There’s quite a few of those intentionally poorly designed games, the most infamous of which is I Wanna Be the Guy. My problem (besides the fact that the joke is gone and it needs to rest a few years again before it comes back) is that many of them include bad design in ways that the creator didn’t realize.
Kobolds Ate My Baby
http://www.koboldsatemybaby.com/
All hail King Torg!
The one game that one time in college that entailed drinking a rotating assortment of rotgut beer out of a mixing bowl through a straw. You had to sit in the chair backward and nod your way out of the chute and keep your off hand aloft like a bullrider while you drank and your friends refilled the bowl and counted out eight seconds at the top of their lungs.
There were no winners.
“Bert and Nord Could Not Make Head or Tail of It” by Infocom.
An excellent choice that slipped my mind. A text adventure based on puns and wordplay definitely qualifies as weird.
No doubt more revisionist nonsense from the new editor in chief trying to turn his grandfathers valiant loss into some sort of weaselly victory. If the IMCSC doesn’t get back to focusing on reporting and sober commentary and away from being someones personal sounding board, I may well have to cancel my subscription.
Killer7 would definitely be my vote. It’s also interesting in that the initial weirdness doesn’t quite wear off. There’s the first intial shock. The third stage is probably the weirdest in the whole game. Then you fight some Power Rangers… the final boss is a huge fat guy who’s just been hung on a school auditorium stage… and… yeah… everytime you think you’re getting used to the weirdness quotient of that game, it just spikes up to another level.
I’m going to have to go with Bad Mojo, a 1996 computer game where you took the role of a cockroach.
Well, more specifically, a man who has been magically transformed into a cockroach.
1000 Blank White Cards. We’ve been keeping an ongoing deck for years now, and some of the cards in it are pretty old by now. We use the house rules that at the end of the game, each person gets to pick 5, and only 5, cards to save, and the rest get shredded. Or burned in a fire, when fire is available.
My personal favorite featured a pencil drawing of a coffee cup. It was titled, “Get Me Some Coffee.” At the bottom it said, “I’m not kidding. +10 points. +5 bonus if you get back in less than 60 seconds.”
Ooh, I just remembered: Bureau 13, a point and click adventure game where you can play as several different characters. Among them were a witch, a vampire, a priest, a thief, and many others I can’t remember. Each puzzle had several ways of solving it depending on the characters were using. If I recall correctly, you controlled two characters throughout the game.
It’s really weird, though. For such an enjoyable game, there is precious little information about it online, other than it was apparently based on a pen and paper RPG. I seem to recall that at one point it was released for free, because I obtained the full version with one of those gaming magazines that used to come with a CD full of demos.
EDIT: And put my vote in for Sanitarium. I still have that around here somewhere. I should play it again sometime.
Now excuse me while I go mourn the death of point and click adventure gaming.
It was an interesting concept but as I recall only a few of the characters really had alternative solutions and the vampire in particular just bypassed puzzled.
As I recall the game had been stuck in development hell for a number of years before it was finally released…
The aforementioned Katamari Damacy, although I’ve only actually played the sequel, We Love Katamari.
Space Channel 5 - watch it in action! Aliens have invaded and are forcing people to dance. Enter your character Ulala, a reporter for Space Channel 5 who has to defeat the aliens and free the hostages by dancing, all the while making sure ratings don’t drop on her TV show.
Seaman - dodgy title, weird game where you raise a fish with a man’s head and speak to it through a mic controller. Interesting conversation with Seaman here. Narration by Leonard Nimoy.
It hardly shows the revitalization of the genre or anything, but there’s the Sam & Max game that was released in the last year or two. I have it for the Wii. Talk about a weird game! 
Agreed.
My vote for weirdest game: “The Bright in the Screen”. It’s a flash game from NewGrounds. You play a stick-figure in some kind of 2-D maze. There are other people in the maze who are red stick figures, and touching them hurts you. Some of them don’t move until you get close, some run at you on all fours. You are sent messages by someone/-thing who gives you advice, taunts you, seems to know more about what’s going on, but is also lying to you. It says it can get you out of where you are if you do exactly what it says. One of the first messages is “You can trust me. I’m a good person.” All the while, rather disturbing music plays. You get no information on who you are or why you’re there. It’s all rather creepy, but really fun.