#3 'Cowboy' Bob Orton interfered in The Undertaker and Randy Orton's WWE WrestleMania 21 match
Randy Orton has faced multiple legends throughout his WWE career. Even to this day, WrestleMania 21 marks a special moment for The Viper as a WWE Superstar.
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Randy Orton got to step up against The Undertaker at The Grandest Stage Of Them All back in 2005. The two delivered several promos before the biggest WWE pay-per-view of the year to hype up their feud. 'Cowboy' Bob Orton got involved in this storyline before the aforementioned WrestleMania clash, begging The Undertaker to have mercy on his son.
Bob Orton would later become a huge part of their storyline, and he also tried to push Randy Orton and The Undertaker's WrestleMania 21 match in his son's favor. The Viper gained control of the bout when his father interfered and attacked The Deadman with his arm cast.
The 'Legend vs. Legend Killer' showcase ended with The Undertaker successfully pinning Randy Orton to maintain his WrestleMania streak at 13-0, back in 2005. The Apex Predator's long-term feud with The Phenom later went down as one of the most exciting feuds in WWE history.