Season 2 of The Simpsons was a proper roller-coaster of emotion. There are multiple episodes involving characters entering into the Simpsons' lives, forging some meaningful connection with one or more of the family and then having to painfully part ways by the story's end. Karl of "Simpson and Delilah" and Mr Bergstrom of "Lisa's Substitute" each compete for the most heartbreaking of these inevitable goodbyes (I would give the edge to Bergstrom, even if I'm otherwise a card-carrying Karl devotee). The gruesomest, most gut-churning goodbye, however - oh boy, that's no competition. The title goes to "Oh Brother, Where Art Thou?" (episode 7F16), which first aired February 21st 1991. In this one, Abe suffers a mild heart attack and, rattled by his perceived brush with his own mortality, decides to share with Homer a family secret he's kept hidden from him all these years - he is not actually Abe's first child. Before he settled down with Mona, Abe had a one night stand with a hooker he encountered at a carnival, and their union was a fruitful one. Since neither parent wanted to take responsibility for the baby, they left him with the Shelbyville Orphanage, and to this day Abe has no idea what became of him. Homer is a lot more driven to uncover the answer, and eventually locates his half-brother living in Detroit, Michigan. He discovers that the man, one Herbert Powell (guest voice of Danny DeVito), has done extremely well for himself, and is now the wealthy CEO of a major automobile manufacturer, Powell Motors. Herb, though, has a very different perspective. As he sees it, Homer has the one thing he doesn't, which is a family, and that makes Homer by far the richer man. It sounds like such a sweet and wholesome scenario, but good lord is it headed for disaster.
Here's an observation I'm not sure I've seen anybody make about Herb, but which with hindsight strikes me as significant - he is, in many respects, a proto-Frank Grimes (see "Homer's Enemy" of Season 8). When you look at it, their backstories are eerily similar. Both of them were abandoned by their biological parents. Both of them are self-made men left battered and embittered by a system where everything seemed to be weighted against them but where others got a free ride through nepotism or sheer dumb luck (there is a lot of overlap between Herb's tirade during the Persephone pitch meeting and Frank's tirade on Homer's doorstep). Both their lives were thoroughly rocked on intersecting with Homer's - one of them was overwhelmed by his love for Homer, the other by his hate, but that made very little difference to how things worked out for them in practice; they both crashed and horrendously burned. Where they diverge is that Herb allowed himself to become blinkered to what Grimes could see only too clearly - that Homer was dangerous and not to be trusted. If Grimes' story was a tragic bearing out of the adage that a sane person to an insane society must appear insane, then Herb's is a cautionary tale on the pitfalls of not being able to tell the difference. His blunder was in mistaking the society he inhabited for an insane one, and Homer's intrusion as the overdue voice of reason, instead of the ticking time bomb it turns out to be. Truthfully, Herb is a much more cursed individual than was Grimes. Grimes at least had an easy enough time figuring out where he stood. He was an outlander in the Simpsons universe, ill-equipped to understand, much less survive its mind-boggling absurdities, and his suffering there was made mercifully brief. The thing about Herb is that he actually does belong in Homer's world. He has Homer's face. He's a man begot by an insane world who had the tremendous fortune of being exiled and raised among the sane, but who always felt out of step there, as though he didn't fit in. "Oh Brother, Where Art Thou?" sees the Simpsons heading to Detroit for an induction into Herb's lavish lifestyle, but it's really Herb who's coming home, gaining the long-awaited opportunity to reconnect with his roots and discover who he really is. Of course, he ultimately realises that he was better off not knowing, but by then it's too late. His hard-earned fortune and reputation are gone, and he's been cut down to Homer's miserable level. Lisa phrases it explicitly, for the benefit of anyone who wasn't paying attention: "His life was an unbridled success until he found out he was a Simpson."
