Ctrl Alt Del - Tragically l337:: A favorite webcomic. Centered around obsessive gamers. So funny. Even though I'm quite thoroughly out of the videogaming loop, all the references to various games are still hilarious, and the interactions of the characters are dear. And there's a penguin.
Questionable Content:: I love this webcomic.. 'wonder how I didn't know of it sooner. Music, people, anthropc.
Striptease:: A webcomic strip about characters who write comics.
Red Vs Blue:: Video spoofs of the game Halo, these care hilarious even if you've never played the game. At least read their FAQ.. and aspire to watch their Lopez episode.