What better way to kick off this series than by featuring a webcomic about webcomics? Kristofer Straub's CHECKERBOARD NIGHTMARE lays it all out in the very first strip (which doubles as a cast page): Chex is a cartoon character obsessed with webcomics. He wants to go all the way to the top without investing any long-term effort or talent. Since this shake-and-bake strategy brought about the Great Boy Band Epidemic of the early '00s, it's hard to argue with his logic. Unfortunately for Chex, all he's got going for him is a short attention span and a knack for plagarism. Fortunately for us, that translates into a brilliant comedy that follows our hero's hilarious schemes.
CHECKERBOARD NIGHTMARE has a lot going for it: it's based on a simple four-panel formula where the first three panels set up the punchline and the fourth panel delivers, and this runs on a daily basis for five years, but even Straub's most repetitive gags (ie: Vaporware's choking fetish) never cross that line where they stop being funny. His style of humor is sophisticated without being exclusive, and that's important to me as a reader because I don't see the funny in fart/poop jokes, but the other end of the spectrum can come off as horribly pretentious.
I think the key to Straub's success, the reason why CHECKERBOARD NIGHTMARE is so entertaining, is his understanding of the principles of balance: just when you think you're getting tired of the done-in-one jokes, a whole storyline pops up about Chex's #1 Fan (there is no #2 Fan), or a send-up of cop-based action series, or a glimpse of Dot's ill-fated singing career. And not to spoil the ending, but let's just say Straub makes an astonishing use of continuity during the series' climax.
This strip is also unique in that, while it heaps satire on specific webcomics as well as the conventions of the medium itself, it's also a fairly educational tool. It's part of the strip's duality, a rather clever trick Straub is playing: every strategy or gimmick Chex fails to appropriate has succeeded elsewhere, whether it's using insult humor (SOMETHING POSITIVE), joining a popular webcomic group (Keenspot, Graphic Smash, etc.) or using a "safe format" to attract wider demographics (GARFIELD). These tactics don't work for Chex, largely because he misunderstands why they're supposed to work (and that, in turn, goes to the core of the character's comedic tendencies), but they're the foundations of many other popular series.
So in reading this EXCELLENT series, not only do you come away with a smile, you might actually learn a few things about webcomics too.
A few technical notes to wrap things up: the main CHECKERBOARD NIGHTMARE series ran from November 10, 2000 to November 11, 2005. Though Straub released a few sporadic strips after the big wrap-up, they were mostly topical done-in-one gags. According to the FAQ, the series has no regular update schedule - prior to its most recent August 31 update, the series was last updated September 1, 2006. Straub has since moved on to STARSLIP CRISIS, another EXCELLENT webcomic I'll probably be reviewing at a later date. The archive is conveniently ordered both chronologically and by storyline, making for easy navigation. The strip is primarily in black-and-white, though Straub switched to color during its final year.