In 1984, Roberts entered World Class Championship Wrestling (WCCW) joining up with "Gentleman" Chris Adams and Gino Hernandez in their feud against the Von Erichs, winning the WCCW Television Title and 6-Man Tag Team title (with Adams and Hernandez).
Roberts debuted in the World Wrestling Federation in March 1986. A month later, he made his pay-per-view debut, defeating George Wells at WrestleMania 2. During the match, Roberts made Wells foam from the mouth when he wrapped his snake Damien around Wells's head.
Roberts' first major feud was against Ricky "The Dragon" Steamboat, beginning on a nationally televised episode of Saturday Night's Main Event VI in May 1986. Roberts executed the DDT on Steamboat on the exposed concrete floor right in front of his wife Bonnie and then proceeded to rest his snake Damien on top of a prone Steamboat. Unfortunately, Steamboat was unable to stop his head from hitting the concrete and was rendered unconscious, sustaining a concussion. After Steamboat's recovery, Steamboat introduced a "Komodo dragon" as his pet to combat the psychological effects of Roberts' snake. The feud continued with Steamboat winning most of the matches (losing only one because he threw Roberts back in the ring before the 10 count, while not beating the count himself), most notably a Snake Pit Match (ostensibly a no-DQ match) at The Big Event in Toronto, and the rematch on the October 1986 edition of Saturday Night's Main Event XII.
Recognizing his microphone skills, Roberts was given his own talk segment called "The Snake Pit", which debuted on the first episode of WWF Wrestling Challenge in late 1986. "The Snake Pit" was patterned after "Piper's Pit", wherein Roberts would conduct interviews with wrestlers or managers to help push wrestlers and get feuds over with the crowd. The segment was eventually moved to WWF Superstars of Wrestling (to replace "Piper's Pit" after Roddy Piper's retirement following WrestleMania III) until the final segment aired in July 1987.
In late 1986, Roberts began to enjoy an upsurge in fan popularity, despite the WWF's attempts to cast him as an unpopular villain. In November 1986, Roberts challenged Randy Savage for the Intercontinental Championship. Before the match, announcer Vince McMahon said the fans would probably support Savage against the disliked Roberts. However, to the surprise of both McMahon and fellow broadcaster Jesse "The Body" Ventura, the fans cheered loudly for Roberts throughout the bout. The match ended in a double disqualification. Around the same time, the WWF had also tried to set Roberts up as a nemesis to then fan-favorite WWF Heavyweight Champion Hulk Hogan. However, after Roberts hit Hogan with a DDT during an episode of The Snake Pit, fans responded positively to the attack by chanting "DDT" rather than for Hogan, and McMahon abandoned his plans for a feud between them.
He officially turned face when he feuded with The Honky Tonk Man, an Elvis impersonator, who attacked Roberts with a guitar during his interview segment The Snake Pit. The Honky Tonk Man's guitar shot actually injured Roberts' neck. The attack led to their match at WrestleMania III in which Roberts had Alice Cooper (a known lover of snakes) in his corner. After Honky Tonk won the Intercontinental Championship from Ricky Steamboat, Roberts unsuccessfully challenged him for the championship several times throughout the rest of 1987.
He then had a feud with "Ravishing" Rick Rude and his manager Bobby "The Brain" Heenan, who began a gimmick of selecting a woman from the crowd to kiss after each match. On the April 23, 1988 edition of WWF Superstars of Wrestling, Rude chose Roberts' wife Cheryl, who refused the kiss and revealed that she was in fact the wife of Jake "The Snake". After Rude began insulting Roberts, Cheryl slapped him, angering Rude before Roberts ran out for the save. This began a heated feud throughout the summer of 1988, which escalated after Rude began wearing a pair of tights emblazoned with a visage of Mrs. Roberts, which an irate Roberts tore off.
