#3 HBK infamously posed for Playgirl Magazine
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Back in 1996, before it became popular for the women of WWE to pose for Playboy magazine, Shawn Michaels thought it would be a good idea to pose nude for Playgirl magazine.
A now infamous image from the photoshoot includes HBK posing with the WWE Championship covering his private parts, a photo which drew HBK a lot of flack from the boys in the WWE locker room.
The decision to pose for Playgirl was controversial in that it mostly backfired for HBK, and led to a transformation of HBK's character which saw him behave more like a "stripper" in the ring, complete with a new, riskier wardrobe and flashy moves during HBK's ring entrance.
Michaels deciding to pose for the magazine paved the way for his 'sexy boy' gimmick and routine, which followed on the heels of HBK's rise to the top in WWE that came along with a bolder, more controversial backstage version of Shawn Michaels.