"Homer's Enemy" is a considerably darker slab of Simpsons life than "Oh Brother Where Art Thou?", having caught the series at a meaner, more jaded point in its run. Herb and Grimes are each brutally destroyed by their fixations with Homer, but Grimes is the only one to whom this applies literally. Which doesn't negate just how unflinchingly bleak the ending of "Oh Brother, Where Art Thou?" is. Frankly, it still has the power to deliver one heck of a searing gut-punch. As noted, endings that didn't shy away from exploring painful truths were not a rarity throughout Season 2. "Simpson and Delilah" ended with Homer losing his promotion along with his hair, because nobody would take the bald man seriously. "Bart Gets an F" had Bart putting his all into studying for a history exam and still flunking by one mark. Bergstrom abandoned Lisa for Capitol City at the end of "Lisa's Substitute", leaving her with the written reminder that she, much like Herb, would forever be a Simpson. "Oh Brother, Where Art Thou?" goes a step further than them all, in offering no redemption, no light at the end of the tunnel. Herb disowns Homer completely, and the family are sent packing back to Springfield. Roll credits. There's a small moment at the very end where Bart says something to Homer that brightens the mood slightly, but it feels like deliberately meagre consolation compared to the absolute onslaught of bitterness that's preceded it. It must have left someone at Simpsons HQ with a guilty conscience, for they wasted little time in creating a sequel episode purposely designed to offset the sourness of this one. Rounding off the third season was "Brother, Can You Spare Two Dimes?", which saw Herb recover from his financial ruin and ultimately re-accept Homer as his brother. It's pretty clear, however, that things are never going to be the same between them. Herb has seen Homer for what he is, and there's no going back on that.
Simply put, I adore Herb Powell. I'd rank him alongside Jacques and Karl as one of those early presences who helped the fledgling world of the Simpsons feel immediately richer and more alive, but who was sadly forgotten as the series progressed (it still seems such an amazing fluke that Sideshow Bob didn't go the same way, but then I guess there was always a vacant spot for a recurring villain). One of the major things that made all of those characters stand out was that they were voiced with such flair and passion by their respective actors, and Herb was certainly no exception. Danny DeVito (like A. Brooks, he was a good buddy of series producer James L. Brooks) was the perfect choice to supply Herb's vocals. The obvious, predictable route would have been to have had Dan Castellaneta voice him, doing a slight variation on his Homer voice (a la all those random Simpson relatives in Season 9's "Lisa The Simpson"), to emphasise that the guy is effectively Homer from a parallel reality. Thankfully, they were able to think outside the box. Giving Herb a strong and distinctive voice, utterly apart from his brother's, really helped cement him as a character in his own right. It would have been so easy for him to have played as a gimmick character, or as a hollow plot contrivance; instead he feels like a fleshed out, legitimate part of the series' world-building. You could argue that DeVito was a more recognisable "celebrity voice" than other instances of early Simpsons guest casting, but he embodies the part so well, nailing all facets of Herb's personality - the warm, spunky side, the broken, vulnerable side and the aggressive, hectoring side. Because that's the other thing that makes Herb such an enduring character. The dude's got layers. Which side of his nature you get might depend on the angle you walked in from. He's really not that nice of a guy. He's prone to some pretty vicious mood swings and is brimming with contempt for anyone he considers beneath him (more so than Frank Grimes, honestly). And yet he is at all times sympathetic. You never lose sight of that little lost kid who's felt disconnected his entire life and is overwhelmed with joy on being reunited with the blood relations he erroneously believes are going to fill all his emotional holes. Being so in touch with his inner child, Herb bonds beautifully with the Simpsons children and wants nothing more than to give them the time of their lives. He's the kind of guy it might be fun to have as your actual uncle, but an absolute nightmare to have as your employer.
