Brad Pitt and Leonardo DiCaprio are both regarded by many as the best actor of today, and they’ve both been slaying Hollywood for decades. These two handsome, talented, and versatile actors are no newbies to the Academy Awards and the Golden Globes. Fans also really love to discuss which of these leading men is their favorite.

While fans finally got to see them on the big screen together for Once Upon a Time… in Hollywood, this only fueled debates over which of these guys is the best actor of the current generation. So, it’s time to pit them against each other – and see what their award-nominated roles have to say for their talent.

Brad Pitt: The Curious Case Of Benjamin Button (2008)

Brad Pitt and Cate Blanchett are basically everything all movie fans ever need. That, and a movie directed by David Fincher. The Curious Case of Benjamin Button is a fantasy drama that follows a man who appears to be aging backward.

With three Oscar wins and a whopping ten other nominations, Brad Pitt was the recipient of one of these nominations. This 2008 flick is the epitome of a stellar Oscar performance.

Leonardo DiCaprio: The Revenant (2015)

Leonardo DiCaprio finally took home his one and only Oscar for his role in The Revenant. Taking place in the 1820s, he plays a frontiersman who survives a bear attack but must also survive the terrain.

This riveting and entertaining flick took home three Oscars, and finally allowed fans to celebrate Leonardo DiCaprio the way this talented actor deserves to be celebrated – and his thrilling performance undoubtedly deserved it.

Brad Pitt: Twelve Monkeys (1995)

This actor is in hit after hit in the 2000s and 2010s, but fans should never forget his incredible work during the 1990s. Twelve Monkeys is one of them, and Pitt scored an Oscar nomination for this sci-fi thriller with Bruce Willis.

In a futuristic world, a convict is sent back in time to find out about the virus that has destroyed the world. This is another underrated flick that, thankfully, still saw all the talent that Pitt offered to his role.

Leonardo DiCaprio: Blood Diamond (2006)

This adventure thriller follows a fisherman, a smuggler, and a group of businessmen – all set out to find a diamond in the jungle. Leonardo DiCaprio’s performance was responsible for one of the five Oscar nominations that Blood Diamond received.

This film proves that there’s really nothing that Leonardo DiCaprio can’t do, and this riveting drama is only one of many roles that deserve serious recognition. It’s all about greed and determination and is DiCaprio in a raw performance with an intriguing character.

Brad Pitt: Moneyball (2011)

Brad Pitt scored a Golden Globe nomination for this biographical sports drama. Moneyball stars Pitt as Billy Beane, general manager of the Oakland A’s, and he tries to assemble an all-star roster with a tight budget and new computer software.

Alongside Jonah Hill and Robin Wright, this is undoubtedly one of Brad Pitt’s best performances of the decade. He didn’t make it to the Oscars, but at least the Golden Globes recognized him.

Leonardo DiCaprio: The Wolf Of Wall Street (2013)

There might not be a character on this list as iconic as Leonardo DiCaprio’s Jordan Belfort. Directed by Martin Scorsese, The Wolf of Wall Street is a biography crime drama unlike anything else that exists in Hollywood today.

Jonah Hill teams up with DiCaprio this time, as do Margot Robbie and Matthew McConaughey. DiCaprio’s captivating performance was one of the most talked about things that year, yet he didn’t win an Oscar. Still, this movie might just be one of the best of the 2010s.

Brad Pitt: Legends Of The Fall (1994)

It’s time to throw it back to the ’90s again and celebrate this Golden Globe nomination for Brad Pitt and his role of Tristan. Starring with the legendary Anthony Hopkins and Aidan Quinn, Legends Of The Fall is a war drama taking place in the 1990s.

With themes of betrayal, family, love, and war, this is a hidden gem of a performance that all fans of Brad Pitt must see. It’s not Fight Club, but it’s a ’90s throwback everyone needs.

Leonardo DiCaprio: The Aviator (2004)

This is a raw and refreshing role of DiCaprio’s, and this time, Cate Blanchett teams up with this legendary actor, as does Kate Beckinsale. His Oscar-nominated performance is as fantastic as any other.

Brad Pitt: Once Upon A Time… In Hollywood (2019)

Brad Pitt finally got the recognition he deserved and took home his first Oscar for acting for his flawless portrayal of Cliff Booth, a stunt man for a fading actor in 1969 Los Angeles.

Pitt is usually the leading man, but he’s also had some pretty outrageous and comedic roles – and this one is a perfect mixture of both. He’s sarcastic, hot-headed, hilarious, and totally mesmerizing. Brad Pitt in an orange floral shirt is all fans never knew they needed, and he crushed every second of this role.

Leonardo DiCaprio: Once Upon A Time… In Hollywood (2019)

Comparing DiCaprio’s and Pitt’s performances in this Quentin Tarantino flick is like comparing apples to oranges. They’re so different but both phenomenal. DiCaprio is Rick Dalton, a movie star that’s quickly losing his fame.

He’s needy, compulsive, and super down on himself, and his relationship with Brad Pitt’s character is wholesome and spectacular. This arrogant, lonely, and pitiful character is a fresh take for DiCaprio, and he certainly deserved his Oscar nomination for it.