10 Longest Times Between First And Last WWE Title Victories

6. Shane McMahon - 15 February 1999 - 27 January 2019 (19 Years, 11 Months, 12 Days)

Ted DiBiase title
WWE

The near twenty-year gap between Shane McMahon's first championship and his most recent rather highlights how unusual it is that, in spite of this extended tenure within the business, the decidedly middle-aged Boy Wonder still isn't quite considered a 'proper' wrestler.

There are a few reasons for this. For one, the enduring neophyte status is somewhat informed by nepotism, but there's also the fact the chairman's son took a sabbatical from the business entirely for the best part of a decade before his surprise 2016 comeback - which naturally saw him paired with The Undertaker in a de facto WrestleMania main event.

It's this lengthy absence, combined the fact he's virtually guaranteed not just a job but a place at the family's top table, which has allowed Shane to place so highly in this peculiar category, thanks to a SmackDown tag team champion victory two decades after he claimed the European Championship as a fresh-faced silver-spooned sprog.

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Benjamin was born in 1987, and is still not dead. He variously enjoys classical music, old-school adventure games (they're not dead), and walks on the beach (albeit short - asthma, you know). He's currently trying to compile a comprehensive history of video game music, yet denies accusations that he purposefully targets niche audiences. He's often wrong about these things.