"Oh Brother, Where Art Thou?" begins with Abe and Jasper watching the latest Rainier Wolfcastle flick at the Aztec Theater, and an argument with a young usher (a sort of evolutionary ancestor to the Squeaky-Voiced Teen, but with way too much pluck) about the tacked on romantic subplot triggers Abe's heart attack. The early McBain skits are always fascinating to watch because you can see the seeds in these things for what later became The Critic (Al Jean and Mike Reiss have no writing credits for this episode, but this one scene has their fingerprints all over it). At this point, there was also enough of a contrast between McBain's overblown fictitious world and what could reasonably happen within the Simpsons' reality (a barrier that would be all but obliterated in the space of two seasons). As timelessly hilarious as McBain's Hollywood bombast might be, I'd be curious to know just how frequently he shows up in the newer Simpsons episodes, because as a reference he seems almost as archaic now as the Happy Little Elves. Wolfcastle was most obviously conceived as a pastiche of Arnold Schwarzenegger, but he was spoofing a broad number of macho movie stars who were big at the time - Sylvester Stallone, Steven Seagal, Jean-Claude Van Damme, Bruce Willis, etc. The kind of action flicks those guys made are nowhere near as prolific now as they were at the dawn of the 1990s, with superhero movies having replaced them as the predominant Hollywood action model (and the Simpsons, thanks to Disney, having become shills for such things - there's no way Jay Sherman would break bread with these guys now [1]).
Abe has only a minor role in "Oh Brother, Where Art Thou?", but this feels like his most revealing appearance thus far, and it doesn't reflect at all well on him. Even without any flashbacks detailing how he parented the young Homer, we get significant illumination on the kind of father he was, and the extent to which Homer may be the reflection of a psychologically abusive upbringing. Homer is moved to tears by his father's story, because he interprets it to mean that Abe must have wanted him, if he did not offload him as he did Herb. "Interesting theory," Abe murmurs. Later, when Abe is brought up to speed on the man Herb became, he discreetly mutters, "I kept the wrong one." It never occurs to Abe that he was fated to get stuck with the "wrong one" either way - if he had taken responsibility for his first born, then it's doubtful Herb would have ascended as far in life as he did. A rearing by Abe would unquestionably have hurt Herb, and yet it might actually have helped Homer. The presence of a third individual would have altered the dynamics of their household and made him less of an obvious target for Abe's bullying. Then again, based on what we're shown in this episode, if Abe had kept Herb, there's every chance that things might not have worked out between him and Homer's mother. "Oh Brother, Where Art Thou?" takes massive strides in exploring how dynamics worked on Homer's side of the family, establishing not only the existence of Herb but also what a womanizing sleaze Abe apparently was in his "youth" (he doesn't actually look that young in the flashback sequence) and giving us our first glimpse of the elusive Mona Simpson. Here, she's voiced by Maggie Roswell, and seems as eager to sweep Herb under the rug as Abe, making him promise never to tell Homer of his illegitimate brother (something Abe only remembers once he's already told Homer the full story). This feels at odds with how Mona was later characterised in "Mother Simpson" - the Mona voiced by Glenn Close was a conspicuously more liberal woman, and I suspect she'd more likely have encouraged the relationship than outright denied it. But then having to retroactively factor in the developments of "Mother Simpson" inevitably casts an awkward light on the entire set-up of "Oh Brother, Where Art Thou?", since we're told there that Abe has concealed not just one but two major familial secrets from Homer. If he really believes he's on his deathbed, then when was he planning to drop the even bigger bombshell that Homer's mother has been alive this whole time? It's a dubious business, allowing your perception of an episode to be coloured by narrative events that blatantly hadn't crossed the writers' minds when first it aired (I'm going to fess up to a time when I did exactly that toward the end of this review), but it bears saying nonetheless. Whichever way you slice it, the Simpson line is a flagrantly chaotic one. Say what you will about the Bouviers, but they've clearly got a better sense of unity.
