At first, I didn't want to start a feud with Herb Powell by doing this video. But then I realized he is a fictional cartoon character that can't do anything about it. This is another reason why Herb Powell sucks.

"There isn't enough material for a Simpsons Histories on Herb" - man who made a Simpsons histories on Just Stamp The Ticket Man

I wouldn't be surprised if Herb made that voicemail to make sure nobody asks him for cash and he's got money.

What'll always get me about Oh Brother, Where Art Thou? is that Herb hated the idea of naming a car Persephone, but was completely fine with calling a car Homer. It tweaks my sense of humor every time.

For Herb to have become destitute so quickly probably meant he was spending well outside his means. So I can believe he was poor in Changing of the Guardian, he probably overspent his fortune and whatever he was making off the baby monitor business couldn't keep up. Though he probably was better off the second go-around if he could afford a phone plan that included an answering machine. He's probably "living in a rundown bachelor pad" poor, rather than "living in the streets" poor.

Homer did nothing wrong. He tried to tell Herb he is not the person who should design his new car, twice, and he was ignored each and every time. It's literally Herb's fault and no one else's. Also the fact he never checked on the project AT ALL until the public showcase.

“Danny Devito is awesome, but Herb Powell sucks” Truer words have never been spoken

What I find the most unbelievable about Herb is how he, the CEO of a huge car company, somehow became homeless from his company failing. How many bad financial decisions did he make?

Now that I think about it, Herb blaming Homer actually feels more like a coping mechanism than anything. Imagine that you sunk your own company and it's entirely your fault, can you imagine how that would feel? I imagine that this would completely eat up Herb inside, that he'd look for any rationalization for what happened. Maybe Herb has a habit for projecting, since in season 24 we hear that he's bankrupt again, maybe he's actually gotten bankrupt many times before and just kept blaming other people for his downfalls. Like that could be why he seemingly doesn't have any contact with his parents anymore

All of herb’s failures in business can be summed up with this one Simpsons joke, “you got greedy, Martin!”

We NEED "Agnes Skinner Sucks", she's arguably the most hateable member of the reccurring cast for many reasons. Not only is she an abusive mother and a backstabber, she won't even let a little girl sit next to her in the bus.

That's an interesting observation I never noticed about Herb's out-of-touch nature. Considering his "clawed his way to the top from the bottom" origins, you''d think he'd be in touch with the "average" American and wouldn't need to rely on Homer.

Maybe he does but Mr. Devito just makes him so damn likeable

"I knew I kept the wrong one." - Abraham Simpson upon learning of Herb's wealth Herb is his father's son. That's not an excuse to behave as he does, but it's an explanation. The world taught him that relationships are always transactional.

The first time I saw Herb say to Maggie "you're going to make me rich" I remember thinking the episode was going to be him kidnapping her or holding her for ransom. They really did try to play with Herb's intentions when he came back.

One thing that always bugged me from these two episodes is that they feel rather like they belong on a cute 80s sitcom rather than The Simpsons. I have nothing against cute family moments on the show but these two episodes fell nothing like they're nothing BUT that. Another thing that bugged me was the complete lack of Grandpa in the second episode. For all intents and purposes he IS Herb's biological dad and he wanted to meet him in the first episode, which he doesn't but is justified by him arriving late after coming out of the hospital (which admittedly gives us the funniest bit in the episode: "I knew you'd blew it!"). But they don't even bother with an excuse in the second episode, it's not even brought up. It would have made for some interesting interactions to have those two finally meet, but instead we have to cope with more scenes of Herb being a jerk to Homer. Great video, btw.

His employees told him Homer's ideas were awful, and Herb just doesn't listen. Lisa was right, his biggest flaw in business is that he's a Simpson.

My least favorite thing about Herb is that he hires Harvard cronies that he hates when he could fill those positions with more average or self made people. Herb had to work his way through school, and instead of lifting up other people who are driven and industrious, he surrounds himself with rich snobs. He resents them so much that it leads to the Homer debacle and his downfall, so why did he hire them?

