Career
Career beginnings
In 2002, Wizards of the Coast announced a contest to find a new campaign setting for their D&D game, dubbed the Fantasy Setting Search. From a field of over eleven thousand gamers who sent in one-page descriptions of their worlds, one of Burlew's four entries was chosen as a finalist. He was asked by Wizards of the Coast to produce a one hundred-page setting bible for his world to compete against two other designers. The contest was won by Keith Baker's Eberron setting, with Burlew and P. Nathan Toomey as the other two finalists. Although he did not win the contest, the experience encouraged Burlew to pursue a career in game design. As his entry in the competition remains the unpublished property of Wizards of the Coast, Burlew is prohibited from discussing it by a non-disclosure agreement. However, he was offered additional writing work from Wizards of the Coast the following year in which he contributed monsters such as the "battle titan" and the "shade steel golem" to the Monster Manual III rulebook.
Burlew was able to take advantage of the attention and popularity he got from the Setting Search contest by launching his "Giant in the Playground" website and the comic The Order of the Stick. In June 2003, Burlew launched the website GiantITP.com in hopes of "turning [his] paltry name recognition into something resembling a job." He dubbed his new site, Giant in the Playground, after his screen name on the Wizards.com forums in order to capitalize on his reputation as a knowledgeable gamer.
Webcomics
GiantITP.com languished for several months until Burlew added a webcomic to bring in recurring traffic. He started The Order of the Stick, a stick figure fantasy webcomic, in September 2003 by transferring the images from the stick figure miniatures he had produced for his D&D game into a page-long comic. The Order of the Stick gained popularity through 2004. Burlew realized that he had created a successful story when several friends in an online D&D game spent an entire session berating him for writing a scene in which a villain impales a main character. He announced the publication of the first strip compilation in December 2004. Shortly thereafter, he reported that pre-orders for the book had been so successful that he was prepared to quit his job as a graphic designer and commit himself full-time to comic and game writing. Since then, he has produced five additional compilations and three black-and-white prequels for The Order of the Stick that are not featured on the website.
In November 2005, new strips of The Order of the Stick began appearing in Dragon Magazine, significantly extending the potential reach of the comic. Burlew described the feeling of seeing his work on the same page that once held the comic What's New with Phil & Dixie as "awe-inspiring" and "weird". The comic ran in the magazine until its final print issue. These strips were later published in the compilation book called Snips, Snails and Dragon Tales.
Burlew also drew a short-lived webcomic for the Role-Playing Game Association (RPGA) website, Five Foot Steps, that featured more traditional cartoon art instead of stick figures. These depicted a diverse role-playing game group at the fictional Rollmoore College. The strip only lasted for five installments for reasons that have not been made public.
In January 2012, Burlew launched a Kickstarter campaign to get The Order of the Stick: War and XPs back into print, which eventually raised enough money to reprint the whole book series. The drive was the most funded creative work in Kickstarter up to that point, getting more than twenty times the original goal for a total of $1,254,120. During the reprint drive Burlew committed, as rewards for meeting increasing funding goals, to write eight new short stories either about specific characters or in alternative non-canon settings; the characters for three of these stories were chosen by backers as part of the pledge reward.