Paste receives a lot of CDs. And by a lot, I mean a lot. Everyday the interns haul in crates of manilla envelopes from the mid-morning post office run and get to work labeling and filing each album. This means, for better or for worse, we interns see most of what comes through these doors. And let me tell you, some of it is not pretty (aesthetically speaking). Here are my picks for the most cringeworthy album covers I've discovered in the depths of Paste's cache of CDs thus far.
(Note: This has nothing to do with the music on the albums, most of which, admittedly, I have not listened to. Qualifiers were judged solely on first impressions. Some are included for their sheer gore, others simply for their lack of, uh, elegance.)

David Karsten Daniels, Sharp Teeth: Call me crazy, but there's just something about cannibalism that rubs me the wrong way.

John Nemeth, Love Me Tonight: Classy has never looked so un-classy.

David Gans, The Ones That Look The Weirdest Taste The Best: Serenading an onion. It just had to be included.
Placebo, Meds: Just plain creepy.
Isaac Hayes, Juicy Fruit (Disco Freak): This one is actually kind of awesome, but his facial expression was just too much. It had to be included.

Ralph Covert & The Bad Examples: Good Examples of Bad Examples: Okay, so maybe it's not fair to include "children friendly" album art. But c'mon, it looks like a child could've made this cover.

Geoff Berner, Klezmer Mongrels: This one is bearable, but still slightly off-putting. Oddly enough, I think it's the tails that bother me more than the breasts.

Darunam/Milan, The Last Angel On Earth: The glistening, ripped-out heart. It's just so fleshy.

hilarious!
Actually, I think he's serenading something more like a radish or possibly a rutabaga.
It's a turnip. A worried turnip.
P.S. Does this mean no one is going to actually listen to it and/or review it?
For those reading this- Do yourself a favor and take a listen to David's CD (or go see him live) if you have not already...the album is full of great folk-rock music, arrangements and lyrics that reflect some major themes from today's society.
http://www.dgans.com/weirdest/