Grandson of wrestler Bob Orton and son of "Cowboy" Bob Orton, Randy became a third-generation wrestler in 2000 when he made his wrestling debut for Mid-Missouri Wrestling Association-Southern Illinois Conference Wrestling. He joined WWE's developmental territory in 2001 before being called up to the main roster in April of 2002. Initially seen as a bland babyface, he soon suffered a shoulder injury that led to a character change. During his recovery, he appeared in vignettes where he gave vain and tone-deaf updates on his injury. After his recovery, the cocky new heel joined Triple H's villainous faction Evolution, where he developed his "Legend Killer" gimmick: a young upstart and the future of wrestling, spitting in the face of and defeating legendary wrestlers. Randy had notable feuds with Mick Foley and The Undertaker, before winning the WWE World Title at SummerSlam 2004, becoming the youngest world champion in WWE history.

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