The nicest thing you can say about Abe, as portrayed in "Oh Brother, Where Art Thou?" is that he has presumably felt some remorse for his abandonment of Herb, if it's a weight he's compelled to get off his shoulders. But that's as far as his interest in absolving his guilt goes. His desire to meet with Herb is ignited only on learning how rich and successful he's become. When he gets there too late and discovers that Herb has already vacated, having lost his vast fortune thanks to Homer's idiocy, he doesn't even care to hear what happened. Of course, given that Herb has such a temper problem, and that Abe had already wronged him, you have to wonder if he'd have been as willing to roll out the welcome mat for his old man as he was for Homer. Alas, the prospective relationship between Abe and Herb will have to remain uncharted - they don't get to meet in the sequel either, not even with Herb living with the Simpsons for what must be a fairly substantial length of time. Apparently it just never crosses anyone's minds.
As Herb puts it, he's just a lonely guy, a statement that touches on three different nerves at once - his prioritisation of his career over starting a family, his having known nothing of his roots until now, and his having led a misplaced existence as a successful Simpson in the "real" world (ie: far from the cursed confines of Springfield). When he first meets the Simpsons, there's a sense of him understanding cars better than he does people (on grabbing hold of Maggie, he takes a sniff of her and comments on the "new baby smell"). Although I do have this one major question regarding Herb's loneliness - what are we to assume happened between him and his adopted family? Mr and Mrs Powell may not have been his biological parents, but they did take him in and raise him as their own, so does he feel no sense of kinship with them at all? Nominally, he continues to identify with them, but they're otherwise out of the picture - Herb's sole reference to this adopted parents is in indicating that they didn't pay for his Harvard education. Jeff Martin's script never establishes what, if any, relationship they still have, nor does it attempt to explore how Herb's feelings of belonging and identification as a Powell might impact his relating to the Simpsons, and vice versa. From a narrative perspective, that's fair enough - this is meant to be focussed on the Simpsons' perspective, and bringing the Powells in might have made the arrangement more complicated than we perhaps have time for in 22 minutes. It is, however, a question that becomes even more pressing with "Brother, Can You Spare Two Dimes?", when we rejoin Herb to find him sleeping on the streets, and it's pretty danged harrowing to think that no one in his adopted family stepped in to prevent this. Are his adopted parents dead? Did they have some kind of cataclysmic falling out? There is, presumably, a story to be had there that's as emotionally devastating as anything we see at the end of "Oh Brother, Where Art Thou?"
The obvious answer is that Herb's adopted family don't actually exist, because nobody in the writers' room cared to give him one - the unseen Mr and Mrs Powell were a plot device to get him well away from the Simpsons, after which their purpose was served. We did, however, get a glimpse of them in the tie-in book The Simpsons Uncensored Family Album, published in 1991. At the front of the book is a family tree detailing the Simpsons' genealogy (with one for the Bouviers at the back), in which the Powells are included. Ordinarily, I would be heavily guarded against the idea of treating material introduced exclusively in these tie-in books as canon - the same book also indicates that Mr Burns is a distant relation of the Simpsons clan, and I'd be very surprised if that was ever supported in the series proper. But since there's currently nothing in the series to contradict the details of Herb's adoption, and it is all we have to go on, in this particular instance I don't see the harm. According to the Uncensored Family Album, Herb's adoptive parents were named Edward and Mililani, and they had three biological daughters, Coco, Wanda and Carla. If we read between the lines, we might conclude that the Powells adopted Herb because they had all those daughters and wanted a son. All the same, having to factor so many sisters into Herb's backstory makes it all the more depressing, since it adds to the tally of relationships in his life that have potentially broken down. I'm guessing Herb doesn't have much contact with his sisters either - not only is he seemingly unable to turn to them after the events of "Oh Brother, Where Art Thou?", it's evident in the episode itself that Herb has never experienced being an uncle before and that having this relationship is novel and exciting to him. It's not a given, I know, but with that many sisters you'd think that at least one of them might have had kids of her own by now? The series is unlikely ever to touch on this stuff, so I guess it's over to you fanfic writers to decide.
(You'll notice that Mona Simpson's name is here given as Penelope Olsen - which actually was one of the aliases she used in "Mother Simpson", so we can't entirely discount this thing. Not sure how we're to account for Jackie Bouvier's name being given as Ingrid, though - outside of the obvious explanation that the series and book writers were each just making shit up as they went along.)
