With over 1000 strips, Rich Burlew’s The Order of the Stick is perhaps one of the most prolific webcomics of its kind.
The Order of the Stick follows a group of (mis)adventurers in a Dungeons and Dragons-inspired setting. Drawn as stylized stick-figures, the diverse cast of characters blend archetype and stereotype about fantasy and gaming (fourth wall gags abound).
I will allow my conciseness to speak for just how much I love this comic. Please, go read it!
P.S. The writer, Rich Burlew, held a Kickstarter campaign many years ago in order to republish at least one of the print runs of the comic (which are also fantastic as they include bonus material). Secretly, he intended the campaign to be a litmus test: if the Kickstarter failed, he was going to abandon the decade-long project. To his surprise, the readers came out in full force; the Kickstarter proved to be one of the most successful artistic campaign of that time, being the third Kickstarter to break the $1 million mark.
As I said, go read it!