Never Just a Pretty Face: Brad Pitt, Actor & Producer

Who ever thought Brad Pitt would one day get old? It just seemed inconceivable, even as his features have notably weathered over the years. Still, Once Upon a Time in Hollywood was really the first movie to not only acknowledge that Pitt is a guy in his mid-fifties, but to actively celebrate it. 

There was that moment when he hopped casually up onto a roof for some repairs and nonchalantly stripped off his shirt; in the screening I was in, the entire audience audibly gasped. I’m 14 years younger than Pitt and I instinctively sucked in my beer gut.

I like that scene because Pitt owned his age while still looking amazing, every inch the Hollywood icon. He won a Best Supporting Actor Oscar for that movie, which was fitting; although Pitt is perfectly capable of carrying a movie, many of his most interesting parts have come in supporting roles. That rooftop scene also offered a sly nod to his sex symbol status at the start of his career, something that he was never quite able to shake off.

1990s: Breakthrough, and subverting the heart-throb image

Pitt was shirtless in his breakthrough role, too. Before Thelma & Louise, he’d played a few bit parts, worked on TV, and starred in his first lead role, but it was Ridley Scott’s classic road movie that brought him to a wider audience. His contribution was a small but memorable one playing J.D., a charming young outlaw who woos, romances, and robs one of the on-the-lam friends. People are still writing about that role and its impact on masculinity 30 years later.

While his next two films, Johnny Suede and Cool World, were quickly forgotten, A River Runs Through It earned him the reputation as heir apparent to its director, Robert Redford.

If his early roles defined him as a Hollywood sex symbol, it was a label that Pitt was eager to toy with or shed completely even in the formative years of his stardom. He grunged up to play a redneck psycho in the serial killer movie Kalifornia, and had another scene-stealing part as Floyd, the perpetually stoned couch potato in True Romance. The latter role was more convincing, perhaps because Pitt has had a lifelong taste for ganja, which has sometimes had detrimental effects on his life and career.

Adding a little bad boy edge certainly helped temper the pretty boy stereotype, although his next two major roles leaned heavily into his heartthrob status again. He looked awkward in cravats and frilly shirt sleeves opposite an equally mis-cast Tom Cruise in Interview with the Vampire, but showing his genuine leading man credentials in Legends of the Fall.

1995 was the year that really sent Pitt’s career stratospheric. He was convincing as the hot-headed rookie detective who receives a very nasty surprise package in Seven, his fiery impatience neatly balanced by Morgan Freeman’s measured performance. The film was a massive hit and an instant pop culture moment, inspiring a whole slew of inferior grim, dimly-lit ripoffs and the “torture porn” subgenre.

On top of that huge commercial success, he also turned in an entertaining if gimmicky Oscar-nominated performance as a weirdo anti-capitalist radical in 12 Monkeys, which felt like a warm-up for his iconic role in Fight Club. Unfortunately for him, his onscreen Seven nemesis Kevin Spacey was also shit hot that year, beating Pitt to the Best Supporting Actor award for The Usual Suspects.

After that strong year, there were a string of mediocre films: Sleepers, The Devil’s Own, Seven Years in Tibet, and the yawn-inducing Meet Joe Black. This period is only really worth mentioning because it introduced another aspect of Pitt’s range: the dodgy accent. In Tibet he occasionally approximated an Austrian cadence, while his attempt at Northern Irish in The Devil’s Own was branded by the Belfast Telegraph as one of the worst in movie history.

Then came Fight Club, the movie that turned Pitt into a pin-up for boys as well as girls. Pitt’s natural cool helped him fully embody Tyler Durden, the nihilistic leader of anarchist group Project Mayhem and ringleader of an underground boxing circle where buttoned-up men like the narrator, Edward Norton, could get some catharsis from their milquetoast lives by beating each other to a pulp.

I’ve always had a bit of trouble swallowing the film’s anti-corporate call-to-arms, coming from one of Hollywood’s largest studios with a $60 million budget, but it was an iconic role for Pitt and his performance still plays well, even if Durden’s philosophising sounds more like an incel manifesto today.

2000s: Superstardom and Brangelina

His unforgettable turn as Tyler Durden meant Pitt entered the 21st century at peak cool, a status he would reinforce with another leftfield supporting role in Guy Ritchie’s Snatch, playing the unintelligible bare-knuckle boxer, Mickey “One-Punch” O’Neil. In a cast packed with memorable performances from the likes of Alan Ford, Jason Statham, and Frank from Eastenders, Pitt stole the show and gave the movie a little extra stardust.

Another easy-going turn as George Clooney’s ever-snacking sidekick in Ocean’s Eleven certainly didn’t hurt his cool credentials, nor did making cameo appearances on Friends with his then-current wife, Jennifer Aniston, or dressing up as a monkey for a Jackass skit.

Now reaching the height of his stardom, the next few years were some of his least interesting part-wise. He played Achilles in Wolfgang Petersen’s empty spectacle Troy, reprised his role in Ocean’s Twelve, and starred alongside his future spouse Angelina Jolie in the completely throwaway Mr. & Mrs. Smith. Rumors circulated that Pitt and Jolie were together before he divorced Anniston and “Brangelina” became a source of intense paparazzi scrutiny, although they wouldn’t actually marry until several years later.

The next few years saw Pitt entering a new phase in his career, producing as well as starring. He co-produced Martin Scorsese’s Oscar-winning triumph The Departed, and introspective roles in Babel and The Assassination of Jesse James by the Coward Robert Ford marked a new maturity to his acting.

Even so, it wasn’t all serious. There would still be plenty of fun stuff, like his hilarious supporting turn as an airheaded gym instructor in Burn After Reading and trying on a broad Texan accent for Inglourious Basterds. Although his entertaining part as a Nazi-scalping commando was only a supporting role, he was a massive presence in the marketing campaign for the movie. In between, he also found time to earn an Oscar nomination for Best Actor for The Curious Case of Benjamin Button.

Pitt continued to prove his comic chops with a good voice role in Megamind, and achieved further success as a producer with films like Kick-Ass 2 and Eat Pray Love, before another peak year in his career. 2011 saw him give arguably the best performance to date playing a strict father in Terence Malick’s wondrous The Tree of Life, and receiving another Best Actor Oscar nod as the straight-talking baseball coach who learns how to crunch the numbers in Moneyball. The former once again showed his maturity as an actor, creating a fully realised character amid Malick’s typically elliptical storytelling.

Over the past ten years or so, Pitt seems to have taken his foot off the gas as an actor, although he has been such a huge presence in movies for the past 30 years that it still feels like he’s never off our screens. He still makes films, doing solid leading man work in World War Z and Fury, starring opposite Angelina in her pet project By the Sea, playing part of an ensemble in The Big Short, and looking like he’s been time warped in to give an anti-slavery speech in 12 Years a Slave.

More and more, however, his focus has been producing films. A casual glance at the list reveals his good taste in projects and devotion to humanitarian and political causes, serving as Executive Producer on The Lost City of Z, Okja, Selma, and the Oscar-winning Moonlight, among many others.

Which brings us to 2019, and another good year with a heartfelt performance as an astronaut with daddy issues in Ad Astra and his Oscar-winning turn as laidback stunt double Cliff Booth in Once Upon a Time in Hollywood, the movie that sent a million men scrambling to renew their gym membership. 

Now, if you’ll excuse me, I need to do a little workout myself. If I get cracking now I might look like Brad Pitt by the time I hit my mid-fifties.

So there you have it, a brief rundown of Brad Pitt and his brilliant career. What are your favourite Pitt movies?