The Powells aren't the only family who've got a patently fascinating backstory that's casually brushed aside. "Oh Brother, Where Art Thou?" also sees the introduction of a running gag regarding Dr Hibbert and his multiple long-lost siblings, as Homer receives tip-offs from a man who is conspicuously Hibbert's twin, separated at birth. Actually, I'm not sure this went far enough to be considered a "running gag", but I find it hard to believe that the writers didn't have this episode in mind when they later insinuated that Hibbert and Bleeding Gums Murphy were also unwitting brothers, in "Round Springfield" of Season 6. (It's a callback that makes Murphy's solitary passing all the more tragic, since you're aware that he's actually got two brothers, and neither knows that their sibling is dead.)
The other major question regarding Herb concerns the extent to which he brings his ruination on himself. He hits on the idea of having Homer design a car for the average consumer, having noted how drastically Homer's expectations diverge from the company's assumptions, then takes zero interest in how the project is shaping up, failing to so much as look at the prototype until the fateful public unveiling. We can see the impending disaster from a mile away, with every one of
Homer's increasingly dreadful demands taking us a step closer to the
absolute car wreck (in more ways than one) gearing up to happen. Still, Herb remains too intrinsically sympathetic a character for us to enjoy
seeing him get what's all but inevitable. His downfall is again threefold, a perfect storm brewing from his misplaced faith in his brother, his total disdain for his workforce, and how much he's relishing getting to spend time with his nieces and nephew. He fails to keep an eye on what Homer's up to because he'd rather be hanging out at the zoo, bribing the staff to let the kids go into the exhibits and get dangerously close to the penguins. (In the meantime, Marge doesn't have a lot to do, although the script incorporates one of my all-time favourite Marge-isms, when Herb asks for a little background information on herself. She states that she and Homer were married and had three children, then admits upfront that she's already told him everything worth knowing.) He also doesn't care to listen to his employees' misgivings, having already decided that it's himself and his brother against a world that makes little sense. His contempt for his underlings is so off the charts that in one scene he flaunts it by coercing one into saying the exact opposite of what he thinks of Homer, on speaker phone so that Bart and Lisa can hear, giving them a false impression of their father's prowess and fortifying his own drunken sensation of at long last cutting through the bullshit he's had to deal with every day of his pre-Homer existence. He gleefully ignores all the warning signs, including the implicit warnings in Marge's repeatedly-voiced concern about the likelihood of spoiling the children. Herb is intent on ruthlessly indulging his inner child, giving Homer leeway to do exactly the same. The car that emerges is a brutal wake-up call that what they both needed to do was grow the hell up.
It seems significant that the grotesque set of wheels Homer conceives would also bear his name, since the car is a manifestation of everything warped and preposterous about his id. It lays horrifically bare to Herb not merely what kind of man he's invited into his life, and into his business, but what kind of man he's been all along. He's thrown his lot in with both Homers, and now he's going down with them. Powell Motors is bankrupted by the project, and Herb is swiftly exiled from his luxurious home. It's in the episode's tart resolution that The Simpsons was able to reaffirm why it was such a refreshing alternative to the other sitcoms of its era. In a more conventional sitcom, a car as cartoonishly abominable as the Homer would never have come to fruition, period. But in the penultimate scene, when Homer suggests that maybe it would have been better if he'd never come to Herb, a conventional series would have likely indulged the response Homer is blatantly reaching for - that Herb is happier just for knowing who his family is, and that the money, house and business he's lost were never that important by comparison. Instead, Homer finds himself on the receiving end of one of Herb's tirades - he tells Homer that of course he would have been better off if he'd never come into his life, and that as far as he's concerned he has no brother. Is this perhaps a mite unfair of Herb, given that he surely has to take some responsibility for giving Homer full reign over his castle in the first place? Yeah, but you have to keep in mind that for Herb, Homer is an extension of himself - the man he could have been, and the man he could still become. He now sees this is no good thing, and is determined to put as much distance between himself and his twisted reflection as possible. And he's not the only one. Homer is denounced twice over, when Abe shows up in a taxi, eager to meet his millionaire first-born, only to find that the ship has already sailed and submerged. Homer offers Abe a ride home, promising to fill him in on the sorry details along the way, but Abe isn't even prepared to share a journey with the son he views as an eternal screw-up, getting back into the taxi and finding his own way out of the situation. As the family leave Michigan, Homer gets a morsel of consolation from Bart, who assures his father that he thought the car was cool. Homer's father and brother might each see him as a reflection of the very worst of themselves and project their self-loathing onto him, but there is a thread of hope in that Bart can look to his father's vision and see something in it that was sincere, spontaneous and fun (although Bart possibly wasn't aware what kinds of unpleasant features Homer was wanting installed to keep his kids under control [2]). It's a meagre alleviation, but we can see how it means the world to Homer. For as cursed and chaotic as his lineage may be, we see a little bit of that Simpsons solidarity come through, at least among our central unit.
