Thelma & Louise (1991)
The Role: J.D.
Why It’s The Best: It’s Pitt’s big break; one that he understandably had to fight for, but the raw performance he delivers is perfect for his character. Effortlessly appealing, he plays it like he’s a romcom love interest before pulling the rug out from under our (and Thelma’s) feet.
Iconic Moment: J.D. encounters Thelma's husband after being taken in for police questioning and taunts the man with a few thrusting hip motions.
Brad Says: “I believe they’d already been through one person and I got a reading for it. I picked up the script and I knew that this was one I’d love to get a hold of. So I read for that part, and then didn’t hear anything. I think a month went by.
And I got another call about a month later, apparently someone else had fallen through. I went and read with Geena. Ridley kept wanting to see the romantic scenes, and I kept wanting to do the Harvey Keitel scene to show the switch. He said, ‘No.’ He told me he wanted to see a real sociopath. I had to go look that up!”
Twelve Monkeys (1995)
The Role: Jeffrey Goines
Why It’s The Best: Pitt cuts loose as a total raving loon, and utterly convinces in the role (take that as a compliment, Brad!). Proving he knows when to play it big and when to rein it in, Pitt’s version of a mentally unstable inmate really is quite something.
Iconic Moment: Jeffrey befriends fellow patient James Cole, gives him the grand tour of the loony bin and just... won’t... stop... talking .
The Role: Detective David Mills
Why It’s The Best: It takes something special to play the good guy without becoming nothing more than a bland plot prop. But Pitt infuses his David with dark edges and charming naivety, ensuring that we’re never doing anything other than rooting for him as he tracks down a serial killer alongside Morgan Freeman.
Iconic Moment: That horrible ending, in which David discovers just how far serial killer John Doe will go in order to fulfil his terrible mission.
Brad Says: “Looove Seven . I had such a good time on that film. That was probably one I had the most fun on and the most sick one of them all, right? I had a gut feeling. Things were just falling into place; it just felt right.”
Fight Club (1999)
The Role: Tyler Durden
Why It’s The Best: Back with Fincher for a second time, Pitt’s as confident (and toned) as ever in a troubling, controversial mindfucker that has one of the coolest twists in cinema history.
Iconic Moment: “I want you to hit me as hard as you can,” Tyler tells The Narrator. “How much can you know about yourself if you’ve never been in a fight?”
Brad Says: “I was pretty excited about doing it. I hadn't read anything like it, and I read everything. It's an astounding, extraordinary, amazing movie. It's a pummelling of information. It's Mr. Fincher's opus. It's provocative, but thank God it's provocative. People are hungry for films like this, films that make them think.
“Fincher, Norton, and I had endless discussions about it before we started filming. We sat around for months battling around ideas, breaking apart every line like it was Shakespeare. It's such a hard film to get a handle on. How do you characterise something you've never seen before?
“Did you see the DVD that Fincher put out? He put all the negative reviews in the booklet. Some London critic said, ‘Not only is it anti-capitalistic, but it’s anti-society and anti-God.’ We were like, ‘We didn’t realise it was that good!’”
Burn After Reading (2008)
The Role: Chad Feldheimer
Why It’s The Best: Though better known as a dramatic actor, Pitt shows off his considerable skills as a comedian as he plays dopey gym worker Chad. Though it’s a larger-than-life role, Pitt never over eggs it, and we end up with something genuinely funny.
Iconic Moment: Chad gets surprised in the closet, and loses his head...
Brad Says: “I'm much more experienced now, so I can find films that are interesting quicker and cut out the films that don't really matter. It means more to me now because my kids are going to see them, and I want them to be proud.
“I guess I've been investing in American characters lately. I find America really, really interesting in this last decade. That's been my focus. As for comedies, I felt like I've been doing comedies for years. [ laughs ] Maybe they weren't so funny.”
The Assassination Of Jesse James By The Coward Robert Ford (2007)
The Role: Jesse James
Why It’s The Best: Pitt plays with James’ persona, crafting a tricky character who you’re never quite able to pin down. One minute he’s vulnerable, the next scarily capable. That Pitt manages to project so much with so few lines is the mark of his ever-burgeoning talent.
Iconic Moment: “You wanna be like me, or you wanna BE me?” James hits the nail on the head.
Brad Says: “It’s a much more intimate story; I seem to be drawn to those of late, and there’s this contemplative aspect to the story.
Also, it was working with Andrew Dominik and the fact that the story spoke a lot about fame and the quest for fame, without really understanding the consequences.
And the Jesse James character is both trapped behind a facade and caught at a crossroads – and please don’t draw any parallels, because I don’t feel like I’m trapped behind any facade. Though certainly the trappings of celebrity I understand.”
The Curious Case Of Benjamin Button (2008)
The Role: Benjamin Button
Why It’s The Best: It’s one of Pitt’s most challenging and varied roles as he plays a character through the various stages of his life, from wrinkled young child to youthful old man. He also had a host of other factors to contend with (including masses of CGI), but still manages to turn in an affecting performance as the afflicted Button.
Iconic Moment: Benjamin stands in front of the mirror, looking for all the world like an old man even though he’s barely into his teens.
Brad Says: “I find Benjamin is about those universal things we all share, that 95 percent that makes us all the same, wherever we are in the world. Our loves, our hopes, but also the loss that we all walk around with and hide very well, and the ultimate notion that we’re all expendable.
"To me, it’s a counterstatement to this divisive period we’ve been in, where we focused on the two, three, four, five percent of ways in which we’re different.”
The Role: Early Grayce
Why It’s The Best: It’s basically Pitt taking his character from Thelma & Louise and dialling him up to 11. Starting off as an easy-going charmer, a new side of Early quickly emerges as we begin to suspect that he’s hiding something of a dark past.
Iconic Moment: Early responds to all the screaming in his car by letting out a few howls of his own .
Brad Says: “I’m basically a guy who finds farts funny and things like that. My character’s a redneck. A real backwoods hillbilly, you know. He’s a guy with no morality. An idiot. He kills people as if they’re bugs.
“He hasn’t had many options, so he’s created his own ideas about right and wrong, and they’re a bit off from what other people think. He creates things in his life for excitement, and one of those things happens to be murder.”
A River Runs Through It (1992)
The Role: Paul Maclean
Why It’s The Best: Pitt gets to flex more subtle dramatic muscles, tugging at the heart strings as one of two brothers who do everything together. What could easily have become maudlin and hammy is deftly handled by Pitt and co-stars Tom Skerritt and Craig Sheffer, with whom our boy shares crackling chemistry.
Iconic Moment: Paul and his brother attempt to steer a rowboat through the rapids, dodging vicious rocks all the way down.
Brad Says: “I just remember that growing up, I couldn’t stand it if someone took advantage of [ my brother ] or was mean to him in any way. I just wanted to go and punch them in the throat. It drove me crazy and I couldn’t stand to see him get hurt.
“Then it came to a point where I realised I’d been through it and it had made me stronger, so I just had to sit back and let him go. He’ll figure it out, he’s a smart boy. So yeah, the brother thing struck a big chord with me and was very important to me.”
True Romance (1993)
The Role: Floyd
Why It’s The Best: He may spend pretty much every minute of the film’s running time lazing about on a couch, but Pitt handles it with so much conviction that it’s hard not to flag it up as one of his finest moments. Loading up never looked so cool. Or greasy.
Iconic Moment: Floyd gets an ammo-heavy visit from the mob, and just cracks the heck up . “Aw, man,” he sniggers.
Brad Says: “I’m a method actor.” [ We assume he’s joking ]