I made a vote for an ADRIFT game ("The Worst Game in the World... Ever!!!" by David Whyld) on IFDB's latest poll, "Absolute worst IF," not as a bash, but in recognition of an aesthetic goal. What with all the talk of newbie games and mistakes lately, I thought it was kind of a fun coincidence to be able to bring up ol' Clueless Bob.
Pretty sure everyone here has played it, but if you haven't or you're new to the Forum-- check this one out.
I also voted for "The Absolute Worst Game in IF History," by Dean Menezes. Not sure such a game needs to be played to be understood... the treasure in the game is the Scarab of Floccinaucinihilipilification*. Apparently, there is some question as to whether it is actually possible to win it. Seems to be a statement on design against mazes, randomness, and cruelty, but also a meta-commentary on criticism and the writing of "bad games" in general. Indeed, calling something worthless seems to be a treasure for some critics and even some authors, or else one assumes the "intentionally bad game" sub-genre wouldn't exist.
*For those not in the know, "floccinaucinihilipilification" is a real English word (the longest undisputed word in the language!) which means "the estimation of something as worthless."