Some games obviously aim to have a laugh at their own expense and I appreciate that. Some other games seem to take themselves fairly seriously and any laughs are secondary. Artistic presentation in the game is a good clue indicating what the designers have in mind - whether it's the game's subject matter, or its genre or its attitude toward play. Even a fairly serious game such as chess can be presented in a more humorous light when the chess pieces are sculpted to represent cartoon characters or other "comic" subjects rather than using the traditional style chessmen.
Tabletop roleplaying games run the gamut from the very humorous to the very serious, and many are in between the two extremes. At its heart, the adventure game is about exploration, combat and acquisition. The illustrations that excite our imagination also inform us about the game designer's vision for what the game will offer. (It's also an aspect of marketing, but I have less to say on that topic.)The illustration above is taken from the "advanced" edition and seems both humorous and informative. The dark corridor is the setting for a likely encounter between an adventurer and a hideous monster, both are winding the same string about a stick and this is leading them around a corner and into a surprise situation where they will suddenly be face-to-face. It's a bit dark perhaps, but I find the situation humorous.
The Advanced game is ripe with more serious illustrations suggesting that the game is about "scary" creatures who seriously threaten the lives of the paper warriors and wizards we players control as our in-game alter egos. A quick glance through the Advanced books will reveal the designer's intent is to be both seriously dangerous (to the paper heroes) ...
...and humorous. In this way, the game offers a juxtaposition between dark and dangerous adventuring and an occasional chuckle that is both light-hearted and fun. The Advanced game essentially "pokes a bit of fun at itself".
What is ultimately revealed is that a sense of mystery and discovery is to be had in the game's milieu that is both fantastic and a bit familiar. This is indeed what the Advanced game promises.
We can see that a fantastic setting is suggested by the cover illustration to most all editions of The World's Most Popular Role-Playing Game and something similar also appears on the covers of its many imitators, all leading us, the hobbyist and consumer to conclude a lot of this type of thing will occur during game-play. The artistic style and amount of heroic violence on display in the illustrations varies considerably from product to product, but there is a common theme to most - fantastic creatures, especially dragons, warriors and wizards facing a degree of peril and magical violence, and perhaps the seed of a story to prompt our imagination.
For me personally, I find no better single depiction of what the hobby is about than this full-page interior graphic from the pages of the 1978 Advanced players handbook.In this scene we see a party of delvers, specifically characters who are likely controlled by the players and consist of peoples drawn from familiar fantasy traditions who armed with torches and swords are traversing the dim halls of some ancient and long abandoned (underground?) edifice. As the delvers pass by the massive stone support column either on their way in or out of the place of mystery they have triggered a "magic mouth spell" appearing upon the wall. The message the mouth delivers is perhaps a warning, a clue to wealth or survival, or it even may contain a curse that will give give players pause. Whatever the message, the magic mouth spell gives the referee a means to engage with their players so as to help them bring the setting alive through imagining the in-fiction action, and to deepen the sense of wonder they may be experiencing as part of the fun of the game.
In the nearly half century since its first publication, I have watched as The World's Most Popular Role-Playing Game has evolved from its origins as an amateurish outgrowth of wargaming, through its more mature "advanced" version as seen in the illustrations featured in this post, and beyond - currently into a 5th edition that seems on the cusp of becoming predominantly an experience on a digital game platform that will perhaps include an A.I. "game master". If the artificial gamemaster does come about, will its designers program in a sense of humor for it? I wonder?