The highs and lows of Brad Pitt

This December Brad Pitt will hit the grand old age of 59. Hard to believe, considering that he has retained much of his youthful appeal, despite a well-documented penchant for cigarettes, weed and booze, habits apparently now finally kicked to the kerb.

As he approaches his seventh decade, Pitt has discussed his desire to transition from acting to a production-focused role, which has already long been a feature of his career.

Pitt’s impressive production credits include many pictures where he didn’t appear onscreen, including Running with Scissors (2006), The Departed (2006), Kick-Ass (2010), Selma (2014), Moonlight (2016) and The King (2019). He has also branched out into television, executive producing an array of prestige projects such as The OA (Netflix, 2016-19), The Third Day (Sky Atlantic, 2020) and The Underground Railroad (Amazon Prime, 2021).

Pitt was 28 when he made it big, playing roguish drifter J.D. in Ridley Scott’s Thelma & Louise (1991). Starring roles followed thick and fast, with commercial fare (Legends of the Fall, The Devil’s Own) astutely balanced by more left field choices (Babel, The Tree of Life).

Of his own films, Pitt has said box office flop The Assassination of Jesse James by the Coward Robert Ford (2007) is his favourite.

Pitt played the titular gunslinger in a movie he stated was: 'a statement on celebrity and wanting to make a name for yourself without any substance under that. It’s a beautiful film. It really is. That was near and dear to me, as well as the ten other people who’ve seen it.'

The worst? The actor was unequivocal in naming 2004’s Troy, where he played Homeric hero Achilles: 'It’s no slight on Wolfgang Petersen. Das Boot is one of the all-time great films. But somewhere in it, Troy became a commercial kind of thing. Every shot was like, ‘Here’s the hero!’ There was no mystery.'

Pitt is not calling time on acting just yet though – fans can look forward to seeing the star in David Leitch’s (Atomic Blonde) upcoming action-comedy Bullet Train and as tragic silent star John Gilbert in Babylon, directed by Damien Chazelle (Whiplash).

Incidentally, Bullet Train’s Leitch was also the stunt double for Brad Pitt in six motion pictures – Fight Club, The Mexican, Spy Game, Troy, Ocean’s 11 and Mr. and Mrs. Smith.

Here’s my personal selection of Pitt’s ten best movies:

Once Upon a Time in Hollywood(2019) Amazon Rent/Buy

Pitt is superb in Tarantino’s love letter to late 1969s Hollywood playing aging stuntman (and suspected wife killer) Cliff Booth.

He is at ease in the role, boasting an impressive physique at 56, demonstrating a laconic way with QT’s dialogue, much better than his cornpone delivery in the director’s overrated Inglorious Basterds (2009).

Tarantino’s weird foot fetish intrudes (Dr Scholl should have been a sponsor) and some scenes play way too long, but the picture perks up every time Pitt is onscreen.

True Romance (1993), Amazon Rent/Buy

Pitt’s flair for comedy came to the fore in Tony Scott’s movie, written again by Tarantino. Knowing of Brad’s professed (former) enjoyment of weed, it wasn’t too much of a stretch for him to play affably addled stoner Floyd, but boy did he do it well.

Mr & Mrs Smith (2005), Netflix, Amazon Prime, Disney+

The movie that sundered the Pitt/Aniston marriage and saw the actor begin his eventually troubled relationship with Angelina Jolie.

It’s Spy vs Spy time in Doug Liman’s(The Bourne Identity) hit movie when mutually dissatisfied married couple John (Pitt) and Jane (Jolie) Smith don’t realise that each other are secret agents.

An action comedy of errors naturally follows when they do. The pair certainly had chemistry at the time, but it’s difficult not to watch through the lens of their later increasingly bitter personal and legal dustups.

Although a sequel reteaming the couple would certainly be interesting, it’s extremely unlikely, so viewers will have to settle for the upcoming Amazon Prime series with Donald Glover and Maya Erskine, who took over from Glover’s Solo co-star Phoebe Waller-Bridge who left due to that old excuse ‘creative differences.’

Seven (1997) Netflix, Amazon Rent/Buy

Some may find Pitt’s overwrought histrionics during Seven’s final ‘what’s in the box?’ scene a tad OTT, but he’s otherwise exceptionally good in David Fincher’s seminal noir thriller, an atmospheric trek through the Seven Deadly Sins essayed by Kevin Spacey’s creepy serial killer John Doe.

A shame them that the picture spawned a host of inferior imitators, including The Little Things, Solace, Kiss the Girls, Suspect Zero, Murder by Numbers, Untraceable, Jennifer 8, The Bone Collector and far too many others to mention.

Spy Game (2001)

The actor teams up with Tony Scott for this highly enjoyable espionage thriller where Pitt plays CIA operative Tom Bishop, mentored by superficially cynical Case Officer Nathan D. Muir (Robert Redford).

Redford had previously directed Pitt in A River Runs Through It (1992); the pair obviously got on as they have a natural onscreen relationship, which could easily pass for father and son. Redford was 65 at the time, Pitt 38.

The older actor gets the best lines. Redford displays some great underplayed humour as the foxy spy who effortlessly outwits his pen-pushing bosses.

