Top 10 Coolest Things About Brad Pitt

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Brad Pitt has built one of Hollywood’s most varied careers, jumping from daring character pieces to blockbuster ensembles while also shaping the industry behind the scenes as a producer. He’s collaborated with major directors, anchored award-winning films, and made memorable TV appearances that still get referenced today. Below are ten cool, fact-driven highlights—starting with movies and TV shows—showing how his work has left a serious mark on pop culture.

‘Once Upon a Time… in Hollywood’ (2019) – his first acting Oscar

Pitt won his first acting Academy Award for playing stuntman Cliff Booth in Quentin Tarantino’s film. The role also earned him major critics’ prizes across the globe. His awards sweep recognized both his performance and a career of standout supporting turns.

’12 Monkeys’ (1995) – the role that made awards bodies take notice

'Twelve Monkeys' (1995) - the role that made awards bodies take notice

His performance as Jeffrey Goines brought Pitt his first Oscar nomination and a Golden Globe win. The part showcased his ability to disappear into eccentric, high-energy characters. It also cemented him as more than a matinee idol by highlighting his range in psychological sci-fi.

‘Fight Club’ (1999) – a transformative collaboration with David Fincher

Pitt’s turn as Tyler Durden demanded extensive physical preparation and meticulous coordination in fight choreography. The film’s production paired him tightly with director David Fincher, beginning a creative partnership that fans and filmmakers still study. Its dialogue, visual style, and marketing became touchstones for late-era studio risk-taking.

‘Se7en’ (1995) – grit on screen and off

During production, Pitt injured his arm in a real accident, and the filmmakers incorporated the cast into the story rather than halt the shoot. The film marked one of his earliest intense collaborations with Fincher on a dark procedural that redefined the genre’s visual language. Its bleak finale and meticulous design influenced a wave of neo-noir thrillers.

‘Ocean’s Eleven’ (2001) – the coolest ensemble trick

As Rusty Ryan, Pitt is famously eating in scene after scene—a character choice that became an in-joke throughout the trilogy. The film’s success helped reboot the slick caper for modern audiences and launched two sequels. It also highlighted Pitt’s timing in ensemble settings alongside an A-list cast.

‘Inglourious Basterds’ (2009) – leading Tarantino’s breakout global hit

Pitt’s Lt. Aldo Raine fronted an ensemble that became Tarantino’s highest-grossing release at the time. The movie’s mix of multiple languages, chapter structure, and audacious set pieces broadened its international appeal. It also introduced wider audiences to several future stars through its festival buzz and awards run.

‘Moneyball’ (2011) – double recognition as actor and producer

Playing Billy Beane brought Pitt a Best Actor nomination while the film also received a Best Picture nod with him among the producers. The project helped popularize front-office analytics for mainstream audiences without sacrificing character depth. Its smart, dialogue-driven structure became a model for sports dramas focused on process over spectacle.

‘The Tree of Life’ (2011) – prestige cinema at its most ambitious

Pitt starred for Terrence Malick in a meditative family saga that won the top prize at Cannes. The film’s experimental structure blended intimate domestic scenes with cosmic imagery in a way few studio-backed projects attempt. His restrained, patriarchal performance anchored the movie’s emotional core.

‘Friends’ (1994–2004) – a guest spot that earned an Emmy nod

Pitt appeared in the episode widely known as “The One with the Rumor,” playing a former classmate with a very specific grudge. The cameo landed him a nomination for Outstanding Guest Actor in a Comedy Series. It remains one of the show’s most rewatched celebrity appearances.

Plan B Entertainment’s Best Picture wins

Beyond acting, Pitt co-founded Plan B Entertainment, the company behind multiple Best Picture Oscar winners: ‘The Departed’, ’12 Years a Slave’, and ‘Moonlight’. The banner has also championed distinctive auteurs and challenging subjects across film and television. This producing track record shows his long-term impact on the kinds of stories that get financed and celebrated.

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