It's here that I do have to backtrack on something I said a few years ago, in my review of "Old Money". Having that episode follow on so soon after "Oh Brother" still doesn't sit well with me, because Herb and his having lost everything is going to be fresh on our minds as we watch Abe potter over his newfound fortune and which needy soul he should be helping. But to be totally fair, it's actually not clear from the ending of "Oh Brother" that Herb is headed for quite the level of destitution we find him in in "Brother, Can You Spare Two Dimes?" For all we know, he's going back to the Powells, or to stay with a contact he's made in the automobile industry. His becoming a down-and-out was an invention purely of the sequel, along with the specific details of his eating cheese out of discarded pizza boxes and using rats for pillows, and that was still a year and a half away. The intended implication of Martin's script was, I suspect, that Homer had brought Herb down to his own level; the sequel was written by John Swartzwelder, who according to the DVD commentary has this thing about derelicts, so no surprise that's where he'd stick Herb. There's ambiguity as to whether "Old Money" was consciously written to follow on from "Oh Brother", with the knowledge that Abe has two sons (he tells Bea he has one, but later makes reference to his having had multiple children) - either way, I think I'm justified in having Herb in mind as I watch it, but I'll concede that I shouldn't let my perception of the story be so heavily coloured by an episode that didn't even exist when it aired. Most of my feelings on "Old Money" still stand, but I'll retract the all-caps rant at the end of that write-up.
As for Herb, he is fundamentally a survivor, and there'll be more to say about him when I cover "Brother, Can You Spare Two Dimes?" He's also fundamentally a misfit, in that his genetics and his upbringing will forever be at odds. At the end of "Oh Brother, Where Art Thou?", when he's kicked out of his Detroit-based empire, he knows that his real place is with the Simpsons, and that the logical thing to do would be to return to Springfield with them and pick up the life that was once ordained for him. At the same time, he was raised among normal society, and he is too much of a normie to be capable of assimilating into their world - he angrily rejects his kinship with the Simpsons and boards a bus that will take him far away from them, even if that means resigning himself to a life of perpetual solitude. In the end, his story might be less comparable to Frank Grimes' than to that of another character introduced in Season 8 - Hugo, Bart's Treehouse of Horror-exclusive long-lost twin brother. Dr Hibbert (who always seems to find his way into stories of this nature) described Hugo as being "too crazy for boy town, too much of a boy for crazy town - the child was an outcast." That about sums up Herb.
[1] I'm not sure if I'll ever go in-depth into my feelings on those Simpsons shorts made under Disney to promote their streaming library, but know that they are much the same as Frank Oz's on Disney's handling of The Muppets: "They're cute...I love cute things like little bunny rabbits, but I don't like pejorative cute."
[2] If I remember correctly, wasn't there a similar joke in the 1992 movie Stay Tuned? We actually got to see some of those features in action.
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