Herb Powell has only appeared on two episodes of The Simpsons—in a later episode he’s referred to as Homer “seldom-seen half brother”—yet he’s depicted with more complexity, depth and pathos than the lead characters in most television comedies.
Herb is a staggeringly complicated figure, the big-hearted and rage-filled product of a sordid fling between Abe and a carnival prostitute (are there two more intoxicating words in the English language?). He's also sort of a modern-day Tucker, a maverick beating Detroit at his own game. He is both an Ivy League over-achiever and a man innately in touch with his working-class resentments. To borrow the only line from A Beautiful Mind that I remember, he’s balanced in that he has a chip on each shoulder.
Herb is both a righteous working-class shit-kicker and a Charles Foster Kane-like mogul who gained everything in the world but what he wants and needs most: a family. He can be tremendously tender and kind or a screaming, bullying bastard. It’s almost a shame the show hasn’t done more with him, but there’s something to be said for quitting while you’re ahead.
“Oh Brother, Where Art Thou” plays almost like a Preston Sturges/Frank Capra screwball morality tale about the innate decency and wisdom of the common man turned on its head. If the episode were, in fact, a Frank Capra movie, the lonely and frustrated autocrat would be redeemed through his relationship with his exceedingly common half-sibling.
In The Simpsons’ warped world, the lonely and frustrated autocrat is destroyed by his relationship with his exceedingly common half-sibling. The episode twists the knife a little further by having Herb leave Homer in a furious rage, not a Zen-like state of forgiveness and acceptance. Homer may have ruined his brother’s business empire with his bull in a china shop like ways, but at least his brother will never stop hating him.
“O Brother Where Art Thou” opens with an inspired parody of Arnold Schwarzenegger bloodbaths starring the show’s Schwarzenegger surrogate Rainier Wolfcastle. The film enrages Abe to the point that he has a heart attack. In the hospital afterwards, Abe tells Homer a closely guarded family secret: He has a half-brother by a carnival prostitute who would do things that Homer’s mother wouldn’t, like have sex for money.
In a fit of rabid curiosity, Homer tries to get the head of the local orphanage to reveal the location of his long-lost sibling, only to be flummoxed and confused by the Dr. Hibbert lookalike’s not-so-subtle hints that his brother lives in Detroit. The administrator finally just gives up and tells Homer, who is delighted to discover that the brother he never knew now occupies the very tippy-top of the socioeconomic ladder.
Homer and Herb’s reunion begins like a fairy tale and ends like a nightmare or at the very least a bad dream. Herb is overjoyed to learn of Homer’s existence and treats him and his family to the finest things in life, like getting to interact with zoo animals during a private tour (nothing is off limits to those with enough money) and, in Homer’s case, getting to custom-design the ultimate car.
If this were Mr. Deeds, the Homer-engineered car would be a thing of beauty and a cash cow. The car’s superior engineering and popularity would prove the simple wisdom and superiority of common folk over the snobbery of the moneyed elite. But this isn’t Mr. Deeds and Homer creates the ultimate monstrosity; imagine The Edsel and the Pinto hate-fucking a moon buggy and you have something close to The Homer. It's Homer's id in vehicular form, the least practical and most expensive means of transportation this side of a stretch Hummer.
“O Brother Where Art Thou” isn’t just a spectacularly funny episode with considerable pathos, heart, and black humor; it’s also a scathing satire of the Cult of the Common Man and the boorishness of the Typical American Consumer. It operates on multiple levels, beautifully.