“Hurry, Charley, there is not much time.” – Rainier Wolfcastle
“I ain’t goin’ nowhere. I’ve been in this square fer near thirty seasons, and I ain’t a leavin’ now. Aaaahhhh!” – Not Charley Weaver
“He’s dead now.” – Homer Simpson
Without drawing too broad a conclusion from just one example, there aren’t many clearer comparisons for how the show’s sense of humor deteriorated than to look at the two times they poked fun at The Hollywood Squares, first in Season 4’s masterful “Krusty Gets Kancelled”, and then again in Season 11’s pathetic “Hello Gutter, Hello Fadder”. What makes these two so revealing isn’t just the way Season 11 did a rote copy and paste job from Season 4, it’s also the way the two episodes make use of Homer.
First, though, remember what The Hollywood Squares is. Tic-tac-toe with minor or fading celebrities has been around, on and off, since the 1960s. As you’d expect, Wikipedia has an entertainingly thorough article on it, including exhaustive write ups of all four (4!) times it’s been resurrected from cancellation. But through all its iterations, including the new one that’s built around rappers, the basic concept has remained the same.
Pimpin’ ain’t easy. (Image shamelessly yoinked from here.)
It’s a show that’s cheap to produce and cheap to market because it relies on cobbling together the renown of nine low wattage and low pay stars to take the place of one big, expensive star. Given the public’s insatiable appetite for famous people (however generously defined) and the entertainment industry’s constant bestowing of mild fame on new people (as well as pushing previously big celebrities further down its guest lists), the show’s durability is no surprise.
Any institution that sticks around that long will eventually become ripe for parody, but The Hollywood Squares was born ripe. Its entire reason for existing is to wring a few coins from the leftover scrapings at the bottom of the fame barrel; taste, thought, and embarrassment be damned. Worse, not only is it trashy entertainment; it isn’t even popular trashy entertainment. After once being a hit network show, it now bounces around as cable and syndication filler, just another undistinguished part of the background noise of television. There’s a reason that all the versions are big on scripted jokes and having everyone over-laugh at them: literally none of the “celebrities” really want to be there. That’s pretty sad when you think about it, and distracting the audience from that fact is vital to the show’s appeal.
“Live from Springfield Harbor, where the sewage meets the sand!”
The Simpsons fully understood that inherent patheticness, which is why the show itself is the target of the jokes. Zombie Simpsons, which “Hello Gutter, Hello Fadder” epitomizes, can’t be bothered with that much thought, so they make Homer acting like a dick the focus of their attempt. For example, consider the way each handles the fact that The Hollywood Squares writes jokes for the celebrities who are supposedly just hanging out and being super nice and approachable.
On Zombie Simpsons, Homer just holds up two pieces of paper and asks which one he reads from. It’s a semi-clever way to acknowledge that the whole thing is a sad farce, but it’s just telling the audience what’s going on instead of showing us by making an actual joke. On The Simpsons, Kent Brockman and Rainier Wolfcastle botch the same idea:
Brockman: Oh, Rainier Wolfcastle, star of McBain and the upcoming film ‘Help, My Son Is a Nerd’.
Wolfcastle: My son returns from a fancy East Coast college, and I’m horrified to find he’s a nerd.
Brockman: Ha ha ha ha, I’m laughing already.
Wolfcastle: It’s not a comedy.
Not only is this yet another multi-layer gag where the setups are just as funny as the punchlines, but it perfectly illustrates how depressingly lame the whole ‘Hollywood Squares’ idea really is. Brockman and Wolfcastle are following the joke-laugh-answer formula exactly, but they’re so apathetic toward what they’re doing that they can’t even accomplish a simple thing like mindlessly plugging Wolfcastle’s hilariously terrible movie. This is what The Hollywood Squares actually is: bored entertainers phoning it in because they’d rather be doing almost anything else.
By contrast, when Homer shows up to the show in Season 11, he gets in a fight with Ron Howard (which he’d already done just one season earlier), and is actually pitied by him and Kent Brockman:
Brockman: We’ve got to stop putting these flavors of the month on.
Homer: Flavor of the month? Me?
Howard: Yeah, Homer, you can’t just ride one accomplishment forever.
Homer acting out and other characters responding to him is the only thing that’s going on. The show itself is assumed to be something decent and worthwhile that Homer is ruining with his brutish behavior. It’s one note comedy compared to the symphony of ideas and jokes in “Krusty Gets Kancelled”, but that’s only the half of it.
In Season 4, Homer isn’t involved in the show; he’s watching it. This is crucial because it perfectly illustrates just how demeaning The Hollywood Squares really is. He and Bart are exactly the kind of viewer the lowest rung of television is pitched at: bored flyover state residents who tune in to leer at the last glimmers of fame. That he is their audience is part of what’s so humiliating about the show. Entertainers who were once at or near the top of their game have been reduced to trading on whatever recognition they have for a (probably not very generous) paycheck. Worst of all, they have been reduced from stars to replaceable cogs so easily dismissed that when one of them is crushed (and presumably killed) by a tidal wave, their target audience thinks only to laugh.
“Krusty Gets Kancelled” sees through the forced laughter and glittering lights to the cheap sets and career desperation because it understands that no one has ever gotten into show business to be on The Hollywood Squares. “Hello Gutter, Hello Fadder”, on the other hand, buys into all that lame self promotion that The Hollywood Squares uses to distract the audience from just how sad it really is.
charliesweatpants.com
(The crotch really does wear out too fast.)
Dead Homer Society 
Why was Homer there anyway? Unlike Season 4 there is absolutely no point to show that whole scene except for pointing out that he’s a low grade celebrity now (and even then it doesn’t quite seem like it). When Howard shows up the whole setup turns into what eventually became a “celebrity” cameo in his/her natural habitat, according to Zombie Simpsons. The whole episode is not so bad itself actually, we don’t see anyone bond with Maggie so often.
And why were Itchy and Scratchy there? I suppose they were just people in costumes, but it’s really hard to tell when you give them their regular voices.
And when their mouths move properly too.
Ironic how Howard says “Yeah, Homer, you can’t just ride one accomplishment forever”, when… isn’t that the point of Hollywood Squares? Nearly-forgotten celebrities trying to squeeze out a little more fame from the rolled-up toothpaste tube of their career? Great summary of how ZS completely gave up on the whole “satire” thing.
I love the “He’s dead now!” line.
I think they tried to parody what you say with that line, kinda like someone who’s only good at one thing saying “You can’t just be good at only one thing”. Prob is, as soon as humor becomes bidirectional (i.e. too direct in your face), it’s only worth a chuckle and is quick forgotten.
I enjoy most of the Simpsons reviews there but the implied contempt the authors have for “bored flyover state residents who tune in to leer at the last glimmers of fame” is pretty disgusting. So people who live in the mid-west are basically Homer and Bart Simpson?
I meant this from the point of view of the entertainment industry, not my point of view:
“He and Bart are exactly the kind of viewer the lowest rung of television is pitched at: bored flyover state residents who tune in to leer at the last glimmers of fame. That he is their audience is part of what’s so humiliating about the show.”
The people who make the crummy, fame desperate game show look down on the likes of Homer and Bart; therefore it’s humiliating from their perspective that their target audience is people like the Simpsons (wherever they may live). It’s their point of view, not mine. Didn’t mean to be confusing there, sorry.