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#4 "Cowboy" Bob and Randy Orton
Randy Orton is regarded as one of the best Superstars of his generation and is currently a major heel in WWE as of this writing. In 2005, Randy's father "Cowboy' Bob Orton was inducted into the WWE Hall of Fame. At the same time, Randy was busy establishing his moniker as 'The Legend Killer' (a gimmick which he has recently brought back again) in WWE by attacking and taking out legends.
Randy Orton then set his sights on The Undertaker with the hopes of breaking his Streak. The elder Orton aligned with his son in the bitter rivalry against The Deadman when he unsuccessfully interfered in Randy's match against Taker at WrestleMania 21.
Later that year, a rematch for the two Superstars was made at SummerSlam and this time around, the WWE Hall of Famer was able to help his son defeat The Undertaker. This led to both the Ortons drawing the fury of The Phenom and at WWE No Mercy 2005, the father-son duo took on The Undertaker in a Handicap Casket match and defeated him.
