Last time we had an episode centered around Marge’s well-known (and well-despised) twin sisters, so I think it’s fair we give Homer’s family a chance in the spotlight this time. However, let’s introduce a character that we (and Homer for that matter) never knew existed in the first place. It’s time we go deep into the lore of The Simpsons as we get introduced to Herbert Powell, Homer’s lost, half-brother, voiced by the one and only, Danny Devito.

“Oh Brother, Where Art Thou” is the fifteenth episode of The Simpsons second season, but much like Principal Charming, was written after the following episode, just pushed up in the broadcast order, and it debuted on February 21st, 1991. The chalkboard gag for this episode is, “I will not sell land in Florida,” and the couch gag features the family sitting on the couch with Maggie peaking her head out of Marge’s hair at the end (the same gag used in Dancin’ Homer).

Director: “Mr. Simpson, your brother could be anywhere. Even…Detroit.”
Homer: “I know he could be anywhere. That’s why I want you to narrow it down! Please!”
Director: “You know Mr. Simpson, if you ask me, the city of ‘brotherly love’ isn’t Philadelphia, it’s Detroit.”
Homer: “Well if you ask me, changing the subject makes you the most worthless, heartless excuse for a human being I ever…”
Director: “Read between the lines you fool!”
Homer: “Oh I get it! Okay! Here’s twenty bucks. Now can you tell me where he lives?”
Director: “Mr. Simpson, I…”
Homer: “Just take it and tell me!”
Director: “Detroit. He lives in Detroit.”
Homer: “Fine! THANK YOU!”

After seeing the McBain movie at the movie theater, Grandpa has a mild heart attack and is taken to the Springfield Memorial Hospital. When Homer goes to visit him, Grandpa, fearing that he doesn’t have much longer to live, decides to tell Homer a family secret. When Homer’s mother and he were dating, Grandpa had a romantic run-in with a female carnival worker, which produced a baby boy. With the mother unable to take care of the baby, and Grandpa not ready for children, he put the baby up for adoption at the Shelbyville orphanage. A year later, Grandpa got married to Homer’s mother, who gave birth to Homer around the same time. After the revelation, Homer decides he wants to meet his lost, half-brother and starts trying to track him down.

From the orphanage, Homer discovers that his half-brother is named Herbert Powell and that he lives in Detroit. He finds Herb’s phone number and gets to talk to his brother for the first time. Both overwhelmed with emotion, Herb invites Homer and his family to come visit him. While the family is on the road, we find out that Herb is the owner of a car company named “Powell Motors,” a company that has not only made Herb a millionaire, but is currently not performing well in the marketplace, and Herb fears it’s because the company is losing touch with the “average Joe” consumer. Herb is also feeling distraught because he is very uncertain of his own roots and is a very lonely guy.

The Simpsons arrive in Detroit and Homer finally gets to meet face-to-face with his long-lost, half-brother. Herb looks nearly identical to Homer, aside from the fact that Herb is skinnier and has way more hair. The meeting is very emotional as both grown men end up in tears. Homer introduces Herb to the rest of his family and Herb makes it very clear to them that he is very rich, lives in a mansion, and is not shy about spoiling them.

Herb takes Homer to his car company and decides to give him a car, but when they don’t have any cars that Homer wants, Herb gets angry at his employees, proving his point that the company isn’t doing well because they aren’t catering to the demands of the common man. This gives Herb an idea, as he asks Homer if he will help him design a car for “all the Homer Simpsons out there.” Homer is at first hesitant but agrees when Herb tells him that Homer will be paid as well if the car is successful.

Homer is at first unable to put any influence on the car’s design, but after a pep-talk from Herb, gets a lot more confidence in himself and starts designing a car that he thinks will be cool. Herb’s staff is extremely worried and concerned about the project, but Herb remains confident in his brother and continues to enjoy himself in the thrill of having a family and spending time with Homer’s kids.

The car is finally ready, and Herb decides to hold a special presentation for the car in its first unveiling, still not having seen it himself. When the car is finally revealed, Herb is shocked by the incredibly over-the-top design, and the unnecessary inclusions of several, impractical features. When one of his employees reveals the sticker-price of $82,000, Herb comes to the realization that his company is finished, as nobody wants to buy the car and it was way too expensive to produce as it is.

