Holy Pitt! 7 Most Unforgettable Brad Pitt Roles

I was first exposed to Brad Pitt’s acting when he played rookie detective Mills in David Fincher’s Se7en. Slightly scrawny, an angry young man, all set to take up the world with his bare hands. Quite the contrast to the wise veteran, Somerset (Morgan Freeman), with whom he is partnered, yet his presence is undeniable.

Since then, I have been quite an ardent fan of his work, be it his acting or the films that he produces through Plan B Entertainment, a film and television production company that he co-founded with Jennifer Aniston and Kristin Hahn.

In his four-decade-long career, Pitt has proved himself to be worthy of all the praise of his versatile roles and natural chemistry with co-stars in films such as Once Upon a Time in Hollywood, The Curious Case of Benjamin Button, and Thelma & Louise.

In this article, we’re listing the most memorable performances by Brad Pitt.

7 Best Brad Pitt Movies

1. Thelma & Louise (1991)

Ridley Scott’s Thelma & Louise gave Pitt his much-awaited breakthrough in Hollywood, after his uncredited roles in films such as No Way Out, Less Than Zero, and No Man’s Land. Pitt played J.D. in Scott’s film about two female best friends who run away from their regular life for a road trip over the weekend and end up in trouble. Pitt’s J.D. is a charmer, and he knows it. He is a sharp contrast to the multitude of men whom the two titular characters come across on their adventure. Drop-dead gorgeous and a sweet talker, yet J.D. is no piece of meat thrown at Thelma, but rather a happy (and super sexy) memory that Thelma will look back at, years later. Or you could call him Thelma's lifetime regret because he did steal all of their money!

Despite his limited screentime, not only does Pitt add a layer of adventure to the narrative, but he owns the screen as much as the lead characters, lingering in your mind long after the credits roll.

2. Fight Club (1991)

Tyler Durden is everything that anyone would want to be—confident, superbly detached, and absolutely fearless. The leader of delinquents, Durden, is unapologetically faulty, and Pitt’s portrayal of him is raw and intense.

Ripped abs, dimpled cheeks, sarcastic side smile with fight scars all over his face, and a bizarre thirst for blood and destruction, Durden embodies the extremes of our emotions, and Pitt portrays it by reciprocating the same vigour, turning him into one of the most memorable antagonists in the history of cinema. Last but not least, Pitt’s chemistry with Edward Norton, as a fragment of Norton’s character’s schizophrenic hallucination, is pure perfection!

3. Inglourious Basterds (2009)

I’m going to finally say it out loud—Brad Pitt in a sleek moustache was a gift to us from Quentin Tarantino. A story of revenge against the Nazis, Pitt’s Lt. Aldo Raine is charming and gritty at the same time. Quick on his feet, darkly humorous, and sassy, Raine is a ruthless yet charismatic leader as he leads the “basterds” in his methods and ideology. A flat character, who remains steadfast in his ways, Raine undergoes little to no transformation throughout the narrative, yet Pitt’s portrayal of him feels ever-evolving. Raine is a slice of wonder, and Pitt simply owns the screen as Lt. Aldo.

4. Killing Them Softly (2012)

An underrated gem directed by Andrew Dominik, Killing Them Softly features Pitt as Jackie Cogan, a professional hitman with a bizarre ethos for non-violence. Despite being a professional killer, he preys from a distance and resorts to quick and painless methods, ensuring his targets die without any suffering.

Pitt’s Cogan doesn’t talk much or express with loud gestures (probably will blend into a crowd at his will), but his actions speak louder than his words. Pitt humanizes Cogan by exploring his deep-rooted fear of catching emotions through his performance, revealing both Cogan’s buried empathetic side and ruthless efficiency.

5. Moneyball (2011)

Bennett Miller’s Moneyball features Pitt in the lead role: Oakland A’s general manager Billy Beane, who sets out to assemble a baseball team based on a computer-generated analysis. Billy is determined and pragmatic with a competitive spirit that resides deep within.

Pitt’s portrayal of Beane is deeply human, blending frustration, hope, and intellect, beautifully bringing to life a man who is grappling with personal and professional challenges while trying to seek solace in pioneering a radical change in the sport that he loves.

From his idiosyncrasies to his leadership to his vulnerabilities, Pitt embodies Billy like an alter ego!

6. Once Upon A Time in Hollywood (2019)

Set in the ‘60s, Quentin Tarantino’s Once Upon a Time in Hollywood follows two men, Rick Dalton (Leonardo DiCaprio) and his stunt double Cliff Booth (Brad Pitt), who are desperately trying to recapture their lost days of glory. Pitt as Cliff is a laidback, charming, and enigmatic stuntman whose character arc revolves around his complex personal history and steadfast friendship with Rick.

With a background as a World War II veteran and former Green Beret, Cliff’s reputation is clouded by rumours. Pitt’s portrayal of Booth emphasizes his confidence and understated heroism while highlighting his struggle with becoming irrelevant.

7. Ocean’s Eleven (2001)

Pitt as Robert “Rusty” Ryan is the cool, highly skilled right-hand man and partner-in-crime to Danny Ocean (George Clooney) and is an integral part in planning and executing the heist that Ocean is staging to win back his ex-wife (Julia Roberts).

Pitt turns on his charms on the highest levels, showcasing effortless confidence and wit while adding humor and a sense of cool nonchalance, turning the character not only memorable but also extremely influential. I mean, who wouldn’t want to be Rusty?

These are just a few in his long filmography. Let us know if you’d like part 2!