co-produced The Wolf of Wall Street, earning a nomination for Best Picture. Although it didn’t win, this nomination highlighted Leo’s skills as a producer and his dedication to pushing cinematic boundaries both in front of and behind the camera.

A journey through film and heart

So, what does Leo’s journey say about him as he celebrates this big 50 milestone? DiCaprio is more than a series of Oscar nods or headlines about his love life. He’s an actor who has pushed boundaries, taken on demanding roles, and devoted his life to his craft. From his raw portrayal of a vulnerable young boy in What’s Eating Gilbert Grape to a vengeful frontiersman in The Revenant, DiCaprio has cemented his place in cinematic history, one iconic role at a time.