It always stood out to me that Herb wasn't one of the family members Homer called in the Simpsons gene episode. He would have been an example of a (somewhat) successful male Simpson. Also Apu should've gotten one of those baby translators.

I'm all for this becoming a recurring series, taking looks at characters like Herb that either show up too infrequently to be a regular or something you had thoughts about already, and then making this kind of mixture between Simpson Histories and Showdowns wherein you look at the positive and negative aspects from their spotlight episodes. Would be great to see and listen to.

I feel like it was a really missed opportunity that they never made more Herb episodes of him slowly growing closer to the family. Ending with him apologizing for his missteps on the way to meeting his brother.

I appreciate this take after decades of back and forth. I dont think anyone who likes Herb is bad or smth stupid but this delightfully captures how i personally feel about the issue

This is the kind of fair and balanced journalism the world so desperately needs today.

Concerning the baby translator, it's weird it got ignored in concept, though it's also kinda logical it would be ignored in The Simpsons universe. I could 100% see almost every deadbeat parent in the series trashing the thing after their baby gives too many specific requests or says too many awkward revealing things in public. Like with old people, this is an asshole universe that wants as many people inactive and as manageable as possible. Hell maybe this is what caused Herb's second downfall.

Hank Scorpio, who was an evil supervillain, acted more like a loving brother towards Homer.

Your point at 10:15 is something I noticed about this episode from the first time I watched it. People hated Ford’s Edsel, but the company didn’t disappear because of it. Herb’s company was clearly quite successful at one point. But, if a single bad product launch completely and totally destroyed it, Powell Motors was already on the very brink of disaster anyway.

How about "Jacqueline Bouvier Sucks" next? In "Moaning Lisa", her advice to Marge, just woof! In "Bart vs. Thanksgiving ", she comes into the Simpson household from the back side, and just so happens to walk by the kitchen window to spy on Marge's kitchen activities to look for something to nitpick, and then her very first words to Marge in the episode are "I have laryngitis, and it hurts to talk, so I'll just say one thing: You never do anything right." In "Lady Bouvier's Lover", she dumps Grampa for Mr. Burns at the drop of a hat, and scoffs at Marge's objection to marrying Mr. Burns, "That man is scum!", to which Jacqueline replies, "Then, call me Mrs. Scum..." Finally, she outright refuses Grampa's ask to marry him instead of Mr. Burns, albeit also dumping Mr. Burns at the altar, which is as close to her not sucking as we will ever get with her. Oh, and how she treats Homer in both flashback episodes "The Way We Was" and "I Married Marge", ugh. Clearly, Patty and Selma take after her...

*Reads Title* "Say what?"

Being voiced by Danny DeVito is the only redeeming thing about Herb.

Herb sounds like a broken man with a history of trauma. Perhaps his upbringing was very difficult, thus he was constantly on survival mode. Without any warm and connections, he only saw money and wealth as a indicator of one's worth in the world, hence he strived to make to the top of the corporate world. He was at a mid-life crisis when the Simpsons arrived, and he immediately bonded with Marge, Maggie, Liza and Bart as they were the family and childhood he never had. That's one of the reason he shirks his responsibility at his company, he even told Bart how he just wanted to watch cartoons all day, etc. His anger towards Homer was misdirected as it appears he never showed his vulnerabilities, but he opened up to the Simpsons. The results, he let his emotions override his logical mind and it brought him ruins. I wish they brought him back on the show or at least referenced him. Not him being poor, but maybe how he's still rich and reconnected with his humanity. That he's out saving people, like Moe.

Herb is the downside of having a famous person voice a character. He deserved to be in more episodes considering he's Homers half BROTHER.

Though I agree with some of this, I don't think Herb is completely bad. The bond he forms with Bart and Lisa is completely genuine. Him asking them to teach him about cartoons as well as asking them to call him Uncy Herb is endearing and taking them for pony/boat rides is something he didn't have to do (it may have spoiling them but that's not uncommon for aunties/uncles with no kids of their own). He's also pleased to see Bart and Lisa despite not having anything to gain from them unlike he does from Maggie. So yes, I do agree that Herb is a bit of a dick but I think there are good characteristics (mainly his fondness for his niece and nephew) that are glossed over here. It's also relative since Abe only seemed to want to know Herb when he knew he was a millionaire and after he found out Homer wrecked it, never mentions him again.

