1. Ric Flair – 56 Years, 6 Months, And 24 Days
“The Nature Boy” Ric Flair is a 16-time world champion, but he never held the prestigious Intercontinental Championship. Flair challenged Carlito for the title at Unforgiven 2005, seeking to add the Intercontinental Championship to his overflowing trophy cabinet.
Flair cinched in the Figure Four Leglock, leaving Carlito no choice but to submit, and he captured the Intercontinental Championship for the first time. He became one of the oldest titleholders in the Ruthless Aggression era, and the oldest man to win the Intercontinental Championship at 56.
Flair’s Intercontinental Championship reign was Flair’s first singles championship reign in WWE since he held the WWE Championship 13 years prior. Moreover, Naitch became a Triple Crown winner after winning the WWE Championship twice and the World Tag Team Championship twice with Evolution stablemate Batista. Flair’s Intercontinental Championship victory completed the Triple Crown set.
Naitch’s run as Intercontinental Champion was successful, notably including a win over his former Evolution ally Triple H in a steel cage match at Taboo Tuesday 2005. The Nature Boy’s lone Intercontinental Championship reign lasted five months until he dropped the title to Shelton Benjamin on Raw’s February 20, 2006 episode.
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