The most challenging performance of George Clooney's career

The one role that made George Clooney anxious was probably one of his most fruitful, as it led to a long-standing collaboration and allowed him to break out of his mould.
The most challenging performance of George Clooney's career

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(Credit: Universal Pictures)

Film » Cutting Room Floor

Sat 1 February 2025 21:15, UK

George Clooney is Hollywood’s consummate leading man, known for his dashing good looks and natural charisma. Clooney has had quite a career: the face of the stylish Ocean’s Trilogy, twice the winner of Academy Awards and the star of Batman and Robin – which was successfully branded as one of the worst films ever made.

Not satisfied with just succeeding as an actor, director and producer, Clooney also co-founded a tequila brand that sold for a near billion dollar fee and does extensive philanthropic work through his Clooney Foundation. Leave something for the rest of us, George. Having achieved such artistic and entrepreneurial success, along with surviving an attempt at career suicide, you’d think that nothing could melt Clooney’s effortless cool.

That was until accepting a role in the Coen Brother’s 2002 cult classic, O’Brother, Where Art Thou. The film began production in 2000, with Joel Coen travelling to Phoenix to offer the role to Clooney, who accepted without even reading the script while he was working on Three Lions. However, he has since said that ‘’[O’ Brother, Where Art Thou?] was definitely the scariest [role] for me, because I knew I would have to play a character.’’

The film, a loose retelling of Homer’s ‘Odyssey’ set in rural Mississippi in the 1930s, casts Clooney as a smooth-talking conman with a penchant for hair jelly. While everything doesn’t play out as smoothly as an Ocean’s heist for Ulysses, the role earned Clooney significant acclaim and helped to mend some of the damage caused by his ill-fated portrayal of The Caped Crusader a few years prior. Clooney himself referred to the role as his big break in Hollywood, describing the Coens as mentors. 

The story goes that he even reached out to his Uncle Jack in Kentucky as he prepped his accent for the character, specifically asking him to read the script into a tape recorder. Unbeknownst to George, his Uncle, being a devout Baptist, skipped every instance of the words ‘damn’ and hell’ through the entire script. Clooney told Vanity Fair that he had thrown the script out and worked directly from the tape, meaning he only discovered his Uncle’s unintentional re-writing of the Coens screenplay when they pointed it out to him on set.

This wouldn’t be Clooney’s only collaboration with the Coens, but rather the beginning of a long-running creative partnership. He went on to appear in three more Coen Brothers’ films, including Burn After Reading and Hail Caeser. Along with O’ Brother, Where Art Thou? these particular films form what Clooney referred to as his ‘trilogy of cowardly idiots’. His characters in O’ Brother, Where Art Thou and Hail, Caesar! are notorious for their ineptitude, though it could be argued that Brad Pitt picked up most of the idiot duties come Burn After Reading.

While Clooney was initially anxious about this role, it’s clear that the risk paid off in spades. It sent the message that Clooney wasn’t hitching his horse solely to the Cool Dude wagon, and could survive a joke at his own expense. This is more than can be said for quite a few of Hollywood’s contemporary leading men.

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