(or "Dumpy Guys Are A Tough Sell")
On paper, the ABC (and later Fox) series "The Critic" seems like it should have run for a long time. The creative team behind it shares a lot of names with the seemingly-immortal "Simpsons", it's got a pretty familiar name as the lead in Jon Lovitz, and the storytelling engine feels remarkably strong for a "workplace sitcom", especially an animated one. Sitcoms set in an office (or a TV studio) that center on the inter-personal dynamics of the (generally quirky) characters who have to work together despite their various dysfunctions, tend to reach a point where it's hard to keep finding things for them to do that aren't repetitive; the good ones, like 'Cheers', work around this problem by having a flow of guest-star and semi-regular customers to keep things fresh, while the bad ones just embrace repetition. (I'll leave it up to you to fill in the blank here with your own most-hated sitcom.)
By focusing primarily on one character, film critic Jay Sherman, "The Critic" works around this problem by expanding to his family and romantic life as well as his job, and showing all the ways those intertwine. He has to deal with an egomaniacal boss (who is wonderfully played by Charles Napier as a crazed Ted Turner), a frustrating and emotionally distant family (with the exception of his little sister, who looks to him for guidance), and the fallout from his disastrous first marriage. Each element provides fodder for one or more stories above and beyond the typical "workplace" drama, which is also present (and it helps a lot that the choice of "film critic" as job allows for plenty of gags about the entertainment industry, from brief gag movie clips to whole episodes revolving around a spat between Ebert and Siskel.)
So why, with all the talent behind it and all the opportunities available to it, did "The Critic" fail? Even a spot just in front of 'Home Improvement' couldn't help it on ABC, and even a guest appearance on "The Simpsons" couldn't save it on Fox. (And incidentally, that's not a good question to bring up to Matt Groening. Trust me on this.) What made "The Simpsons" into a huge success, and "The Critic" into an obscure cult series?
We have to consider the setting to be a culprit; unlike "The Simpsons", which takes place in a deranged vision of Anytown USA, "The Critic" sets itself in New York City and is squarely cosmopolitan. From a storytelling angle, this works great. New York becomes a character in its own right in the series, with the atmosphere of the city informing every episode in all sorts of ways that show that more than a few New Yorkers worked in the writing room. But to a non-Manhattanite (yes, we do exist!), these elements worked to exclude potential viewers instead of draw them in. It's sort of like Woody Allen's films, which work well in critics' circles but never seemed to make a ton of money in nationwide release.
A comparison to Woody Allen also brings us to the key point that made "The Critic" a tough sell; it's a self-consciously intellectual comedy about an intellectual character (how many sitcoms are about Pulitzer Prize-winners?) In a country like America, which has a long tradition of anti-intellectualism, that's a tough sell in and of itself. But more than that, "The Critic" is a comedy about failure, about a single guy who stays single due to his lack of confidence (and looks and virility and savoir faire...) Despite the seeming attractions of the concept, audiences don't tend to want to watch the lives of people who are even worse off than they are, especially not one who seems to be mired in failure. The series attempted to fix that when it moved to Fox, adding Park Overall's "Alice Tompkins" character as a love interest, but by then, the tone of the series had already been set in the minds of its potential viewers. And so Jay Sherman, like Woody Allen, remains an acquired taste on DVD instead of an enduring icon like Homer Simpson. (Hmm...so maybe "dumpy" isn't that tough a sell after all...)