Get Lost is a really obscure comedic point-and-click flash game. It has a couple of ways to win, but the real way to win is insane. If you find it on your own, you are awesome. It has dozens of ways to die, most of which you won't see coming. One of my personal favorites is being shot by a cowboy. The art style is intentionally hideous and disturbing. Give it a try.
http://www.e4.com/game/get-lost/play.e4Which Way Adventure:
This is a really old game, featuring "choose your own adventure" style gameplay. It's not as challenging, but some of the deaths are pretty funny. My favorite deaths are death by Pi and the double game over. Can you find them? Tip: Anything involving the word "Manticore" is lethal.
http://www.atrianglemorning.com/games/flash.phpCurse of the Red Ninja:
A more Get Lost-ish style game. Another set of funny game overs (No manticores though) and an achievement system. If you played Get Lost, you should have an idea as to what to expect. When you find your master, choosing "Slay Him" is a bad idea.
http://www.e4.com/game/curse-of-the-red-ninja/play.e4Steamshovel Harry:
Getting away from the silly point and click style of game, he created a neat space platformer game. You play as Steamshovel Harry, a robot with a jetpack. You hop from asteroid to asteroid shooting enemies, taking over enemy bases and all that stuff. It has a really neat plotline involved, and some catchy music. Tip: In area four, do not attack Mirso the instant you spot him. You won't survive the battle. Instead follow him inside the base and attack him in the command room.
http://www.e4.com/game/steamshovel-harry/play.e4