Homestar Runner
Flash cartoon comedy site run by two brothers from Georgia, entirely without advertising, which in the early 2000s was one of the most quoted places on the web.
Mike and Matt Chapman built a world of characters around the title figure, but what made the site was Strong Bad Email: a supporting character in boxing gloves who each week read a real email from a visitor and answered in character while typing on a keyboard. More than two hundred episodes came out of it. One of them, in which he was asked to draw a dragon, produced Trogdor — a figure that got its own game, its own T-shirts and a life well beyond the site. The whole operation was funded by merchandise sales, making it an unusual example of a popular site with no advertising. The brothers went on hiatus in 2010 and return sporadically.