In the 20 plus years of my love affair with The Simpsons I’ve seen more memorable characters than I can possibly count.
The principle characters alone are legendary, but a show with the longevity and ability to remain relevant like The Simpsons cannot rely solely on its main players.
The Simpsons triumphs in ancillary characters, from celebrity voiced one-offs to clever cameos, and this is a major reason for the show’s continued success.
There are certain characters that stand above the rest, characters so profound that their very existence added new dimensions to a show with an already rich character library, and for this reason I wish they had far more screen-time than they were allotted.
5. Karl (Harvey Fierstein; Simpson and Delilah)
Karl was briefly Homer’s assistant and quite possibly the most astute employee the power plant has ever seen (Frank Grimes aside of course). He took the fall for Homer during a major discrepancy and was released from service.
Karl was the first best thing to ever happen to Homer with the exception of Marge. He understood the blundering everyman on a cosmic level and approached his boss with a perfect pairing of pity and respect. Having Karl steadily in the mix at the power plant, or to a lesser degree in the background, would add a hidden layer of competence to the entire operation…now that Frank Grimes is dead, of course.
4. Cecil Terwilliger (David Hyde Pierce; Brother From Another Series/Funeral For A Fiend)
The younger brother of Sideshow Bob and a criminal mastermind in his own right, Cecil was a perfect compliment to the seedy Springfield underworld. Appearing in just two episodes (and a brief cameo in the 21st season), Cecil’s character depth was cut short.
David Hyde Pierce brought the wit and snooty integrity that made Niles Crane such a beloved television character but turned the vibe significantly darker in nature. There have been limitless opportunities for Cecil to resurface, but sadly, he has not.
3. Herb Powell (Danny DeVito; Oh Brother, Where Art Though/ Brother Can you Spare Two Dimes)
He had it all then lost it all…then got it all back. The far more astute brother of Homer J. Simpson, Herb Powell, only graces us with two full episodes and a small handful of photo appearances throughout the long history of The Simpsons. The dynamic he brings is akin to the dynamic brought by any long lost Simpsons relative; we get to see another side of Homer.
Much like Homer’s mother, Herb understood his oafish brother and embraced his hair-brained schemes (to a fault). DeVito’s voice acting alone is enough to clamor for more Herb, but watching him interact with his brother, and being able to see glimpses of each other within themselves is where the real magic lies.
2. Chester Lampwick (Kirk Douglas; The Day The Violence Died/ Old Yeller-Belly)
Lampwick, the original creator of Itchy, is one of my personal favorite characters. A man who was ripped off and lived most of his life in abject poverty, eating from garbage cans and having numerous battles with Krusty and Grandpa, finally had his American dream come true by winning a lawsuit and living off of the settlement.
And by “living off the settlement” I mean “living like the Monopoly man.”
Lampwick is a profound character because he could have been another cog in the Itchy and Scratchy machine throughout the years. He only had one real episode and a cameo in another (in which it’s assumed he lost everything again – ‘Merica) but c’mon, the guy had a solid gold house and a rocket car. Surely he deserved more love just for that.
1. Larry Burns (Rodney Dangerfield; Burns, Baby, Burns)
Honestly, how could there be anyone else at number one?
The incomparable Rodney Dangerfield brought everything about his loveable loser persona and injected it into the bastard son of Monty Burns. A lost cause that once saw a blimp, Larry quickly zinged every blueblood in Springfield and drank his weight in booze.
Larry was a friend to Homer and a constant thorn in the side of Burns but he just fit so well into Springfield that it’s shocking he didn’t make another appearance.
Arguably the funniest episode of The Simpsons, there is a somber, bitter-sweetness when you see the touching tribute to the late, great Rodney Dangerfield that appears in the end credits.