Honestly i think its all a victim of the show's style and Herb being a guest star. They needed clean cuts at the end. Easiest way to do that is to have something that makes Herb go far away from the Simpsons. If he was voiced by a regular, heck have Dan Casteleneta voice him then Id expect him to play a bigger role. Honestly I often wish the simpsons would do that a little more. Not that we need an infinitely growing cast but just keeping and paying off these characters we meet more.

If Herb were to have another episode centered around him, what would you want it to be like?

Something that comes to mind as an interesting angle given the "maybe he found another half sibling" is the idea that a show could be around herb constantly meeting new siblings,getting rich,and then falling apart due to either himself or others. Would certainly be a good reason to have a answering machine to say hes poor

I still think a episode about a famous location, like Moe's tavern, Springfield elementary, or the town hall would make a good episode. The one about evergreen terrace was great!

I like how Jims created a series purely from hatred of a fictional character. The pettiness is palpable and I love it.

I remember watching the episode where Herb gets introduced and i genuinely still think the reason Herb basically swaps his life with Homer's (Putting Homer in charge of his company being the main example of this) wasn't so much that he wanted to experience what it's like to have a family, but i think he was absolutely trying to take Homer's place in the family.Oh Brother, Where art thou is such a weird episode with a genuinely baffling ending. I also felt so bad for the executives and car designers this episode, they're painted as being bad, despite them actively being in the right and actually wanting to steer the company away from the obvious failure that Homer's design is going to cause, but Herb completely shuts this down.

I was SOOOO hoping you would actually make this video, my admiration is immeasurable and my day is made

"I don't know what happened in Herb's personal life", the guy was literally abandoned at an orphanage as a child

I feel bad for Homer. He did the damndest to make his half-brother proud, but all of that led to him being disowned. And even after that Homer still held next to no grudges toward him. Poor guy.

This video is like Succession to me lmao. But seriously, being able to actually see an in depth look at how and why Herb Powell is a terrible person despite how the narrative frames him actually makes me more empathetic towards him while also completely agreeing with your points. The idea of Herb being so scarred by his business failings as the Simpsons came into his life that he now views all family relationships as a means to a financial end is so tragic, it makes me feel bad for him while also still seeing him as completely in the wrong. I love how this video was able to add some depth to a controversial guest star character while still 100% agreeing he sucks.

Herb is a schmuck and I love him for it. The Herb Powell episodes were just so unique. There is no other Simpson episode like “oh borther, where art thou”. Its such a unique hang out episode so early into the show. If the whole episode was just them hanging out, I would probably like it even more. In “Brother, can you spare a dime”, seeing the level of hostility he has towards Homer is definitely off putting. Like it feels like the writers of the episode only watched the end of the other episode. Regardless, it is fun watching his journey to the Simpson family and seeing him spend time with Maggie. In conclusion Herb Powell sucks but his episodes are so unique and different I wouldn’t want him to be any other way.

Despite him sucking as a character, I think he could work as a semi-reoccuring character who shows up for an episode every other season. Much like Sideshow Bob. They managed to get at least 10 Bob wants to kill Bart episodes out of that. They could easily think of some for Herb to antagonise Homer or they work together for a get rich quick scheme which blows up in their faces.

7:15 or Herb has Homer's number screened to play that message to keep homer from ever asking for money back.

This title made me laugh out loud when I saw it pop up 😄 Perfect follow-up good sir.

Homer tried his best with his brother both times but Herb obviously doesnt appreciate him.

NGL if an US-based manufacturer made a compact named Persephone in the 90s I'd be obsessed with it today

I absolutely love these two episodes, especially the second one, but that’s because I’m not overly fussed about whether Herb is “good” or “bad” person. I’be never been too invested in his emotional arc, if indeed he has one. When it comes down to it, they’re just really really funny episodes, and Danny DeVito’s performance absolutely crackles with energy and charisma. That’s what these episodes are really about for me.