Powell Motors is shut down, Herb loses his mansion, alongside all his possessions, and now must say good-bye to the Simpson family. When Homer tries to say goodbye and apologize for ruining his career, Herb gets angry at Homer, saying that his life would have been better off if he had never met Homer, and that as far as he is concerned, he has no brother. Homer is hurt by Herb’s words, but while the family is driving home, Bart makes Homer feel better by saying that he at least thought Homer’s car looked “really cool.”

Marge: “Bart! Lisa! If you two don’t behave, we’ll turn this car right around and go home!”
Homer: “But Marge! I want to see my brother.”
Marge: “Oh for God’s sake Homer, it was an empty threat.”

Personal History:
This was another episode on my VHS tape, and an episode I remember really liking as a kid, just because I thought the premise of Homer having a brother, one we never knew about, was interesting. I never really understood the plot, or why Herb hated Homer so much at the end of the episode (because like Bart, I was a kid and also thought Homer’s car was really cool), but it was still a fun episode to watch as a kid. I guess in a way, I kind of related the episode to my life to a large degree, because both of my uncles had always lived far away from me (one in Pennsylvania, and one in Arizona, while I lived in Indiana), and always loved it when they came to visit us, because they were relatives I never got to see often and it was always exciting to have them around. I guess I saw a lot of me in the Simpson children, and a lot of my uncles in Herb’s character, because my uncles seemed like they were very dedicated to try and make me happy, and to get me to see them as the “fun uncle” type of role, something Herb was not shy about doing in this episode. These days, I’d say the Homer & Herb storyline is the more important aspect of the story, for sure, but as a kid, you obviously don’t think about it to that degree.

Herb: “You’re gonna hang up, call me back and say the exact opposite of everything you just said to me. Got it?”
*ends phone call*
Herb: “Bart! Lisa! I want you to hear what the guys at the plant think about your old man”
*phone rings, Herb answers and puts it on speaker*
Worker: “Homer Simpson is a brilliant man with well thought-out and practical ideas. He’s ensuring the financial stability of this company for years to come. Ah yes, and his personal hygiene is above reproach.” 

Favorite/Memorable Moments:
The first thing I will address is perhaps the biggest elephant in the room, and that is the character of Herb Powell being played by Danny Devito. Devito absolutely owned this role and because of that, this is probably one of my favorite guest roles of all time in the Simpsons universe for how excellent the delivery and the character is. It’s honestly a shame that they didn’t get to use this character more, but as I’ll talk about in his appearance in a future episode, it’s probably better that this character arc lasted only two episodes anyway, just in the interest of not wearing out the character and making the appearance more special and significant in the process. As far as the character itself is concerned, I think he was written quite well. Herb is a straight-up businessman, not afraid to speak his mind or agenda, and who has worked his ass off to be successful, even if it was at the cost of a lot of life’s other joys. Because of his “unique” family situation, I imagine the thought of him being adopted must had weighed heavily on him, which caused him to feel quite lonely as he was growing up and aging; always wondering why his actual parents never kept him. Then, when Homer and his family show up, he starts to feel like he has a second chance. He has a family that’s related by blood, something he has never known before; therefore, he starts to let his guard down and have more fun with the rest of the family. Unfortunately, this development is ultimately what kills his professional career because he decides to turn a blind eye to Homer’s car project, because he thought he could trust Homer. However, I can see this as him losing himself in the moment when he was at his happiest. In a way, this plot kind of makes him a bit of a tragic character, someone who either unhappy, but successful, or happy, but a failure, and I think that’s brilliantly depicted in this episode. It’s an easy, cliché premise, but it gets the job done, and boy is it done well.

This episode just has a ton of funny moments and quotable lines for me. Every character here has at least one very good moment in the spotlight, from the very beginning to the very end. At the beginning of the episode, I love when Grandpa is retelling the story of how Herb came to be and it ultimately ends with Homer’s mother telling Abe to never tell the story of the carnival lady to Homer, and then Grandpa, in present day, realizing that he had just broken that promise, tries to backpedal and get Homer to forget everything he had just revealed to him, after it had already sunk in to Homer. Then when Homer is talking to the person who works at the orphanage in order to find out where Herb lives, the exchange he has with the guy is perhaps the best moment of the episode for me. The guy at the orphanage is heavily hinting at Homer that Herb lives in Detroit, but Homer doesn’t get it and proceeds to beg and yell until he can get an actual confirmation. It gets to a point where the man even shouts “read between the lines, you fool!” just for Homer to pay a bribe and get the actual confirmation.

