Two books for your perusal: The Gallery of Regrettable Food and Gastroanomalies by James Lileks, author of the blog known as The Bleat as well as buzz.mn, the latter part of his duties as a columnist for the Minneapolis Star Tribune.
Lileks is also a dedicated chronicler of pop culture: old radio shows, 20th century advertising and architecture, typography (rock on, James), and the monstrosities of old cookbooks and magazines from the less glorious periods of American cooking. If you'd like to see some of these photos and recipes, check out the website that started it all.
The books are hilarious but best enjoyed in small doses--there's only so much overcooked meat, gelatinous molds, and nauseating combinations of pickled vegetables one can taken in one sitting. I can honestly say that even with my own trend towards the weird and obscure, I haven't had the desire to try any of these recipes. Just look at hot dogs placed vertically in pork 'n' beans.