THE SECRET OF MONKEY ISLAND / LucasArts / PC
In 2009, two decades after its initial release, The Secret of Monkey Island isn't quite as laugh-out-loud funny as it was when it first came out, in a time when it was a shock to see an adventure game parody and deconstruct the conventions of its own genre. That said, it is still definitely good for at least a chuckle.
And it is important that the game be funny, as it is a bit on the short and easy side. Wannabe pirate Guybrush Threepwood comes to Melee Island with nothing but his dreams of becoming a real buccaneer; to this end he'll undertake fetch quests for the Important-Looking Pirates, fall in love with the island's beautiful governor, and eventually go head to head with the undead menace Lechuck. All-in-all this will give you maybe four or five hours of gameplay at most, and while the puzzles are fairly obvious and not diabolical, they are also logical and never head-spinningly abstract. And as with most LucasArts adventures, you can't die (with one Easter Egg exception) or get irrevocably stuck.
Buoying the game is an excellent calypso soundtrack (that unfortunately appears rather infrequently, mostly leaving the game to silence) and really nice hand-drawn VGA graphics.
* The Scumm Bar
* Everything I Know About Anything I Learned From Guybrush Threepwood
* Gameplay Video