The Perry Bible Fellowship
The Perry Bible Fellowship started in the Syracuse University newspaper The Daily Orange, and has since become a cult-favorite webcomic. The strips are full of weird, morbid humor, brilliant satire, and has appeared in such highly regarded papers as the UK Guardian. Some have compared it to Gary Larson's The Far Side, and the strip has won various comic awards over the years. Excellent stuff.
Probably the single best-known video game comic on the Web (and there are lots of them), Penny Arcade addresses everything from overly enthusiastic fanboys to the gameplay balance issues in, say, the Killzone 2 demo. Zombies, a talking DIVX player, and a certain robotic juicer all make regular appearances. In addition to the comic, Penny Arcade also hosts Child's Play, a great children's charity, and an annual gaming convention called PAX, held each year in the Seattle area. The Penny Arcade crew even managed to put together its own downloadable Xbox Live Arcade title, Penny Arcade Adventures: On the Rain-Slick Precipice of Darkness.
Get Your War On
One of the best webcomics of all time, David Rees' cult classic is mostly about political issues, and very much the so-called "War on Terrorism." The strip is assembled from simple clip art pictures of office workers that continuously recur (often in the same strip), but this is part of the comic's charm, and fits its disenchanted, cynical take on modern politics and culture. There's now a book out, as well as a series of animated cartoons having hit the Web in 2008 as well.
Achewood is about a group of anthropomorphic stuffed toys, robots, and pets, most of whom live together in the home of their owner, Chris. The absurdist humor isn't about setups and punchlines, but rather hinges quite a bit on non-sequiters and ridiculous, branching weirdness. Fans of Cartoon Network's Adult Swim will find a lot to love here.
Another comic full of biting political commentary, Captain RibMan concens the eponomyous superhero; while he can fly, however, RibMan he spends most of his time reclining in front of the television set and yapping (his cape is actually a checkered tablecloth). He plays off of Billy, the comic's straight man (or boy, in this case), who believes everything he's told. Expect guest appearances by celebrities ranging from Sammy Sosa to Jerry Seinfeld. Though no longer being published, this comic can be found all over the Web in various shapes and forms.
Brad Neely is a weird guy, and Creased Comics shows you exactly how and why. "Cox & Combes' Washington" is perhaps his most popular webcomic, but all of his Web work, including the excellent Professor Brothers is available on Creased. Neely has consulted on South Park and worked on content for Adult Swim and Super Deluxe, and it shows: this stuff is waaay left field, and probably not too kid-friendly (though this depends on your kids, we'd imagine). Be sure to check out his (unauthorized) spoof of Harry Potter called Wizard People, Dear Readers.
Evil Inc, now available both in newspaper and webcomic form, is a hilarious narrative about the trials and tribulations of a business run by supervillains. The comic follows a strong story arc (it's worth starting from the beginning), and parodies plenty of superhero lore and clichés along the way (including Justice League, superfans). Expect lots of puns, parodies, and enough spandex to clothe the Tour de France.
Flintlocke's Guide to Azeroth
This comic is rendered entirely with in-engine stills from World of Warcraft -- and remarkably, it looks great. The characters all self-aware (that is, they know that they're players in an MMORPG), and herein lies the comedy. The strips are mostly about the game itself, full of in-jokes and subtle references; if you've never played WoW (or been a desperate junkie, for that matter), much of it may go over your head. If you're a regular player and haven't checked out the Guide to Azeroth, however, you're totally missing out.
The Adventures of Dr. McNinja
This webcomic is published an impressive three times a week, and concerns the adventures of a character named Dr. McNinja -- who, perhaps unsurprisingly, is a thirty-five-year-old ninja who also happens to be a doctor. The doctor is usually seen wearing slacks, a button-down shirt and tie, a lab coat, a ninja mask, and a stethoscope around his neck, essentially making him one of the best dudes out there. The first story was published in 2004 as a one-off, and the comic has been in regular publication since late 2005.