#2 Mark Henry

His Wrestlemania Record: 2-9
Mark Henry, another member of the 2018 WWE Hall of Fame Class, has a long WWE career with numerous accomplishments, which is especially impressive considering his less-than-stellar debut following the 1996 Olympic Games. Henry was pushed very heavy, very fast, and spent most of his career sliding up and down the card while appearing at nine consecutive Wrestlemanias throughout the 2000s.
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Most of his Wrestlemania appearances came in the form of battle royals and two Money in the Bank Ladder Matches; while his chances might have been high in the former (as battle royals are a big man's game), few, if any, WWE fans could imagine him winning the latter (by climbing any but the lowest rungs of a ladder).

His Signature Loss: At Wrestlemania 22, Henry added to the ranks of Undertaker's legendary streak in a casket match; while the match was a plodding slugfest for much of its runtime, the ending sequence saw Henry on the receiving end of an eye-popping Undertaker plancha, a Last Ride powerbomb, and a massive Tombstone Piledriver before being stuffed in the oversized coffin.
At Least He Won When: Henry has only one win in a one-on-one singles match at Wrestlemania, and it came at Wrestlemania 29 when Henry fed Ryback more than The Big Guy could handle, reversing a Shell Shock to crush Ryback to the mat for three (although Ryback would finally hit the move after the bell rang).