Checkerboard Nightmare (available at nightlightpress.com) is a mildly surreal humor comic written and drawn by Kristofer Straub and consistently presented three times a week (Mondays, Wednesdays and Fridays).
Straub plays with meta-humor, poking fun at his main character's attempts at trying to create and popularize a web comic. But he also regularly nails other webcomics (and their own attempts at success), webcomic styles and clichés, webcomic readers, and the occasional faddish webcomic trend. Other issues like ethics, the law, and end user agreements manage to slide in on occasion as well.
The art is simple, clean, and somewhat simplistic, so it’s a bit surprising how well Straub’s characters present emotion. The color scheme is black and white, although Straub does well with color – here’s a good example from 1/8/2001. The background is normally blank, except for special occasions and one very funny self-referential joke from 5/2/2001.
Archives go back to a one-panel version of the strip (format chosen by the UCLA student newspaper) starting in October 1999 and running through April 2000. The four-panel web-based format was introduced in December 2000. Although the creator feels the strip really began January 2001, the older strips have their moments as well.
To borrow a line from one of the creator's own strips, Checkerboard Nightmare is "humorously self-aware" and worth checking out, especially if (1) you like self-referential humor and (2) you know a little about webcomics already (so I wouldn’t recommend this as your first webcomic).