#7 Ric Flair

Ric Flair's grand entrance for his final WWE match at WrestleMania 24
His Wrestlemania Record: 1-4
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Nature Boy can be forgiven for his paltry number of appearances at the Grandaddy of 'Em All; spending most of his glory years in a rival territory kept Naitch out of the Wrestlemania spotlight for a majority of his career, and after WWE's buyout of World Championship Wrestling, Flair found himself in a managerial role at several spring spectaculars.
Still, though, the man famous for being the most decorated champion in professional wrestling history (at least where world titles are concerned) has won a paltry 20% of his Wrestlemania contests!

Signature Loss: No discussion of Ric Flair Wrestlemania losses is complete without talking about Wrestlemania XXIV in Orlando, FL, where The Nature Boy put his career, and his early 2008 win streak, on the line against "The Heartbreak Kid" Shawn Michaels.
The match was classic Flair, busting out every dirty trick that got him through the 1980s, and some we hadn't seen since Harley Race was Handsome (like the top-rope cross-body); ultimately, HBK had to apologize to Flair, and remind Flair of his love, before a superkick ended Space Mountain's WWE career.
At Least He Won When: Flair's lone Wrestlemania victory comes as part of a team, when Evolution took on The Rock 'N' Sock Connection in a 3-on-2 Handicap Match at Wrestlemania XX; while not a barnburner of Wrestlemania Moments, the match was well-worked and well-received, and Rock's Flair-aping People's Elbow was a sight for the ages.