1. Big Bear, Doin' Thangs

Year: 1998
Label: Tru Game

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This cover is so bad that it's great. We couldn't not put it on this list. Everything about this is epic: from the dripping-honey and terrible "Doin' Thangs" font choices, to the pimp robes, and do we need to mention the bears?! We are so conflicted about our hatred (love) of this cover.