Dungeon Crawling Fools is the first collection of The Order of the Stick (OotS) webcomic and contains strips #1-120, plus 18 new comics and author commentaries.
OotS has become an epic tale and is the most consistently excellent webcomic there is. It features a group of adventures in a Dungeons and Dragons setting. Literally – these are the adventures of D&D characters who are self aware, and a lot of the comedy in this first volume revolves around the author’s skillful blending of game mechanics into his characters’ dialog and actions. The fourth wall is optional when it comes to the good of the comedy here, and in this case it’s a great choice.
Familiarity with D&D will add depth, and no doubt make some of the jokes funnier, but is not necessary to read and enjoy. D&D parody humor and stand alone jokes are particularly prevalent in this volume as Burlew starts to decide what direction to take with his comic, but grows more organically out of the characters and situations in later volumes. Even by the end of Dungeon Crawling Fools, the plot starts to coalesce and several twists and key confrontations have occurred.
OotS’s art uses “fleshed out” stick figures. See the cover for an example. This “simplified” art style is used to great effect and fits the comic perfectly.
I highly recommend Order of the Stick in general, and the beginning, of course, is the best place to start. Dungeon Crawling Fools itself is highly amusing and comprises a complete story arc, but still plants the seeds of future adventures.