Roberts moved from the feud with Rude into a feud with André the Giant who was also managed by Bobby Heenan. On the March 11, 1989, episode of Saturday Night's Main Event XX, André got involved in a match between Rick Rude and Brutus "The Barber" Beefcake, siding with fellow Heenan Family member Rude. Roberts came to the ring to help Beefcake, who eventually won by disqualification. Roberts used his snake Damien to scare Andre into an eventual "heart attack." Although the subsequent feud on the house show circuit saw André victorious after most of those matches, Roberts can claim a victory via disqualification over André after The Giant attacked special guest referee and former foe Big John Studd at WrestleMania V.
Shortly after his feud with André had ended, Roberts entered into a feud with Ted DiBiase. Instead of fighting for the Intercontinental Championship, the prize of the feud was DiBiase's own Million Dollar Belt. It was at this time that Roberts' problems with the discs in his back 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 Virgil to reach into the canvas sack where Damien was to retrieve it. The culmination of their feud took place at WrestleMania VI at the Skydome in Toronto, where in a match where the Million Dollar Belt was on the line, DiBiase gained a count-out victory over Roberts, thus regaining his non-sanctioned title. After the match, Roberts mounted an offensive against DiBiase and Virgil and then began giving away DiBiase's "money" including giving some money to actress Mary Tyler Moore who was seated at ringside.
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 his cologne "Arrogance" 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 was able to "locate" Martel and deliver a DDT.
In early to mid-1991, Roberts engaged in a feud with Earthquake who "squashed" Damien with a pair of Earthquake splashes during their match on the April 27 (taped March 26) edition of WWF Superstars of Wrestling. The feud was advanced when, several weeks later, Earthquake appeared on WWF Prime Time Wrestling and served "Quakeburgers" to co-host Lord Alfred Hayes and Vince McMahon, later claiming that the meat was ground from Damien's carcass. Roberts later introduced a new snake, Damien's "big brother" Lucifer.
In the summer of 1991 there were a series of televised vignettes featuring the Ultimate Warrior turning to Roberts for help in his feud with The Undertaker. In the set-up, Roberts explained to Warrior that, after passing three tests, he would have the "knowledge of the dark side" to defeat Undertaker. The segments included Warrior being locked inside a coffin (a reprise of an incident that occurred on The Funeral Parlor, hosted by the Undertaker's manager, Paul Bearer; earlier in the year); the Warrior being "buried alive" in dirt before being abandoned; and Warrior walking through a room full of live snakes to reach a chest containing "the answer". During the latter segment, the Warrior opened the chest, only to be immediately bitten by a king cobra. 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; Roberts closed the final segment by proclaiming, "Never trust a snake", turning Roberts heel for the first time since 1987. A series of matches were planned, but the feud was canceled after the Ultimate Warrior was fired by the WWF the night of SummerSlam.
After SummerSlam, Roberts was placed in a feud with Randy Savage. During the post-SummerSlam wedding reception of Savage and Miss Elizabeth, Elizabeth opened a gift package containing a live cobra. Roberts and the Undertaker attacked Savage, until Sid Justice ran them off. A short feud with Sid ensued when Sid was scheduled to wrestle "El Diablo" and the Undertaker came out and accepted the challenge to face Sid. Paul Bearer offered "El Diablo" what appeared to be a bribe to walk away. As the match began, "El Diablo" came back to the ring and hit Sid. Then "El Diablo" unmasked revealing himself as Jake. Roberts proceeded to unleash a king cobra on Sid, until "Hacksaw" Jim Duggan intervened. Sid and Jake wrestled on Superstars a week later. But soon, Sid injured his biceps, which forced the feud to end.
Roberts immediately began berating Randy Savage in a series of promos, aware that Savage — who had lost a retirement match to the Ultimate Warrior at Wrestlemania VII — was unable to exact revenge. During an October 21 taping for WWF Superstars of Wrestling, Roberts goaded Savage into the ring and brutally attacked him, eventually tying Savage into the ropes and got the king cobra to bite his arm.
