The Order of the Stick is one of the most hilarious comics I've ever read. This is impressive, considering that all the characters are stick figures and it is a webcomic. The guy who wrote this wasn't even getting paid to do it at first. But it just goes to show that passion in doing something that you love can pay off in the end.
In The Order of the Stick, we follow a band of six merry adventurers: Roy Greenhilt, the capable yet irritable leader; Haley, the treasure-obsessed and giggly rogue; Vaarsuvius, the insufferable wizard of ambiguous gender; Elan, the goofily crazy and overly dramatic bard; Durkon, the no-nonsense and incredibly-scared-of-trees dwarf; and Belkar, the psychotic and bloodthirsty halfling who may or not be a closet murderer. Through misadventure after misadventure, we follow them as they travel through dungeons and across worlds, hilariously failing as often as they succeed.
Tongue in Cheek D&D
A big part of what makes The Order of the Stick so great is how it goes out of its way to make fun of Dungeons & Dragons and the fantasy genre in general. For those not in the know, Dungeons & Dragons is that game where acne-favored boys and chunky half-walrus half-humans squirrel themselves away from society in order to create characters such as elves and dwarves, sending them on adventures where they roll oodles of strange looking dice and pretend they are people they aren't. Or at least, that is the common negative portrayal of it.
In truth, Dungeons & Dragons is a surprisingly complex game where you use paper, pen, and dice to create and adventure within fictional worlds. Consequently, it is a game that tries to establish an insane amount of rules in order to allow you to do anything that you could do in the real world, along with things that you normally couldn't (use magic, leap tall buildings with a single bound, etc.). Due to the inability to think of everything and due to the fact that the rules do not always make logical sense, it is a subject that lends itself to a great deal of unintentional hilarity, particularly when you try to break the rules.
This is a big part of what makes The Order of the Stick immensely enjoyable. It is a long, ongoing story of a band of adventurers who, while they quest and kill monsters as you would expect, do it with near full knowledge of the ridiculous world in which they live in. They poke fun at the rules that govern their setting, and you get to see the more ridiculous facets of Dungeons & Dragons, along with silly tongue in cheek references to how people play the game.
Subverting the Expected
But, even if you don't have much understanding or knowledge of Dungeons & Dragons, this is still a very enjoyable comic (and you can view it online for freeeee!). The Order of the Stick goes out of its way to take what you expect in the fantasy genre (and in storytelling in general) and twist it in order to surprise you. You would expect the arch-villain to have some megalomaniacal plan to conquer the world, but instead he causes death and destruction simply because he's bored and he finds it hilarious. You would expect the halfling of the group to be jolly and down-to-earth like Bilbo Baggins of Lord of the Rings, but instead he gleefully pranks his fellow adventurers and threatens to kill, well, pretty much everyone. You would expect the attractive, live-life-to-the-fullest rogue to fall for the leader of the group, but instead she falls for... well you'll just have to read and find out!
Consequently, even with all the comedy and humor going on, The Order of the Stick makes for a really interesting story with astonishing depth that never fails to surprise.
In short, The Order of the Stick is very much worth reading if you feel you can appreciate humor based on making fun of fantasy, D&D, and life in general. The only caveat would be that, if you have zero knowledge of or appreciation of fantasy or D&D, 75% of the humor and gags will go right over your head.
The other downside is that the humor is very D&D centric and doesn't really establish much of an overarching story for the first 50 comics or so (out of 700+). It is after this initial hump that it really starts to take off. That is not to say that the first 50 comics of it are bad, but more to say that it gets into much higher quality and depth as you go along.
As for the stick figures, they prove to be astonishingly expressive and, while causing initial skepticism, I wouldn't have them any other way.