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Roberts' first major feud was against Ricky "The Dragon" Steamboat. The feud began on a nationally televised episode of Saturday Night's Main Event in May 1986. Roberts executed the DDT on Steamboat on the floor right in front of his wife, Bonnie, whom Roberts had pointed to just before delivering the blow and then proceeded to rest his snake Damien on top of a prone Steamboat. Roberts went so far as to put the snake in Steamboat's mouth. He later stated that he was initially against doing the angle for fear that he might seriously injure or kill Steamboat. While Vince McMahon and booker George Scott were adamant about wanting the DDT to take place on the floor, he refused until Steamboat told him that he would be able to adequately protect himself from injury. Steamboat was rendered unconscious and sustained a concussion. After Steamboat's recovery, the feud featured Steamboat introducing a "Komodo dragon" (actually a small alligator) as his "pet" to combat the psychological effects Roberts' reptilian counterpart had on most adversaries. The feud continued with Steamboat winning most of the matches (losing only one and because he threw Roberts back in the ring before the 10 count, then not beating said count himself), most notably a Snake Pit Match (obstensibly a no-DQ match) at The Big Event in Toronto, and the rematch on the October 1986 edition of Saturday Night's Main Event. Since their feud ended, both men have cited tremendous respect for one another, stating that the feud was a personal favorite for both. When asked about "The Dragon" in an interview, Roberts stated, "[Steamboat] was a great wrestler, but an even better man."

In November 1986, Roberts challenged Randy "Macho Man" Savage for the Intercontinental Championship in a nationally televised match. Before the match, announcer Vince McMahon stated that the fans would probably support Savage against the disliked Roberts. However, to the surprise of both McMahon and fellow broadcaster Jesse Ventura, the fans cheered loudly for Roberts throughout the fight. The match ended in double disqualification. Around this time, the WWF was trying to get a feud between Roberts and Hulk Hogan going, but after Roberts DDTed Hogan during an episode of The Snake Pit, too many people started chanting for the DDT rather than for Hogan, forcing them to step away from this like it never happened. This also may have contributed to Robert's eventual face turn.

He officially turned face when he feuded with The Honky Tonk Man, a heel with an Elvis impersonator gimmick. The Honky Tonk Man attacked Roberts with a guitar during his interview segment The Snake Pit. In reality, The Honky Tonk Man's guitar shot legitimately injured Roberts' neck. The shot was prior to the use of gimmicked breakable guitars, so it caused a legitimate injury. The Honky Tonk Man denies that he legitimately injured Roberts, although Jimmy Hart, as well as a video of the incident (seen on the Pick Your Poison DVD) suggests otherwise. The attack led to their match at Wrestlemania III in which Roberts had Alice Cooper in his corner. He would go on to unsuccessfully challenge The Honky Tonk Man for the Intercontinental Championship several times throughout the rest of 1987. The initial plan was for Roberts to win the Intercontinental Championship shortly after The Honky Tonk Man's win over Ricky Steamboat and begin an angle with the Million Dollar Man Ted Dibiase, but because of the injuries he suffered from the guitar shot, the decision was made to keep the belt with The Honky Tonk Man.

Perhaps his best-known feud was against "Ravishing" Rick Rude, who used to select a woman from the audience to kiss after each match. Rude chose Roberts' real-life wife Cheryl, who refused the kiss; Roberts rescued her before Rude could attack, Cheryl slapped him rather hard. This was staged and Rude began an angle with Roberts. At another event, Rude wore a pair of tights emblazoned with a visage of Mrs. Roberts, (another act that was not sanctioned by WWF at the time and was Rude's own brainchild) which an irate Roberts tore off. Many believe this angle was far ahead of it's time, a precursor to the Attitude Era.

Next, Roberts engaged in a feud with André the Giant after being eliminated by André at the 1989 Royal Rumble. In this storyline, Roberts used his snake to gain a psychological edge over the snake-averse André (who as part of the angle staged a heart attack on national television), to nullify the Giant's overwhelming size and strength advantage. Roberts can claim a victory via disqualification over André after André attacked special guest referee Big John Studd at WrestleMania V.

