Classic Simpsons Reviews: “Oh Brother, Where Art Thou” lovingly torpedoes the American Dream™.

2.15 Oh Brother, Where Art Thou

Homer finds his long lost brother, an auto manufacturer named Herb. Herb gets Homer to design a car for him, but Homer ruins his brother by designing a monstrosity.

I think the chalkboard gag (“I will not sell land in Florida”) is a Glengarry Glen Ross reference, but I could be wrong. Regardless, it anticipates the episode’s theme of capitalistic hubris.

The Herb episodes are my favourite explorations of the so-called American Dream. The Simpsons is wonderful at presenting broad issues in a thought-provoking way without necessarily taking a hard stance that might ignore nuance. As they do with religion, the writers present capitalism as a relatively neutral mechanism that can yield positive or negative results depending on who wields it. For Herb, capitalism is the best and worst system there is. He rises to the top of the automotive world by doing dishes for rich people, and yet it only takes one bad decision to destroy everything he has worked for.


This pretty well encapsulates what The Simpsons has to say about the idea of the Everyman.

Herb’s energy and optimism bespeaks an undercurrent of “USA, USA, USA” (which he chants in his redemption episode in season 3), and yet he is bought out by a Japanese auto manufacturer at the end of the episode. That which provides him with opportunity proves fickle in the end, which is neither an endorsement nor a condemnation of capitalism; it’s a harsh analysis, but not an unfair one.

The Dr. Hibbert long lost brother mini-twist is delightfully Shakespearean. In writing The Comedy of Errors, Shakespeare decided “Hey, I’ve got one set of twins here, why not two! Just as Shakespeare pushes his comedy just a little further into the absurd to amplify the satire, so does The Simpsons.


An undeserving Homer gets his; a hard-working orphanage director does not. The covert criticism of the American Dream is so strong in this episode.

I think this episode and “Homer vs. Lisa and the 8th Commandment” might be the best early examples of the greatness we see in seasons 3 through 7. It’s equal parts sentimental and hilarious, with just the right amount of absurdity.

I love the rolling down of the limo window to reveal Herb as Homer’s reflection disappears. That’s some good storyboarding happening there.

Screen Shot 2015-11-27 at 10.45.30 AM

The bag of chips and the limo are a subtle and perfect juxtaposition.

As for Herb, Danny DeVito just absolutely nails him. He’s inspiring; an alpha, and yet so vulnerable. The hubris with which DeVito endows Herb is the antithesis of Homer’s, and yet comes from the same place. Homer is too selfish, obtuse, and lazy; Herb is too empathetic, too smart, and too enterprising for his own good. He wants to give an extraordinary position to an average schmo, because that’s how he, like Homer, started.

The brilliance of this episode lies in how you know what the ending is going to be; of course Homer is going to find a way to screw up and ruin his brother, but you don’t care because the journey is so good.

Like the dialogue:

Herb: “Homer you’re the richest man I know.”

Homer: “I feel the same about you.”

The writers were criticized for the sad ending, which sees a ruined Herb telling Homer he doesn’t have a brother as far as he’s concerned, but I’m gonna go to bat for the writers on this one. The episode ends with Bart telling Homer that he thought his car design was cool. That little scrap of validation is good enough for him, and so the writers frame it as a happy ending in spite of the devastation Homer has caused. A life was destroyed, but hey, at least Homer got a compliment. That’s a phenomenal commentary on the great big lie that the American Dream rewards exceptionalism; in truth, it rewards mediocrity far more often.

It’s not unlike the ending of Homer’s Enemy, where the supporting characters lovingly chuckle at a sleeping Homer during Frank Grimes’ funeral. The writers are critical of Homer here, and so are critical of the viewers for elevating him to hero status. I find that bold and insightful.

Best Moment: The reveal of “The Homer,” Homer’s awful car design.


The Simpsons doesn’t imitate real life; real life imitates The Simpsons.

Best Quote: “You know that little ball you put on the aerial so you can find your car in the parking lot? That should be on every car!” -Homer

Yes, it’s a real thing.


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