5. The Undertaker
Taker captured his first WWF Championship at Survivor Series 1991. He was just twenty-six at the time and was shy of his twenty-seventh birthday when he won the Championship. To be technical (as there are three men who were twenty-six on this list), Taker was twenty-six years, eight months and three days old.
Taker won the Championship from Hulk Hogan thanks to Ric Flair, but would lose it to Hogan six days later at Tuesday in Texas. WWF President Jack Tunney would vacate the title, as both matches had controversial endings. He would then award the Championship to Flair when he won the 1992 Royal Rumble.
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