This piece was one of the first published by the artist and game designer Tom Wham, who joined TSR is 1977. It first appeared in the 6th printing of the original 'White Box' edition of Dungeons & Dragons, replacing the section of text that in previous printings had described the Balrog--excised due to legal pressure from the Tolkien estate. It also appeared on the front page of the 1979 bluish 'wizard logo' Character Record Sheets.
Here they all are--the Fighter with his sentient magic sword, the conical-capped Magic-User hiding behind him, the Thief in the process of picking the Magic-User's pocket and the beneficent Cleric (is he trying to gently dissuade the Thief or naively oblivious to his action?). To me, they are united in having an almost maniacal look about them, as if to say, this is what the lure of treasure does to everyone.
Wham would do many other drawings for TSR and later other companies including his own, often combined with game design such as in his brilliant Awful Green Things from Outer Space. Most of his drawings were comical or light-hearted in style but not all of them. He also composed the Monster Manual's Beholder. (Though, now that I look at it again, even that awful creature appears ever so slightly comic.)
In a blog post contrasting his work with that of David Trampier, Matt Finch references the above drawing while aptly describing Wham's contribution:
...Tom Wham's picture is an adventuring party seen from the outside, from the perspective of the gamer looking in. Because let's face it, most of our gaming sessions have plenty of Tom-Wham-adventurer moments in them. Quoting Monty Python? That's the Tom Wham guys. Dancing around the table when your roll for dexterity comes up triple 6's? That's the Tom Wham guys.
Quick quiz: In what fundamental ways does 2nd edition Advanced Dungeons & Dragons differ from 1st edition? THACO and skills would be possible correct answers, of course. But here's another one:
There are no cartoons in 2nd edition AD&D.
Or at least there aren't in the 2nd edition Dungeon Master's Guide. Contrast this with the multiple cartoons (with captions!) liberally sprinkled throughout the original DMG:
So here's another difference between the old school and newer editions (for those of you still keeping count). The old school had a sense of humor. Newer editions often give off a ponderous air of humorless self-importance, as if to say, 'don't laugh, it will break the spell'.*
Also, prestige classes aren't funny.**
Recently Jon Peterson unearthed and published a sort of variant or possibly even proto-version of Dungeons & Dragons, played in Minneapolis in 1974. Among other things it featured giant carnivorous meatballs. I think many of us would agree that 'official' OD&D was wise not to go that far, though if you wanted more of that sort of thing, there was always Tunnels & Trolls.
However, in the Golden Age of the game, there was a sense (at least at some level) that things shouldn't be taken that seriously, partly because we all were well familiar with how the game was actually played. Despite some of the fantastical depictions in the media--like Tom Hanks and friends sitting around a spooky table that featured candles and crystals--we all knew that in the end we are all just a bunch of pimply kids getting potato chip grease on our graph paper and riffing about Monty Python or Doctor Who in between rolls.
The game was cool. No question about it. But what was wrong with laughing with it and at it from time to time, as well as (on occasion at least) laughing at ourselves?
*2e was still old school in many ways, and to be fair, I liked much of the art in 2e, but on some things the vibe had already changed.
**Unless you say some of the names aloud to your wife. For the list of over 800 prestige classes I published a few weeks back (stolen from Wikipedia), I stuck a few phony names into it--such as inserting 'Swiss Burger with Bacon' in between 'Swift Wing' and 'Sword Dancer'--to see whether anyone was paying attention. My wife, at least, thinks I'm a funny man.
'Wearer of Purple.'
'That's hilarious. You're a funny man.'
'I didn't make that up. It's one of the real ones.'
'You're lying. You made that one up.'