I was telling Dan/Tom that in place of doing anything productive (aside from writing a few pages of the novel here and there), I have been dealing with a rampant bout of insomnia by re-watching the first six seasons of The Simpsons (mostly via these somewhat-low-bit-rate streams). Season One is fun but uneven, and Season Two (while generally great) is still working a few things out.
By Season Three we are in the Golden Age, which, in my most honest estimation lasts from Season Three through Season Five. This is very strict, I realize. Much of Season Six is excellent, and some of my favorite episodes are in Season Seven, but by Six we have real signs of decline (The Critic cameo being foremost among them, but also the repetitive Marge storylines that start to bleed into each other)...
In any event, anywhere in Three to Five you are guaranteed a good show. Virtually every episode (except for the clip show) is worthwhile and probably has some number of memorable, definitively original Simpsons' moments...
With this as backdrop, I thought I'd give a brief run down of my five favorite supporting characters from the show:
#5 Selma Bouvier: While she often appears to simply blankly repeat the pronouncements of her more dominant twin Patty, in the episodes in which she is showcased (her ill-fated marriages to Sideshow Bob and Troy McClure, and her musings on lonesomeness in the brilliant "Selma's Choice") she is shown to be one of the most sympathetic figures in the show. The dialectic of her dependence on her sister with her desire to marry and escape her identical twindom is rather deftly handled in these particular episodes.
#4 Moe Szyslak: Moe, with his relentless threats of suicide, with his sometimes manifested homicidal rage, with his utter lack of social intelligence (most obviously in his relationships with women and his prank call demeanor)--Moe, along with Groundskeeper Willie, is the most obvious example in the show of a total social pariah who nonetheless is integrally involved in the affairs of life--it is a 'meme' going back to Dickens--but this manifestation in this medium is momentous.
#3 Principal Skinner: I refer to the pre-Tanzarian Skinner, of course, but remember the early Skinner was a really dark figure. He had horrifying flashbacks to The Nam during announcements on the regular, he was a pathetic underling to Chalmers (later they seemed to become friends)... Oh yeah, and he had a relationship with Patty Bouvier... Whoops! When we got to see Skinner all Mike Bradyed out after he lost his job, that was the bomb. God I love that cat... Oh yeah, and his mother! Hilarious!
#2 Lionel Hutz: This was a really tough call. Ideally, I would present some kind of McClure/Hutz hybrid, because really, Phil Hartman was simply wonderful in both roles. But Hutz wins out because he appears in more episodes (I think) and is generally more despicable/absurd/insane ('Say hello to Miguel Sanchez!') than even fish-fetishist Troy.
#1 Charles Montgomery Burns I don't think there is a better boss figure in all of literature; sure there are the Critch family in Lawrence's Women in Love and of course the despicable Scrooge of Dickensiana... But really, Mr. Burns contains all of these traits, and so much more, from his ambiguously gay relationship with Smithers to his inability to remember his employees, to his talent for Seussian meter and lyricism, to his Yalie status, to his various incarnations as a youthful freeloader, to his Charles Foster Kane moment... Many people complained of the Simpsons Movie (which was worthless) that it featured too much Flanders and too little Burns... I could not agree more. Bravo, Monty! 'To friends he's known as Monty but to you he's Mr. Burns!'