George Clooney’s Jail Break Is The Ultimate Fugitive Comedy

By Robert Scucci
| Published 1 hour ago

One of my favorite live albums of all time is Thin Lizzy’s Live and Dangerous, which opens with the certified banger, “Jailbreak.” Something about kicking off a 76-minute, double-LP masterpiece with a high-energy tune about running from the law sets the tone for some serious rockin’ and rollin’. The same could be said about 2000’s O Brother, Where Art Thou?, the ultimate jailbreak comedy by the Coen brothers.

Starring George Clooney, John Turturro, Tim Blake Nelson, and John Goodman as a menacing cyclops, this flick is fun personified as our heroes and many antagonists become legends through their own fabricated folklore, one iconic song about endless sorrow at a time.

We’re In A Tight Spot!

Based loosely on Homer’s epic The Odyssey, O Brother, Where Art Thou? wastes no time introducing us to Ulysses Everett McGill (George Clooney), Pete (John Turturro), and Delmar (Tim Blake Nelson), three convicts who escape their chain gang in search of treasure and other payoffs that eventually reveal themselves. Right off the rip, they find themselves in a tight spot. The authorities are hot on their tail, their resources are limited, and Ulysses is about to run out of hair product.

Along the way, they encounter and assist notorious bank robber George “Baby Face” Nelson (Michael Badalucco), and meet a blues musician named Tommy Johnson (Chris Thomas King), who claims he sold his soul to the devil for mastery of the guitar. They unwittingly write and record a major hit song while on the run, fall victim to singing sirens washing themselves in a lake, get assaulted and mugged by a crooked, one-eyed bible salesman named Big Dan (John Goodman), and that’s not even half the chaos they wander into.

Each Setback Leads To Another Unexpected Victory

As their adventure becomes more ridiculous in O Brother, Where Art Thou?, the pieces slowly fall into place, and the consequences of their choices pay off in unexpected ways. In typical Coen brother fashion, we get a live-action movie that behaves more like a cartoon.

Think of it as a 1930s period piece with the same wild energy as Raising Arizona or The Big Lebowski. There’s an inherent absurdity that sells the premise without forcing you to take any of the beats too seriously.

The magic of O Brother, Where Art Thou? is that it tackles heavy topics like the flaws in the American penal system, race relations, corrupt politicians, and how sometimes you have to make the best out of a sticky situation by pressing forward with sheer grit and determination. These guys aren’t necessarily terrible people, but they’re absolutely a product of their environment, trying to find greener pastures while laying low from the law. Their shared goal is simple: secure a fortune that lets them finally live peacefully and prosperously.

A Stylish Satire That Isn’t Afraid To Lean Absurd

By channeling beats from Homer’s Odyssey, O Brother, Where Art Thou? works more as mythology than realism, which helps the story by letting viewers suspend a healthy amount of disbelief. Every incident, no matter how small or profound, eventually leads to a payoff that ties everything together in ways that would never happen in real life.

With its supernatural level of good luck and well-timed coincidences, the film takes you on a wild ride through a Depression-era United States that becomes believable within the rules of its own fiction. Everybody feels vaguely aware that they’re part of an epic tale without ever admitting it out loud, which only adds to the charm.

A quick-witted story about trusting your instincts, following momentum, and relying on your friends when the road gets rough, O Brother, Where Art Thou? is as surreal as it is playful. It’s the kind of revisionist history for the sake of comedy you see in films like Forrest Gump in the sense that it takes place in the real world, but everything’s heightened and exaggerated for storytelling purposes.

The result is a cheeky adventure that never wears out its welcome because you want to see these guys reach the end of the road. The final payoff is worth every unexpected turn they take.

O Brother, Where Art Thou? is streaming on Hulu.