The Rapper: Charles Hamilton
The Fail: After taking an L in a rap battle to Serius Jones, CH tracked Serius down at a barbershop in Harlem and attempted to battle him again. But, Serius basically told him, "Go find somebody to put some money up for the battle first," after Charles attempted to engage him and walked away without agreeing to a battle. And yet, for whatever reason, we still thought Charles had a good thing going with his rap career after seeing this. We failed here, too!