Snatch (2000), Amazon Prime, Netflix, Amazon Rent/Buy

Pitt is easily the best thing in Guy Ritchie’s cringingly titled cockneys vs travellers vs gangsters movie, which has aged badly since its release back in 2000, suffering as it does from the director’s contrived public school take on the London crime world.

Pitt is on form as bare-knuckler boxer Mickey O’Neil, leader of an Irish traveller clan.

Speaking in a deliberately impenetrable brogue, the wily O’Neil is one step ahead of both erstwhile ally Turkish (Jason Statham) and nasty crime boss Brick Top (a genuinely menacing Alan Ford).

Snatch was pointlessly made into a two season TV series (2017-18) starring Rupert ‘Ron Weasley’ Grint. The best that can be said for the show was that it wasn’t as bad as Channel 4's 2000 series Lock Stock, a riff on the 1998 movie co-produced by Ritchie, then collaborator Matthew Vaughn and tiresome DJ Chris Evans. The series is notable in giving early roles to Martin Freeman (Sherlock) and Nikolaj Coster-Waldau (Jamie Lannister).

Ad Astra (2019, Amazon Rent/Buy

James Gray’s (The Lost City of Z), brooding sci-fi picture sees careworn astronaut Roy McBride (Pitt) on an Oedipal quest (minus the incest) to confront his father Clifford (Tommy Lee Jones), who in a Colonel Kurtz (Apocalypse Now) fashion has gone rogue on deep space facility Project Lima.

Gray wanted his film to have 'the most realistic depiction of space travel that's been put in a movie' which may or may not be the case, but he certainly gives it the old college try.

The pace is slow, and Pitt dials his performance way down (as required for the role), but there are also some extremely well-handled action sequences, including a lunar skirmish with rebel scavengers and a terrifying encounter with killer baboons on a space station.

For non-classical scholars Ad Astra is Latin for 'To the stars'.

World War Z (2013), Amazon Rent/Buy

Summer scarf sporting former United Nations investigator Gerry Lan (Pitt) takes on the Zombie Apocalypse in Marc Forster’s (The Kite Runner) enjoyably breakneck action horror.

Pitt holds the film together with an underplayed performance in a plot that throws the viewer a few curveballs, including the WTF self-inflicted death of a brilliant young virologist, and when overly loud religious chanting leads to the noise-sensitive zombies breaking into Jerusalem.

The picture’s climax occurs in a Cardiff WHO facility, which, as the saying goes ‘isn’t something you see every day.’

At least in Hollywood blockbusters, that is.

A couple of months before the release of World War Z sources claimed nervous distributor Paramount altered a scene in which the characters hypothesize that the zombie infection began in mainland China.

George Clooney paid tribute to his pal Pitt's behind the scenes efforts on turning the troubled, over-budget production around: 'I saw him in London when he was doing the World War Z reshoot…He just said, "This one’s going to kill me, man." It was a huge reshoot and Brad was putting it on his shoulders. He picked it up and put it on his shoulders and took it away from all the people who were screwing it up. Carried it over the finish line. Got it made into a film that was well reviewed and made a lot of money…'

The Assassination of Jesse James by the Coward Robert Ford, (2007)Amazon Rent/Buy

Chopper director Andrew Dominik helmed this revisionist Western depicting the events leading to the betrayal and murder of the folk hero bank robber (Pitt) by weaselly fame-seeker Robert Ford (Casey Affleck) and his brother Charley (Sam Rockwell).

Reviews were mostly favourable, with Mark Kermode going as far as to say that the picture was 'one of the most wrongly neglected masterpieces of its era.'

Nay-sayers objected to the length, lethargic tempo and what some saw as superfluous third-person narration (using the original temp track by assistant editor Hugh Ross) which literally described what was happening on screen.

Dominik (who also directed Pitt in 2012’s Killing Them Softly) joked that notoriously snail-paced auteur Terrence Malick (Badlands) said Jesse James was 'too slow.'

Pitt is the co-producer of Dominik’s upcoming Marilyn Monroe biopic Blonde, starringAna de Armas (Knives Out) as the disturbed screen siren.

The Mexican (2001), Amazon Rent/Buy

Director Gore Verbinski helmed this agreeably easy-going romantic crime comedy, where Pitt’s mob-indebted goofball Jerry Welbach travels to Mexico to collect a cursed antique pistol.

The Mexican echoes the shaggy dog road movies of the 1970s (Slither, Harry & Tonto, The Sugarland Express, Two-Lane Blacktop etc) where character is more important than the plot.

Welbach and girlfriend Samantha (Julia Roberts) encounter a gallery of rogues on their journey, including oddly sympathetic gay hitman Winston Baldry, played by the late James Gandolfini.

The Mexican made its nut at the box office, raking in $147.8 million on a $57m budget. Verbinski later found even greater financial success when he teamed up with Johnny Depp for the first three Pirates of the Caribbean pictures but came a cropper when they later reteamed for 2013’s bloated Lone Ranger, where Depp was Tonto to also later scandal-hit Armie Hammer as the Ranger of the movie’s title.