#1 The Big Show

His Wrestlemania Record: 5-11
While boasting the most wins of anyone on this list (and, really, more wins than the rest of the list combined), Big Show makes this list because of the magnitude of some of his biggest Wrestlemania losses.
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Paul Wight came to WWE in early 1999, one of the first defectors to leave World Championship Wrestling for the World Wrestling Federation just as the scales of the Monday Night Wars were tipping in the McMahon family's favour.
Winning the WCW World Championship in his debut match, and winning the WWF Championship within nine months of his shocking entrance into the Northern territory, Big Show's stock (and karmic alignment on the heel/face scale) has fluctuated over the past nineteen years more than any other superstar.
His career reportedly done, Big Show has competed in sixteen Wrestlemania contests, and come away with a win in fewer than a third of those.

His Signature Loss: The Big Show's Wrestlemania calling card is his willingness to tumble with celebrities from other "legitimate" sports, and his No Disqualification match with Floyd "Money" Mayweather at Wrestlemania XXIV is the most famous example of this (although Show would tussle with Akebono and Shaquille O'Neal at other Mania events). Wight was reportedly up for anything in this match and has spoken at length about asking the pint-sized pugilist to punch him for real both in the buildup to the match and the contest itself.
At Least He Won When: Show's only victories as a singles competitor at WrestleMania XXVIII, when he beat Cody Rhodes for the Intercontinental Championship, and Wrestlemania 31 edition of the Andre the Giant Memorial Battle Royal, ironic considering that WCW once billed him as the son of the late French behemoth.
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