WWF president Jack Tunney reinstated Savage as an active wrestler to get revenge for the attack. To explain the absence of the cobra, 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 on December 3 in San Antonio, Texas, which saw Savage earn a victory over Roberts and Roberts slap Miss Elizabeth. The feud continued 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 XXX, 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 after the match), 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 Roberts was about to swing the chair, he was stopped by the Undertaker; Roberts was distracted long enough for Savage to hit him with the chair instead. That incident helped set up Roberts' feud with the Undertaker. Roberts appeared on The Funeral Parlor to demand answers from the Undertaker about why he stopped him from attacking Elizabeth. When Roberts was dissatisfied with the answers, he hit Bearer with a DDT and, after jamming Undertaker's hand in a coffin, began hitting him with a steel chair; however, Undertaker got up after each chair shot and eventually chased Roberts backstage dragging the coffin behind him. At WrestleMania VIII, Roberts lost the match, becoming the second man to lose to The Undertaker at WrestleMania.
The WrestleMania VIII match turned out to be Roberts' last for the WWF for nearly four years. He left the WWF soon after.
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 90 days.
Roberts made his first television appearance on August 2, 1992 at a Main Event taping in Baltimore, Maryland after coming through the crowd to attack Sting. His first WCW match came six days later when he defeated Marcus Alexander Bagwell on a house show in Chicago, Illinois. He would quickly form an alliance with Cactus Jack and The Barbarian. His first major TV wrestling appearance for WCW was at Clash of the Champions XX, 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 would be wrestling until the wheel stopped spinning. When the wheel stopped, it had landed on the Coal Miner's Glove match.
Following the loss to Sting he continued his feud, facing him on several house shows immediately after the event. On the November 2 episode of Saturday Night, Tony Schiavone conducted a sit-down interview with Roberts regarding the decision of Bill Watts to ban his bringing of the snake to ringside, and his impending first round match against Dustin Rhodes in the first round of the King of Cable tournament. He was replaced in the tournament by The Barbarian after leaving the company.
Roberts returned to WWF at the Royal Rumble in 1996, as a Bible preacher. To go along with his new gimmick, his new Albino Burmese Python was named "Revelations."
During his second tenure with the company, Roberts was pushed as a "Cinderella story" and faced Stone Cold Steve Austin in the final match of the 1996 King of the Ring tournament. Changes had to be made to the match's scripting as legitimate injuries sustained earlier in the evening in a match with Vader left Roberts unable to engage in the longer, more evenly matched bout originally intended between the men. In order to prevent Roberts from sustaining further injury, he was quickly defeated by Austin; in a post-match interview, Austin 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 John 3:16... Austin 3:16 says I just whipped your ass!". Roberts next feuded with Jerry "The King" Lawler, who went to great lengths to ridicule Roberts' past alcoholism.
He appeared at the 1997 Royal Rumble where he entered at number 7 and was eliminated by Stone Cold Steve Austin. His last match with WWF was on Shotgun Saturday Night on January 25, 1997 against Salvatore Sincere in a winning effort. He was released in February 1997.
During the summer of 1997, Roberts debuted in ECW. His introduction came towards the end of a match between Jerry Lawler and Tommy Dreamer, which was the main event of the show. As the match went on, the arena lights were turned off. Moments later when the lights came back on, Roberts was already in the ring, and proceeded to give Tommy Dreamer a clothesline. He promptly clotheslined Lawler, who fell onto Dreamer for a two count before exiting the ring.
Roberts also teamed with Tommy Dreamer at the 1998 November to Remember as his mystery partner against Justin Credible and Jack Victory.
Roberts made an appearance on March 14, 2005 on Raw, where he confronted Randy Orton, who was preparing to challenge The Undertaker at WrestleMania 21. Roberts warned Orton that facing The Undertaker, particularly at WrestleMania, could be a soul-altering experience; he then fell victim to Orton's "RKO," helping to fuel Orton's "Legend Killer" gimmick.
On January 6, 2014, Roberts made an appearance on the "Old School" episode of Raw, laying a python over the face of an unconscious Dean Ambrose. Roberts was announced as part of the 2014 Class of the WWE Hall of Fame. He was inducted by Diamond Dallas Page on April 5, 2014.