Most of Weird Al's Album covers. Highlights include: "Off the Deep End", parodying Nirvana's "Nevermind", "Alapalooza", which parodied the Jurassic Park movie poster, and "Even Worse" which parodied Michael Jackson's "Bad".
Crap, you beat me to it. You could put most of Weird Al's album covers in this thread. His most recent album, Alpocalypse, features Al, in his Hawaiian shirt and sneakers, cheerfully waving while riding on the back of a demonic horse in a hellish scene along with the other horsemen of the apocalypse
Ah yuck! It's gross because for a split second you're like "hey!" until you realize THEY ARE DUDES! It's like looking at Rupaul and getting momentarily tricked. You feel swindled. lol.
The back of that one also has the other members of his band laying on the track with various scissor related injuries.
Let's face it, Weird Al is a master funny musician. Side note: He also directs a lot of music videos. Like, for regular artists, not just his own stuff.
I have a signed copy of AlPocalypse, the Amish Paradise single, and Peter and the Wolf. On topic, there are a number of hilariously bad album covers from church groups. Consider... Or... And even...