This was the first video of yours i ever watched, and it got me instantly hooked

I never liked the theme of "The Simpson family is doomed to failure and ruin everything they touch" theme in some episodes, and this is a perfect example as to why. This wasn't a case of Homer receiving power and getting in way over his head, he literally shared his insecurities with Herb, and got pressured into moving forward anyway. The show has a tendency to get really men spirited sometimes, which can work, but it feels cruel when all Homer really wanted was to have a relationship with his half brother.

The fact that he was only in two episodes tells us that the writer's thought Herb sucked to. After all, it can't be that Danny Devito is expensive, because they replaced every other celebrate voiced character with a regular. (Like Krusty's daughter.) Hell, the fact that the staff felt they needed an episode to fix his first appearance says it all.

I am praying, begging even, that in the future iterations of this not-yet series the counterargument section remains "The obligatory "Maybe Herb doesn't suck that much" argument". Not "Maybe Barney doesn't suck" or "Maybe Willie doesn't suck that much", just keep it "Herb" regardless of the character Also... like... I don't know where to say this but I always thought of Herb Powell when Homer adopted the pseudonym of Max Powers.

You know one thing I really appreciate about your style is how little "junk" there is. You set out what you're going to explain, you explain it, done. No gimmicks, no "clickbait" or other filler, it's all straight and to the point. It's weirdly refreshing.

Bart was right all along in his assessment of Herb. Just not in the way he meant it. *"Bastard-Bastard. Bastard-Bastard. Bastard-Bastard."*

"Hey Herb, we're going to Joey Jo-Jo's"

this is th 8th video of yours ive watched, awesome content!

I figure that once people realized the baby translator was a fraud they sued Herb into oblivion.

What's amusing is that Two Dimes was practically written just so the team could give Herb a happy ending, and yet the DVD commentary and phone gag afterwards implies they had a similar realization that "Wait a minute? Herb's actually a jerk!". :P It's almost a funny in-joke, that they made such a charismatic and emotionally manipulative character that he fooled everyone, even THE WRITERS THEMSELVES, into not only giving him a bail out, but believing that they OWED him one.

In defence of Herb not contacting any of the family after losing everything I can absolutely sympathise with that inaction. Like you said, Herb is a deeply unhappy person and unless you've been through depression yourself you have no idea how hard it can be to bring yourself to contact people when you're at a low point, even if you really want to. And if you ask me someone THAT lonely throughout their life experiencing such a calamitous loss and living just to survive... Yeah, I doubt I'd be able to do it either. He's still kind of a douchebag though, not defending everything he did.

Man,i really miss this character. I really liked him (especially since he was a missing part of Homer's youth) It sucks how criminally underused he became throughout the show's course :(

Bro your information is legit things ive always thought about and wondered if anybody thought the same glad i found your channel

You know, I bet they could make a really good episode where he actually does get called out on the way he uses people. But instead of centring it on the relationship between Herb and Homer, it might be fun to have his main interaction be with another Simpson - I'm thinking Marge.

No one to blame himself Homer warned him twice

I like the idea of calling the obligatory defence section "Playing Flander's Advicate" seeing as Ned has portrayed the devil

Make more videos like this. This was extremely entertaining

Great analysis - one of your best I was about to say all the more impressive given the lack of source material, but actually maybe that helped - minus a couple of throwaway jokes in the later seasons, all the material we have about him is from a cohesive story-driven two episode arc, perhaps its easy to get a sense of a character's drivers and personality when it isn't muddied by twenty+ years of subtle changes to suit whatever the story demands on a given day

It makes sense that he treats every interaction as transactional when you consider that his very existence is due to one transactional interaction

Great video! I would love to see the character return to discuss these exact issues. 😁

the video buffering right when you said "This is Herb Powell, he sucks" was the most perfect thing ever to me lol

Herb should’ve considered professional boxing. He drops Homer with one punch when we know that even Drederick Tatum couldn’t take him off his feet

In that simpsons comics issue, where they parody Carl barks stories there’s throwaway line, that Herb sold his title of “uncle” to mr Burns. In exchange of “charitable donation”. I always thought this was very cruel joke, but come to think about it… man, those writers… they really did understand these characters.

