The first rule of assessing Brad Pitt’s career is you must not dismiss him as a pretty boy actor. The second rule of assessing Brad Pitt’s career is you MUST NOT dismiss him as a pretty boy actor. When anyone is hand-picked by The Coen Brothers, Steven Soderbergh, David Fincher, Terry Gilliam, Quentin Tarantino and Terrence Malick, their place in cinema history is more than deserved.
So without further ado, and in no particular order: the greatest roles of Brad Pitt’s career.
Det. David Mills (Seven, 1995)
In the first of three David Fincher partnerships, Pitt effortlessly nails a helpless blend of naivety and hope. Without the heart invested in Mills and Tracy, in the very few scenes they share, the ending would be bereft of its knock-out power. A power that means Seven, and Pitt’s role in it, will be “puzzled over, studied and followed…forever”.
Floyd (True Romance, 1993)
Cinema has a healthy obsession with the herb but an unhealthy way of portraying smokers as active, adventurous, go-getters. Well not Floyd. Reluctant to ever leave the combo of TV and couch, even with a shotgun in his face, Floyd is the truest incarnation of a real cannabis fiend. Pitt has, in the past, often gone on record as saying he enjoyed a frequent toke himself. Method.
Jesse James (The Assassination of Jesse James by the Coward Robert Ford, 2007)
It’s a little hard for non-Yanks to comprehend just how iconic Jesse James is on the other side of the pond. It’s harder still to think of anyone being able to encapsulate the role in the manner that Pitt does. Half untouchable legend, half uncontrollable lunatic, Pitt’s James is a terrifying portrayal of a loved man lost.
Early Grace (Kalifornia, 1993)
It was a minor role in Thelma and Louise that catapulted Mr. Pitt to the winner of ‘gusset wetter of the 90’s’, but women really go moist for a true bad guy. And you don’t get much badder or guyer than playing a serial killer scaring every shade of shite out of Fox Mulder and that freaky sex woman from True Blood. The red on Early’s neck is all claret.
Mickey O’Neil (Snatch, 2000)
Taking time out from leading romantic man duties in Meet Joe Black and The Mexican, the Springfieldian journeyed over the pond after personally asking Guy Ritchie for a role in his Lock, Stock follow-up. The role, an indecipherable pikey with a mean right hook and a lot more behind the eyes than on display. Altogether now, “I need to have a shite”.
Chad Feldheimer (Burn After Reading, 2008 )
In a film full of more stupid people than a Jedward family reunion, Pitt’s Chad Feldheimer takes the stupid cake. His fate may be the cruellest, and least deserved, of any Coen character. The simplest of simple men that would be happy with a running machine, some headphones and a Schwinn. You think it’s a Schwinn.
Benjamin Button (The Curious Case of Benjamin Button, 2008)
Wrongly believed to be a tiresome, boring film by foolish fools Benjamin Button is, in actuality, a masterpiece of production, visual effects and subtle performances. Front and centre is Brad earning his second Oscar nomination as the young eyes looking out of an old body and vice versa. Like that film with Judge Reinhold and Fred Savage. What was that called?
Lt. Aldo Raine (Inglorious Basterds, 2009)
At inflicting ‘double leggers’ (laughter so hard the bottom half of your body flies upward), Pitt has caused a few. His finest appears in Tarantino’s latest as the Nazi-hunting Raine. After two hours of near flawless accents, and the unbelievably talented Christopher Waltz speaking in every dialect from Babylon, when Pitt and his cohorts say they’re going to pass themselves off as Italians, you don’t think twice that yet more perfect pronunciation is on its way. So when the worst Italian accent since Bob Hoskin’s Cockney Super Mario flows from Pitt’s mouth, in the finest deadpan delivery imaginable, it’s all you can do to hold onto your lower appendages.
Jeffrey Goines (12 Monkeys, 1995)
One mark of a fine actor is bringing to the table a performance exactly in keeping with the tone of the film. Pitt’s turn as the ludicrously named Jeffrey Goines (no wonder he was pissed with Daddy) is perfect Terry Gilliam. Twitchy, neurotic, funny but all the while batshit crazy, and opposite a never more subdued Bruce Willis, Pitt is exactly what the film needs. His first Oscar nomination richly deserved.
Tyler Durden (Fight Club, 1999)
We said earlier this is in no particular order but, yes, Tyler Durden is the best of Brad Pitt. When one of Hollywood’s biggest stars delivers a speech intoning that we “won’t all grow up to be movie stars” it takes more than a while to see the irony. Because Pitt is Tyler Durden. He looks like you wanna look. Fucks like you wanna fuck. And most of all he is free in all the ways you’re not. We can see why he has his haters, but with performances this strong, we’ve got nothing but love.