Fail Occurred: 5/22/2009

Charles Hamilton had only just begun his fall from grace when he and his manager Briana Latrise were spotted walking down an L.A. street. In the middle of a playful on-camera freestyle battle, Charles insults her, revealing that she'd had an abortion by him. Briana tries to shove his words back into his mouth—literally—with her fist. The bruise may be gone, but he may never recover. Things only got worse when this this GIF hit the Internet.