#5 The Undertaker (Age - 26)
Although The Undertaker in the 1990s was nowhere near the performer he would become later on, the Demon of Death Valley would kick off his WWF career in a huge way at the 1990 Survivor Series.
One year after his huge debut as part of the Million Dollar Dream Team, the Deadman would capture the WWF Title at Survivor Series 1991, doing what few men had done before him, defeat Hulk Hogan.
Though this win is historic, it did not come clean, as The Phenom would receive a major assist through a steel chair-wielding Ric Flair. Though Undertaker's reign would come to an end a few days later, the win remains in the history books, as the young Superstar was just 26 years old when he crushed The Hulkster.
This would be the first of several World Championship reigns that the Demon of Death Valley would have during his legendary career, and though many fans are now hoping that the Undertaker doesn't return to the ring after his poor performance at the recent Super Showdown event, it's hard to take away any accomplishments from Taker.