0421 - Herb Powell

Herb first appears on screen during Homer's phone call with him, shrouded in mystery.

It is then a full three minutes before he is revealed to the gag of "he looks a bit like Homer."

The rest of the episode is Herb's story, about how he falls from his wonderful life after learning he is a Simpson. I've seen many point out how he has no real right to be angry at Homer - Herb's company's downfall is a result of his own decisions and actions, not Homer's. In some ways, this is quite realistic - a rich CEO is likely to blame everyone but himself for his own shortcomings. What's unrealistic is that he'd suffer any consequences when the ship sinks. Perhaps the most damning evidence that Herb is a Simpson is that he was not smart enough to give himself a golden parachute when his empire (seemingly very quickly) crumbled beneath him.

Herb's other major appearance is in season 3's finale, "Brother, Can You Spare Two Dimes". This is a rare sequel episode in which Herb is allowed to rebuild his fortune, because as we all know getting rich is as simple as working hard and having an idea, no other external factors are taken into account.

I think this episode was made mainly because the end of "Oh Brother, Where Art Thou?" is such a downer. The Simpsons rarely gets a chance to course correct and alter plot decisions they regret (they'd have to get pretty convoluted to resurrect Maude Flanders, for example,) but with such a minor character as Herb it's easy and crowd pleasing to reverse his misfortune. And so Herb is rich again.

Until

It's a throwaway cameo gag in season 24's "Changing of the Guardian", but it does add a little more lore to the Herb Powell story. It's not expanded upon, and Herb's other much publicised recent cameo appearance ("Bart's Birthday", season 36,) sounds like it offers little more to Herb's status (the episode is not currently available to me in the UK.)

For such an earth-shattering addition to the Simpson canon, Herb is just not that much of a presence. He is referenced in passing a few more times, such as a picture on the wall in season 16's "The Heartbroke Kid":

Or in the couch-gag for season 8's "Bart After Dark" (back row, next to Flanders):

Or in the Ducktales parody comic "Uncle Burn$" from Simpson Comics #102:

But considering he is Homer's half-brother, it's surprising that 36 years of adventures haven't found more space for Herb-related stories. The simplest explanation for this is that he is played by a major movie-star, Danny DeVito, who most likely won't have much time to semi-regularly appear on a cartoon. That said, he has been a regular on another TV show ("It's Always Sunny In Philadelphia") for almost 20 years now so WHAT GIVES DANNY??!?!?

DeVito was very busy in the 90s, both acting and directing, and The Simpsons just wasn't a big enough draw to firmly establish Herb beyond what we've outlined here, so he remains an oddly small piece of the ever expanding Simpson mythology.

This post is part of my "Every Simpsons Character Ever" series. For a list of my rules in this project, click here.