#1 The Rock (Age - 26)
The Rock won his first WWE Championship at the Survivor Series Pay-Per-View event in 1998 after defeating Mankind in the Deadly Games Tournament. In a repeat of the Montreal Screwjob the year before, Vince McMahon turned on Mankind to assist the 26-year-old in winning the championship.
Little did anyone know that this shocking heel turn would give birth to arguably the most charismatic star of the Attitude Era and one of the most charismatic stars ever. He would win the belt a few more times before turning 30, and still had plenty of accolades outside of the top prize.
Before turning 30 in 2002, The Rock featured in the main event of WrestleMania 15, 16 and 17, and also fought in the biggest match of the night at WrestleMania 18, where he defeated Hulk Hogan.