Shortly after his feud with André had ended, Roberts entered into a feud originally scheduled to happen years before with Ted DiBiase. Instead of fighting for the Intercontinental Championship, the prize of the feud was Dibiase's Million Dollar Belt. It was at this time that Roberts' disc problems were publicly acknowledged, as DiBiase attacked Roberts after a victory over his bodyguard Virgil on WWF Superstars of Wrestling. In the attack, Roberts was (storyline) injured by DiBiase and needed time off to have surgery to repair the damage. Roberts returned and feuded with DiBiase throughout the end of 1989 into 1990, including a point where Roberts stole Dibiase's Million Dollar Belt, daring him or then-heel, Virgil to reach into the canvas sack to retrieve it. The culmination of their feud took place at WrestleMania VI, where in a match where the Million Dollar Belt was on the line, DiBiase gained a count-out victory over Roberts, thus regaining the non-sanctioned title. After the match, Roberts mounted an offensive against DiBiase and Virgil and then began giving away DiBiase's "money".

Following a brief feud with Bad News Brown in the summer of 1990, Roberts feuded with Rick "The Model" Martel throughout late 1990 into early 1991, after Martel (kayfabe) blinded Roberts by spraying cologne into his eyes. Roberts went so far as to wear white contact lenses to "prove" his blindness. After several months, the feud culminated in a match at WrestleMania VII, in which both contestants were blindfolded. The bout ended after Roberts beat Martel with a DDT.

In early to mid-1991, Roberts engaged in a feud with Earthquake after he "squashed" Damien (in actuality, it was hamburger stuffed in pantyhose with a small motor to make it look like a live snake was in the bag), and then used Damien's "carcass" to make "Quakeburgers", which he fed to on-air commentator Lord Alfred Hayes. Roberts appeared on Brutus "The Barber" Beefcake's interview segment The Barbershop and stated that "You could do two things: Roll over and die, or get yourself a bigger snake", in which he revealed that his new snake was a larger python, a reticulated python whom he named "Lucifer"—the supposed big brother of Damien and "the devil himself."

In mid-1991 Roberts was the one the Ultimate Warrior turned to in his feud with the heel gimmick of The Undertaker. The angle involved Roberts telling the Warrior that he would have the knowledge of the dark side necessary to defeat his adversary after passing three tests, which would be shown on WWF TV in consecutive weeks. The first was to be locked inside of a coffin, repeating an incident that occurred on The Funeral Parlor (which was hosted by the Undertaker's manager then-heel, Paul Bearer), a few months prior. The second test had Roberts "bury" the Warrior alive in dirt and walk off-screen. The third test involved Warrior entering a room full of snakes and having to walk through them to find "the answer" in a chest in the middle of the room. When the Warrior opened the chest, he was alarmed to find a King Cobra, which bit him in the face; in actuality, the snake was a rubber prop. As Warrior "weakened" from the "effects" of the cobra's strike, Roberts was joined by The Undertaker and Paul Bearer, revealing the three were working together all along with Roberts telling Warrior "Never trust a snake." The feud was quickly canceled after the Ultimate Warrior was fired by the WWF the night of SummerSlam in 1991.

Afterward, Roberts became a heel again and had a feud with "Macho Man" Randy Savage after he interrupted Savage's wedding reception by putting a snake in one of the gift boxes at SummerSlam and later used a (de-venomed) cobra to bite Savage's arm. According to Roberts' DVD Pick Your Poison, he had trouble getting the cobra to release his bite. The segment went on longer than planned, and Savage's blood was clearly visible, dripping from the puncture wounds. WWF president Jack Tunney reinstated Savage, who had lost a retirement match (to the Ultimate Warrior) earlier that year at WrestleMania VII, as an active wrestler to get revenge for the attack. To explain the absence of the cobra in kayfabe, Tunney "banned" Roberts from ever bringing a snake to the ring again. Savage and Roberts feuded for the next few months. Their first match was at the Tuesday in Texas pay-per-view, which saw Savage earn a victory over Roberts, but it was Roberts attacked Savage after the match and slapped his wife, Miss Elizabeth, in the middle of the ring. The feud would continue through the early part of 1992, and included Savage eliminating Roberts from that year's Royal Rumble match. The feud ended on Saturday Night's Main Event, with Savage getting the win. Roberts, livid at having lost to him and having received two of Savage's flying elbow drops (one of which happened after the match; Savage was going for a third until officials intervened), was helped backstage. Enraged, he grabbed a steel chair and said that he was going to hit whoever came backstage first, whether it was Savage or Elizabeth. Just as he was about to swing the chair, someone stopped him. While Savage and Elizabeth, seeing they had averted a potential attack, stalled, Roberts turned to confront the Undertaker, who distracted Roberts long enough so that Savage could hit him with a chair instead.

