Kris Straub is one of the nicest guys I've met in webcomics (although 99% of that was before my brief saying "hi, 'sup" at last year's SPX).  Besides being part of the ever-present Half Pixel crew (with whom he wrote How To Make Webcomics) and working on lots of comics and animated series (say, when is PvP Season 2 coming?) he's got a new album out called Aviators Hide the Tears that includes that rollickin' "I'm on the Internet..." song he wrote (I can't remember the name of it but it runs on his slipcast videos).

Also he does make a lot of comics.  His main gig these days is the science-fiction flavored Starslip Crisis which to my mind is one of the smarter comics out there.  Kris' strength and weakness in writing is often going meta on things -- making the joke and simultaneously analyzing it.  To my mind it works more often than not and really with Starslip he's broadened his approach to everything so that "meta-ish" isn't so predominant in his work anymore.

If you want a concentrated does of meta, however, check out Straub's re-run of his first comic, Checkerboard Nightmare, where he basically made a comic about webcomics and online culture, circa 2000ish.  For the re-run he's making short video commentaries.  We ran two Straub comics at ComixTalk -- Modern Humor Authority and later installments of Checkerboard Nightmare -- both some of my favorite things we've published.