In the early 1980s, Orton competed in the World Wrestling Federation. Competing as a heel, he challenged Bob Backlund for the WWF Heavyweight Championship, but was unsuccessful.
Orton re-joined the WWF in 1984 for what would be the most famous run of his career. He was often addressed as "Ace" Orton by Roddy Piper, and was Piper's bodyguard. His other gimmick, wearing a cast during his matches, stemmed from legitimately having his left forearm broken in a match with Jimmy Snuka at the 1985 event The War to Settle the Score in Madison Square Garden. Although the injury healed in real life, the "cast" gimmick involved Orton—on "doctor's orders" -- continuing to wear the cast, claiming the injury had not healed; Orton instead would use the cast to his advantage, striking his opponents behind the referee's back.
Orton was involved in the main event of the very first WrestleMania at Madison Square Garden in 1985, being in the corner of Piper and 'Mr. Wonderful' Paul Orndorff in their match against Hulk Hogan and Mr. T. Orton accidentally cost his team the match after an attempted cheat backfired, resulting in him hitting Orndorff with the cast. Orton also competed in the main event against WWF Champion Hulk Hogan on the premiere episode of Saturday Night's Main Event on NBC broadcast May 11, 1985, which he lost by disqualification due to the interference of Piper.
Orton remained with Piper for the remainder of 1985, feuding with Orndorff and a variety of partners, such as Hogan, André the Giant, and Bruno Sammartino. In early 1986, Orndorff began wearing a cast as a neutralizer and the WWF ordered both men to remove the cast. Also in late 1985 and early 1986, Orton challenged Hogan for the WWF Heavyweight Championship; like his matches four years earlier against Backlund, Orton was not successful.
Orton was dubbed "Boxing" Bob and "Battling" Bob in early 1986 after the cast came off and fought Mr. T at Saturday Night's Main Event, which served as a setup for the Piper-Mr. T match at WrestleMania 2.
Piper and Orton went their separate ways after WrestleMania, with Piper taking a hiatus and Orton in the meantime becoming the bodyguard for Piper's talk-segment successor Adorable Adrian Adonis; Adonis had Orton wear a pink cowboy hat. When Piper returned later in 1986 to reclaim his talk show segment (turning face in the process), Orton betrayed his long-time friend, sparking a violent feud that typically saw Piper winning. During this time, Orton formed a tag team with The Magnificent Muraco, with the duo managed by Mr. Fuji. They won several matches and appeared at WrestleMania III, losing to the Can-Am Connection.
During the summer of 1987, Muraco and Orton began arguing during several of their matches, eventually with the two turning on each other. Orton continued to be billed as the heel while Muraco (adopting the nickname "The Rock") turned face. The two wrestlers feuded with each other during the late summer and early fall, after which Orton left the WWF.
On February 3, 2005, Bob Orton was announced as a 2005 inductee into the WWE Hall of Fame.
In the weeks preceding WrestleMania 21, Orton became entangled in his son Randy's feud with The Undertaker. During an episode of SmackDown!, Orton begged The Undertaker to show mercy on his son in order to distract The Undertaker long enough for his son to sneak into the ring and hit the RKO.[4] At WrestleMania, he (unsuccessfully) interfered in the match between Orton and The Undertaker, striking The Undertaker with his cast.[5]
On August 21, 2005, at SummerSlam, Orton interfered in a rematch between Randy and The Undertaker, this time enabling his son to defeat The Undertaker. Orton then began accompanying Randy to ringside during his matches, and teamed with his son at No Mercy on October 9, 2005, defeating The Undertaker in a handicap casket match. The Ortons teamed together once again on the October 28, 2005 episode of SmackDown!, joining forces with Ken Kennedy to face Roddy Piper, Batista, and Eddie Guerrero in a six man tag team match. The match ended in defeat for the Ortons when Orton succumbed to Piper's sleeper hold.
On the December 16, 2005 episode of SmackDown!, Orton disguised himself as one of the Undertaker's druids and carried The Undertaker's signature urn to ringside as The Undertaker came to the ring to confront Randy. Orton remained at ringside after the other druids had left, distracting The Undertaker and enabling Randy to attack him. Orton then handed Randy the urn, which Randy used to knock The Undertaker unconscious.
At Armageddon, Orton (still holding the urn) accompanied Randy to ringside for his Hell in a Cell match with The Undertaker. He interfered in the match several times, but was ultimately unable to prevent The Undertaker from delivering a Tombstone Piledriver to both Ortons and then covering Randy for the win.
On February 13, 2006, Orton was released from WWE.
Orton made an appearance on the November 15, 2010 episode of WWE Raw as the show went old school, with appearances from past WWE wrestlers, announcers and other on-air personalities. He also appeared on the April 10, 2012 episode of WWE SmackDown and was attacked by Kane (offscreen) who had been feuding with his son Randy at the time.