5. Christian
http://www.youtube.com/watch?v=MwZQav4gE8s Before Christian was Captain Charisma and before he had his millions of peeps around the world, he was playing a goth character in 1998. Christian debuted at ringside a few weeks earlier, distracting Edge during his match with Owen Hart, but this was his actual in-ring debut. Taka Michinoku was the WWF Light Heavyweight champion at this point, having beaten Brian Christopher in the finals of a tournament. Christian, with Gangrel as his vampire manager, had the announcers speculating all night as to why he disliked Edge and what the relationship was between the two of them. In any event, Christian countered Taka's finishing move, the Michinoku Driver, and cradled the champion for the pinfall, earning a big reaction from the capacity crowd. Obviously, Christian's character would undergo drastic changes in the next few years but winning the Light Heavyweight title his first match out was definitely a stepping stone on his way to a fantastic career.