10 Ways To Successfully Challenge The Undertaker At WrestleMania

5. Be A Legend Killer (Randy Orton - WrestleMania 21)

On the opposite end of the spectrum from King Kong Bundy, Randy Orton's best years were still ahead of him when he faced The Undertaker at WrestleMania 21 in 2005. Known as the 'Legend Killer', Orton had earlier challenged the likes of Shawn Michaels, Mick Foley and disrespected a host of other icons in the history of wrestling, such as the legendary Harley Race. The gimmick seemed tailor-made for Randy, who was able to break out of the shadow of his former members in Evolution, Triple H, Ric Flair and Batista, carving his own path in WWE with the upstart character. It was only inevitable that Orton would collide with the promotion's resident legend, The Undertaker, and seeds were sown for the feud by 'Superstar' Billy Graham, who assured Orton defeating The Phenom was the only way to secure his own place in the history books. Up until this point, The Undertaker wasn't known for routinely having the best in-ring offering at WrestleMania, but his match with Randy Orton was a standout on the card, which is no mean feat considering this was the year the Money In The Bank Ladder Match debuted.