Nice entries everyone! It was really hard to narrow them down to even five!
Some of these are absolutely amazing photoshops, but with confusing, dull, or poorly executed concepts. Others are some of the funniest ideas when you think about it, but a horrible, horrible photoshop. No excuses you MSPaint punks!
Ultimately, I chose 5 that I thought both fit the "point" of the contest in a clever way, and in a way that I can tell some effort was put into the photoshop.