The second act is perhaps the slowest act in terms of plot progression, but it’s a very important part of the episode just because it’s when Homer and his family finally get to meet Herb, so it’s a very special part of the story. We get to see the Simpson family stare in amazement at Herb’s success, and Herb is finally introduced and reunited with his actual family. It’s a good moment of the episode and is probably one of the top emotional moments from season two. My only critique or complaint of this act are the small scenes leading up to when Herb is revealed. I think we could have done without the scenes of the family driving to Detroit, just because they don’t really add much to the story as a whole, and I think the time could have been used better for furthering the plot of the third act or even giving Herb some more time interacting with the family; maybe a quick scene for each of the kids with Herb, just to emphasize how important having a family is to him.

The final act is basically dedicated to Herb, at the peak of happiness, being brought to his ultimate downfall and destruction. It’s a shame what ultimately happens to the guy, and I do feel for him, but I think the writers and showrunners ultimately made the correct decision in setting up his downfall. As I stated before, Herb turns a blind-eye to what Homer is doing when it comes to the car development, just because he is so happy with his newfound family, and as a result, that blind-eye is ultimately what gets him. Even if he were to just check in on the progress, he would have seen that Homer probably isn’t the type of guy who should be calling those kinds of shots and could have probably had a nice laugh about it and still had his new-found family by the end of the episode. Instead, he’s certain that his plan would work, and that small bit of overconfidence and egotism is what kills his career. I really like the quote Lisa says at the end of the episode when she says, “his life was an unbridled success until he found out he was a Simpson,” because what happened to Herb is something you would expect to happen to a Simpson family member, and even though it pushes Herb away, in a strange way it also kind of makes Herb part of the family as well. The Simpson family doesn’t ever succeed, they just kind of go through live and its many adventures and live with whatever comes to them.

The last thing I want to talk about in this section is the car that Homer develops in this episode. The car is an absolute travesty, a ridiculous concept for a vehicle, and is perhaps the worst idea for a car I’ve ever seen…and yet, I absolutely love it at the same time. This car is very iconic to me, because it really reminds me of what little kids in school would draw when given the task of drawing their dream car; something that looks incredibly over-the-top, almost futuristic, and designs that are completely and utterly impractical. I think it perfectly represents the mindset of Homer as well; just because Homer is a grown man in his mid-thirties, yet he has the mind of a child, so I can completely see this design coming from him in a very serious manner. Also, as a fan of “The Simpsons: Road Rage” and “The Simpsons: Hit & Run” videogames; I really appreciate this car making a special appearance in both of them, especially when you consider it’s supposed to be one of the best vehicles in both of those games.

“All my life, I have searched for a car that feels a certain way. Powerful like a gorilla, yet soft and yielding like a Nerf ball. Now, at last, I have found it!”
~Homer Simpson (ad for “The Homer”)

My Review:
“Oh Brother, Where Art Thou” is not a perfect episode by any means, but it’s an episode I really enjoy and is perhaps one of my highlights of Season 2. They introduced a great character with an amazing voice talent backing him up, there are a ton of very memorable and hilarious quotes and scenes, and even delivers on some good emotional scenes as well. As I said before, my only negative critiques of this episode come from the fact that I think some scenes could have been omitted for the sake of giving us more build-up and development of the plot that kind of gets rushed through the third act. It’s not that the scenes we got were bad, per say, it’s just that those scenes could have been repurposed a bit to have more relevance with the actual plot going on and giving more meaning to what ultimately happens with Herb here.

Even with that though, I think this is a fantastic episode and is one of my favorites from Season 2. It was one of my favorites back in the day, and I think I can safely say it’s one of my favorites of this season still. I look forward to looking at the sequel to this episode, “Brother, Can You Spare Two Dimes?” a Season 3 episode that continues the plot of Herbert Powell, but since that is the finale of that season and we still have the rest of Season 2 to get through, I wouldn’t expect that retrospective for a while. However, it’s something to look forward to, for sure. And with that, I think that’s all I have to say about this episode.


Ok, that will do it for another Season 2 episode. Apologies again for this one taking so long to publish, as I definitely had most of this ready for a couple of months now, but as I’ve said before, real life comes first and my Youtube and Twitch channels come second, and there’s a lot of things progressing on all of those fronts, so once again I had to put this on the back-burner. I am glad I got this up though and curious to see what episodes await us, as we approach the final seven episodes of the season. Speaking of which, the next episode is… “Bart’s Dog Gets an ‘F.’” Well now, I can say for certain that review will have a much different tone than this one. See you guys then!

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