Wow, Bow. In May 2010, MediaTakeout reported the existence of a homemade Adult Videos video that involved some dude on dude action and said that one of the dudes was a popular rapper. They posted a still frame from the alleged flick and one of the cats in the video had a striking resemblance to Bow Wow. Of course, the full video never surfaced, and the Cash Money rapper denied it was him in the picture taking it in the dookie chute.
Dishonorable mention: Benzino, Prodigy