TBF Danny DeVito is quite the perfect voice actor for Homer’s twin brother.

I was always kind of surprised that no one wanted to buy a Homer. They were expensive, but you'd never have to listen to your kids arguing in the backseat. In all seriousness, I think Herb has a fairly complex background and he's suffering something a lot of people end up suffering. He grew up poor, he tells us that, and he worked his way through a business degree at a prestigious university. He clawed his way up in a sketchy field being abandoned by its old money managers, and he ended up hiring a bunch of people who didn't take him seriously. He has exactly one employee who tries to tell him this is all a really bad idea, the rest of them just roll their eyes, smile, and get on with it, because what does Herb know? He's just a janitor really. And I could forgive a lot of sins for that, you know, I could, if he hadn't decided to rope his little brother into it and make him a scapegoat. It wasn't even to save face, he just needed to be able to live with himself after his company failed. Then he shows up on Homer's front porch to ask for help, and he cold clocks him? REALLY? What an absolute turd.

Homer's car is oddly one of the few times Homer is 0% at fault for the bad thing that happened in the episode. All Homer did was try to get his brother better, Herb was the one who tried to use Homer to save his company. And then a year later he mooches off of Homer and uses Homer's baby to make money. Homer learns he has a brother and sees family, Herb learns he has a brother and sees dollar signs.

I know it's written for laughs and comedy and "It's not that deep" but if we are deep diving here. But good point at the 3 minute mark. The entire design process phasing of the homer mobile... The fact Herb was just as surprised and shocked as everyone else to see the prototype reveal means that he just wandered off after yelling at his staff to let homer do whatever, and never came back to check on the progress, was never curious or excited about what his brother was up to genuinely business acumen aside, and never came back to check on homer to see if they were silencing his input again. Literally he failed himself by failing homer as a brother, a mentor, an equal, and a better all at the same time. That and even if you were faltering and flailing in the business- You realistically wouldn't immediately start production on a thing you just revealed, it's a protototype at a show, and you could easily dismiss it as a miscommunication or an internal prank/joke/placeholder or spin it with some good old fashioned apple "Reality Distortion field" marketing... Herb was a bad PR frontman and business man, full stop. That and if that is all it takes to ruin a company, there would be no companies left as I can name a dozen that have had a disastrous product launch (Not even a REVEAL). And on a more directly related analogy like car recalls or flopped butt of joke models in the auto indirestly, or things like "Oopsie doopsie" type automotive recalls in the past decade like the infamous stuck brakes issue as well. And as far as ugly or tacky or who would ever prototypes- Do you remember the early to mid 2000s, aka the age of the white background CGI render product and proof of concept? Where every other leaked source or official company was showing a new revolutionary made up "MAYBE ONE DAY!" Devices like random handheld games and weird looking cars that would never work in practice. And how we were by the end of it all bored to tears of the theoretical future without a single one of those things coming to pass? Yeah. Every company that got too excited about their graphics design department getting "Good computers" is still alive and kicking turns out. TL;DR Herb Sucks and would get rinsed by anyone with a fleeting interest in marketing or economy.

Excellent analysis as always Jims!

I've just realised that you've been doing these Simpsons videos for 11 years now. I've really enjoyed this series, keep going Jim!

I think “Maude sucks”, “Sanjay sucks”, or “the lovejoys suck” would be a great series

I think another glaring point is that upon bankruptsy in the first episode, Herb leaves but seems to be fairly stable, but by the next episode he is a freaking hobo. I doubt the Simpsons would have just let him walk off if he literally didn't have any financial support when they last saw him, which implied Herb, a so called self made man who worked his way to the top scrubbing toilets, couldn't even hold a basic living and actually exacerbated his already bad position in between that time to the point he's living on the streets, again all while claiming everything befallen him is down to Homer. I mean it fits, all the hobos seem to be telling stories denying how they screwed themselves over. ("I said I'll fix the logo, put Mickey's pants back on. Some guys you just can't reason with.")

