So Bad It's Good/Tabletop Games

At least for some readers, Gary Gygax's prose style is reminiscent of the Mencken quote atop this page.
The Dungeons & Dragons Character Name Generator has a tendency to produce unintentionally hilarious names.
To many, World of Synnibarr qualifies. While the mechanics are terrible and the setting incoherent, it's still a game with a "midnight sunstone bazooka", mechanics that affect the next character you roll up, and an actual Deus Ex Machina roll to see if your patron deity turns up to save your life.
Strike Legion is what Limbo of the Lost wants to be: Something that ripped off so many sources it digs right out of the barrel-bottom of absolute shit and becomes hilarious awesome. Have a MST and mind the picture load.
In Magic: The Gathering, some cards that are bad in terms of gameplay and power level may become loved and appreciated for their goofiness and quirkiness. Examples are Chimney Imp and Storm Crow, which have both become memes in the Magic world.
- Storm Crow is only a Common Knowledge example. The card itself is not and has never been bad. It isn't a great card and most blue decks don't need it, but that isn't the same thing as it being bad.