Throughout his career, Roberts, often considered one of professional wrestling's most iconic figures, was known for his intense and cerebral promos, dark charisma, extensive use of psychology in his matches, and innovative use of the DDT finishing move (which was later named the "coolest" maneuver of all time by WWE).

In 2012, he moved in with fellow wrestler Diamond Dallas Page to seek help in getting his life back on track following years of alcohol and drug addiction, a period covered in the 2015 documentary The Resurrection of Jake the Snake.

Roberts returned to Mid-South Wrestling for 1985, ending his run there in February 1986 with a feud with Dick Slater after being told by management that he was not considered a top talent even though he was getting the biggest crowd reactions.

[11] 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.

While Vince McMahon and booker George Scott were adamant about wanting the DDT to take place on the floor, Roberts initially refused until Steamboat told him that he would be able to adequately protect himself from injury.

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.

He officially turned face when he feuded with The Honky Tonk Man, an Elvis impersonator, who attacked Roberts[14]with a guitar during his interview segment The Snake Pit.

[16] 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.

The culmination of their feud took place at WrestleMania VI at the Skydome in Toronto, wherein 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.

The feud continued through the early part of 1992 and included Savage eliminating Roberts from that year's Royal Rumble match for the vacant WWF World Heavyweight Championship.

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.

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.

[30] 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.

After doing such things as pretending his snake was a penis and stroking it like he was masturbating and attempting to kiss the snake with his tongue, the show's promoter sent King Kong Bundy and Yokozuna, who were supposed to compete in the other main event match, to the ring and made the main event a tag team match with Roberts teaming with Yokozuna against Bundy and Neidhart.

Roberts made his final British appearance at WAW's October Outrage show in Canvey Island, Essex, once again teaming with Steve Quintain against the UK Pitbulls.

Roberts cut a drunken promo paying tribute to Ray Traylor, who had died a few days before, and almost got into a scuffle with several WAW wrestlers who were sent out to defuse the situation.

Advertised as "a grueling 40 city campaign" containing pretty girls, wrestling, amazing circus stunts, and a fist fight, the tour features Jim Rose and wrestler Sinn Bodhi as "Team Jake".

[35] On March 15, 2014, Roberts debuted in Regional Championship Wrestling's Rumblemania 9 in Reading, Pennsylvania as a surprise partner for Cliff Serenyi against Russian Mafia with Rich Rogers.

[40] Roberts made a one-night return to TNA in 2008 as a guest of "Black Machismo" Jay Lethal and SoCal Val's storyline wedding at Slammiversary.

[44] In 2019 during The Road to All Out, Roberts appeared as a dealer at a blackjack table dealing cards to Women's Casino Battle Royale participants, referring to his infamous "you wanna play 21?"

[47] Archer was announced as a participant for the tournament for the AEW TNT Championship;[48] he defeated Colt Cabana in the quarter finals, and Dustin Rhodes in the semi-finals.

In a press release, their roles were explained as "they will bring their experience and passion for community relations to help identify partner organizations across the country, assist in incorporating talent participation and provide counsel on enhancing activations.

"[54] On the October 8, 2024 episode of Dynamite, Roberts acquired La Facción Ingobernable (Rush, Dralístico, and The Beast Mortos) from Don Callis in exchange for Lance Archer.

[56] Once he reached the World Wrestling Federation (WWF) in March 1986, he would bring a Burmese python (most were named "Damien") to ringside in a canvas bag.

Roberts also stated that director Barry Blaustein and Terry Funk lied to him about the aims of the film, telling him it was a television special on the effects of drug and alcohol abuse.

Roberts was featured in another wrestling documentary in 2015 entitled The Resurrection of Jake the Snake, which chronicled his time living with Diamond Dallas Page beginning in October 2012.

[7] Roberts appeared as Mr. Lucas, the owner of a gourmet condom company, in the comedy film, The Bet which also featured Dallas Page and Roddy Piper.

He revealed in 2023 that it was the product of an accident in the ring involving a fight with former Olympian Bob Roop, in which he dropped a knee on Roberts' throat and accidentally crushed his voice box.

[63] In October 2012, while financially distressed and having resumed abusing alcohol and drugs, Roberts moved in with former wrestler Diamond Dallas Page in Atlanta, Georgia, a time which was chronicled in the documentary The Resurrection of Jake the Snake.

In August 2014, Roberts fell ill during a flight from Atlanta to Las Vegas, where he was scheduled to attend a birthday event for fellow wrestler Nick Cvjetkovich.