I wanted an episode that placed Homer in the middle of a battle between Herb Powell's corporate ventures and Mona Simpson's protest against Herb's company

I was just watching the golden age video, because I thought I haven’t watched a real jims video in a while. Then I got a notification for this!

6:36 "homer's brother in law"?

Herb's downfall was inevitable. Homer just sped it up a little.

one of your best breakdown videos yet. I had never looked at Herb Powell that way, as a flawed individual who reached out to family to fix his fortune, and then when that didn't magically happen, he took that as a sign that he was too 'nice', and went back to blaming Homer and seeing them as purely transactional again. Perhaps if something had happened like Bat nearly died because of his company, he'd be forced to weigh up what family really means.

A neat detail is that the interior of Herb's mansion resembles a room with a high arched ceiling in the Edsel Ford mansion.

Disney should bring herb back, and make it so herb is ceo of Disney now

I was always confused how Homer's car bankrupted the company for $82,000. Like, how did Herb only have that much in the company?

The main reason he sucks: banking your entire company's success on the ideas of a single man who has no experience in the business world and neither with cars. As stupid as Homer might be, Herb should have known better. That was a moronic idea from the beginning, and blaming Homer for it, even though Herb is literally the one person in charge who could have axed the idea at any point, was even stupider. Good will doesn't make for good business, experience does. Homer only has the former, Herb has the latter. Herb was an idiot for relying on Homer too much.

Dang back to back on this man

Herb losing his fortune was not Homer's fault. It was he who left Homer in charge of that project.

thank you! the herb episodes always annoyed me. they make it clear that his company is already losing the majority of his market share to overseas companies when homer finds him. he then forces an unwilliing idiot (who still has more self-awareness and common sense than he does, apparently) into a pivotal role that will make or break the company, ignores everyone warning him not to, and when things collapse, he becomes (more of) an abusive, manipulative bully, something he is then unequivocably rewarded for at the end of the second episode. "but aww, they hugged at the end!" no. just no. this is not a happy ending. this is a physically and emotionally abusive person being rewarded for their awful behavior with more wealth. cartoons don't have to have lessons, but that doesn't mean i won't raise an eyebrow when they actively showcase bad lessons in a show that plenty of kids are going to watch.

Now that you've done a video on Herb, I hope you get to one on Disco Stew.

With the show going back to the early stuff lately, like the bowling episode, I could imagine a return of Herb that recontextualizes him to be more in line with this pov.

I personally don’t see Herb as a terrible character. However this video was very delightful and I can see the potential in doing more videos like this. I liked the maybe section a lot. You obviously could tell from your comments section that both episodes have fans who like them including the sequel. The first episode is still the best. The Baby translator is indeed a very strange device but I totally believe that such a thing could exist in the Simpsons world. Herb definitely has some sweet moments with Bart and Lisa. I genuinely feel like “Uncy Herb” represents the hidden inner sweet guy who actually wants to reconnect with unknown family members. I would be very happy to see more videos like this. There are definitely some other characters who could use this kind of analysis. There are also some characters who also appear in only a couple episodes that could use more attention. I think that you could also try doing a “Ruth Powers Rocks” video. Her episodes were really cool and she has a big fan base!

I think the sequel episode makes him way more dislikable than the first. Like he has flaws that lead to his downfall in his debut episode but atleast I can see why you would like his character (Danny Devito’s voice REALLY helps). However, in the sequel episode he always felt off to me.

The knocker on the Simpson family home's front door is so weird.

@Therealjims Can you please do an analysis of the Mr. Sparkle episode?

Unkie Herb rocks!!! He needs to return!!! Just sad we haven't seen him since season 3....😢

I'm going to like this ideas for simpsons' characters you don't like getting a "spot light" for why you do not like them