Worst To Best: Brad Pitt

Too Young To Die? (1990)

The Film: Another TV drama, this one’s based on a true story and paired Pitt with Juliette Lewis for the first time. She plays Amanda Sue, who kills a man and winds up on Death Row.

Rad Brad: Cringing away from the pretty boy image, Pitt brings real grit to his role as Billy Canton, and shows early promise as a dramatic actor.

The Image (1990)

The Film: Albert Finney plays Jason Cromwell, an investigative reporter whose dedication to his job means his personal life is taking a turn for the worse.

Rad Brad: Pitt plays Steve Black, a cameraman. Not exactly a glamorous role, but when you’re sharing the screen with Albert Finney, who’s complaining?

Happy Feet Two (2011)

The Film: George Miller’s sequel to Happy Feet . This time around, Mumble the penguin encounters a penguin with the ability to fly and must battle a blizzard that threatens to wipe out the Emperor clan.

Rad Brad: As Will the krill, Brad gets to play one of the better new characters the sequel has to offer – Will wants to move up the food chain by eating a larger animal. Cute.

The Devils Own (1997)

The Film: New York cop Tom O'Meara (Harrison Ford) gives shelter to a young man, unaware that he’s actually Frankie McGuire (Pitt), one of the IRA’s most dangerous assassins.

Rad Brad: A dodgy accent doesn’t detract from this being a fantastic performance as Pitt attempts to bury his nice-guy image as a ruthless killer. Pitt later disowned the film after a troubled production.

The Mexican (2001)

The Film: Criminal Jerry Welbach (Pitt) is under pressure from both his boss and his girlfriend. The former wants him to retrieve a ‘cursed’ gun from Mexico, while the latter (Julia Roberts) wants him to leave his life of crime behind.

Rad Brad: Pitt plays up the comedy as a criminal who’s clumsier than Mr Bean. The film’s hit and miss, but Pitt keeps things ticking over.

Two-Fisted Tales (1992)

The Film: A three-part anthology of horror tales co-written by Frank Darabont and directed by Richard Donner, Tom Holland and Robert Zemeckis.

Rad Brad:
Pitt appears in the segment entitled ‘King Of The Road’, which sadly doesn’t exactly make the most of his talents.

King Of The Hill (2003)

The TV Series: Mike Judge’s animated comedy series. Pitt guest starred in season eight episode ‘Patch Boomhauer’, an episode named after the character he plays – the brother of regular old Boomhauer.

Rad Brad: Pitt goes lothario in a vague reprise of his Thelma & Louise character. Nice.

Oceans Twelve (2004)

The Film: Least-loved in Steven Soderbergh’s Ocean’s trilogy, this second caper sees Danny Ocean (George Clooney) attempting three European heists. Meanwhile, Terry Benedict (Garcia) wants his money back.

Rad Brad: Jostling for space in a mammoth cast, Pitt stands out with a wry smile and a twinkle in his eye – and strikes up some sizzling chemistry with love interest Catherine Zeta-Jones.

Contact (1992)

The Film: Not the Jodie-Foster-alien-movie, but a war drama short in which an Arab and American soldier confront each other in the desert.

Rad Brad: The film was Oscar-nominated for a Best Live Action Short in 1992, which we like to think is thanks mostly to Pitt’s emotional turn as Cox.

21 Jump Street (1988)

The TV Series: The show that launched Johnny Depp’s career also featured an early appearance by Brad Pitt, who showed up in season two episode ‘Best Years Of Your Life’.

Rad Brad: As Peter, Pitt shares a brief canteen scene with Depp . He’s in firm jock territory, replete with football jacket.

Josh Winning has worn a lot of hats over the years. Contributing Editor at Total Film, writer for SFX, and senior film writer at the Radio Times. Josh has also penned a novel about mysteries and monsters, is the co-host of a movie podcast, and has a library of pretty phenomenal stories from visiting some of the biggest TV and film sets in the world. He would also like you to know that he "lives for cat videos..." Don't we all, Josh. Don't we all.