This incident turned the two partners against each other. On The Funeral Parlor, Roberts locked the Undertaker's hand in a casket and DDT'ed the show's host and Undertaker's manager Paul Bearer, before hitting the Undertaker repeatedly with a steel chair. This would also make Undertaker and Bearer turn face. At WrestleMania VIII, Roberts was defeated by the Undertaker. He left the WWF soon after that, upset that WWF chairman Vince McMahon did not offer him a position on the writing staff, despite being promised such previously. After Pat Patterson stepped down from his post on the writing staff, McMahon decided that out of respect for Patterson, the spot would be left vacant. Roberts felt he was not only being lied to, but also being betrayed. In response, he threatened to no-show WrestleMania if he was not given a release from his contract.

Roberts went on to work for World Championship Wrestling (WCW) alongside his father, Grizzly Smith, where he aligned himself with The Barbarian and Cactus Jack to feud against Sting and Nikita Koloff. However, before he could officially join WCW, he had to wait almost 90 days. According to the Pick Your Poison DVD, Roberts had initially signed a lucrative contract under Kip Allen Frey, who was running WCW at the time. On the 87th day, Frey stepped down and was replaced by Bill Watts, for whom Roberts had legitimate heat with back in his days at Mid-South Wrestling. Ultimately, Roberts estimates that he went from making about $3.5 million a year to approximately $200,000 a year.

His first major TV wrestling appearance for WCW was at Clash of the Champions, where his team won a 4-man elimination tag match. Roberts scored a pinfall victory over Sting, which built their feud further. His single WCW pay-per-view match was against Sting at Halloween Havoc in 1992. Their match was determined via the Spin the Wheel, Make the Deal gimmick. There was a series of gimmick matches on the wheel, but because the wheel itself was not gimmicked, neither Roberts nor Sting knew the kind of match they'd be wrestling until the wheel stopped spinning. When the wheel stopped, it had landed on what many pundits believed was the worst option—the Coal Miner's Glove match. However, it was the company's top-selling PPV for several years, but Roberts soon left WCW.

Roberts returned to WWF at the Royal Rumble in 1996, as a Bible-preaching face. To go along with his new gimmick, his new Albino Burmese Python was named "Revelations." His gimmick also mirrored his real life, as Roberts had recently become a born-again Christian and had been preaching around the country.

During his second tenure with the company, Roberts was pushed as a "Cinderella story" and faced then-heel, "Stone Cold" Steve Austin in the final match of the King of the Ring tournament. Due to injuries received at the hands of Vader in their semi-final match that night, Austin easily defeated him and mocked his recital of the biblical passage John 3:16 by saying "You sit there, and you thump your Bible, and you say your prayers, and it didn't get you anywhere... Talk about your Psalms, talk about your John 3:16 ... Austin 3:16 says I just whooped your ass!".[5] The catch phrase would help propel Austin to the top of the WWF and pro wrestling throughout "The Attitude Era" of the late 1990s to early 2000s. Roberts next feuded with then-heel, Jerry "The King" Lawler, who went to great lengths to ridicule Roberts' past bouts against alcoholism. At one point, Lawler spat real whiskey at Roberts.In November 1996, Roberts, Vader, and Brother Love appeared on the ABC sitcom Boy Meets World for one episode. In early 1997, the WWF wanted Roberts to wind down his in-ring career and to join the backstage side of the company. Since he still loved to wrestle, he did not make this transition well. This led to a relapse with drugs and alcohol. He was fired in February 1997. According to the Pick Your Poison DVD, after his firing, his long-time wife Cheryl filed for divorce.

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