Conflicts with Vince Russo and departure (1999–2000)

He then lost the title to Ric Flair at Uncensored in a Steel Cage First Blood match. A heavily bleeding Flair won via pinfall thanks to biased referee Charles Robinson. During that match, however, Hogan began to show some signs that a face turn was imminent, showing off some old tactics like his "Hulking up" no-sell. On the July 12 edition of Nitro, Hogan made his grand return as a full-fledged face and accepted a challenge from Savage, who had gained the world title at Bash at the Beach the night before. Thanks to interference from Nash, who had lost the title to Savage, Hogan defeated Savage to win his sixth and final WCW World Heavyweight Championship. On August 9, 1999, he started the night dressed in the typical black and white, but after a backstage scene with his son, Hogan came out dressed in the traditional red and yellow for his main-event 6-man tag team match. Injuries and frustrations were mounting up however, and he was absent from television from October 1999 to February 2000. In his book Hollywood Hulk Hogan, Bollea said that he was asked to take time off by newly hired head of creative booker Vince Russo and was not told when he would be brought back at the time. Despite some reservations, he agreed to do so. On October 24 at Halloween Havoc, Hogan was to face Sting for the WCW World Heavyweight Championship (which he had lost to Sting at Fall Brawl the previous month, when Sting beat Hogan by cheating and had turned heel in the process). Hogan, however, came to the ring in street clothes, laid down for the pin, and left the ring. Soon after his return in February 2000, at Bash at the Beach, Hogan was involved in a controversial, real-life incident with Vince Russo. Hogan was scheduled to wrestle Jeff Jarrett for the WCW World Heavyweight Championship. Before the match, there was a dispute between Hogan and Russo. Unbeknownst to Hogan, Russo told Jarrett to lie down in the middle of the ring and asked Hogan to pin him straight away. A visibly confused Hogan complied with a foot on Jarrett's chest after getting on the microphone and telling Russo, "Is this your idea, Russo...? That's why this company is in the damn shape it's in, because of bullshit like this!" Russo responded by coming out and saying that "From day one, that I've been in WCW, I've done nothing... nothing... but deal with the bullshit of the politics behind that curtain." Since Hogan refused to job to Jarrett, a new WCW World Heavyweight Championship was created, setting the stage for a title match between Booker T and Jeff Jarrett later that night. Whether or not the whole incident was a shoot or a work is still a hot debate. As a result, Hogan filed a defamation of character lawsuit against Russo soon after, which was eventually dismissed in 2002. Russo claims the whole thing was a work, and Hogan claims that Russo made it a shoot. Eric Bischoff agreed with Hogan's side of the story when he wrote that Hogan winning and leaving with the title was a work, and that he and Hogan celebrated after the event over the success of the angle, but that Russo coming out to fire Hogan was an unplanned shoot which led to the lawsuit filed by Hogan.

New World Order (1996–1998)

Main article: New World Order (nWo) This would come to fruition, as the stable, known officially as the New World Order (nWo), would gain prominence in the coming weeks and months. Hogan grew a beard alongside his famous mustache and dyed it black, traded his red and yellow garb in for black clothing, renamed himself Hollywood Hogan, and returned to WCW programming eight days after his heel turn.Around this time, he began to use his celebrity status and wrestling clout to bring in various celebrities, such as Karl Malone and Dennis Rodman into wrestling.A lot of people don’t consider wrestlers real athletes, you know, and we’ve had people like Bill Kazmaier and John Matuszak, and Lyle Alzado, Kevin Green - and everybody else. Dennis Rodman and Karl Malone, all try to get in the wrestling business. And... for some reason or not, decided that it was a little too hard or too many injuries, or it wasn’t for them. So I don’t know what you would classify as a real athlete just because of the genre that you’re in. ” Hogan won his second WCW World Heavyweight Championship at Hog Wild, defeating The Giant for the title. He spray painted a black "nWo" across the title belt, scribbled across the nameplate, and referred to the title as the "nWo title" during this and any other time he held the title while in the nWo. Hogan then started a feud with Lex Luger after Luger and The Giant defeated Hogan and Dennis Rodman in a tag team match at Bash at the Beach.[89] On the August 4, 1997 edition of Nitro, Hogan lost the WCW title to Luger by submission via Luger's Torture Rack submission finisher. Five days later, at Road Wild, Hogan defeated Luger to regain the WCW title and begin his third WCW World Heavyweight Championship.[52][98][99] Hogan then lost the belt to Sting in a hugely-hyped, eighteen-months-in-the-making match at Starrcade. In the match, WCW's newly-contracted Bret Hart accused referee Nick Patrick of fast-counting a victory for Hogan and had the match restarted—with himself as referee. Sting later won by submission. After a rematch the following night, where Sting controversially retained the title, the WCW Championship became vacant.[10] Sting then went on to win the vacant title against Hogan at SuperBrawl VIII.[101] Hogan then developed a rivalry with former friend (and recent nWo recruit) Randy Savage, who had just cost Hogan the title match at SuperBrawl by hitting him with a spray can. The heat culminated in a steel cage match at Uncensored, which ended in a no contest. Savage took the World Championship from Sting at Spring Stampede, while Hogan teamed with Kevin Nash to take on Roddy Piper and The Giant in the first-ever Bat match.[103] Marking the breakup of the original nWo, Hogan betrayed Nash by hitting him with the bat and then challenged Savage the following night for his championship. In the no disqualification match for Savage's newly won title, Nash entered the ring and powerbombed Hogan as retribution for the attack the previous night, and Bret Hart turned heel by jumping in to attack Savage and preserve the victory for Hogan, who regained his fourth WCW World Heavyweight Championship.[104][105] Hogan defended the title until July of that year, when WCW booked him in a match against newcomer and then WCW United States Champion Bill Goldberg, who had yet to lose a match in the company. Late in the match, Hogan was distracted by Karl Malone, who delivered a Diamond Cutter to nWo member Curt Hennig, the latter of whom was approaching the ring to assist Hogan. A spear and a Jackhammer from Goldberg then followed, and the rookie pinned Hogan to win his first and only WCW World Heavyweight Championship.[106] Hogan spent the rest of 1998 wrestling celebrity matches. His second tag team match with Dennis Rodman pitted them against Diamond Dallas Page and Karl Malone at Bash at the Beach and at Road Wild, he and Eric Bischoff lost to Page and Jay Leno thanks to interference from Kevin Eubanks, who leveled Bischoff with a Diamond Cutter. Hogan also had a highly hyped rematch with the Ultimate Warrior at Halloween Havoc, where his nephew Horace aided his victory. On the Thanksgiving episode of The Tonight Show with Jay Leno, Hogan officially announced his retirement from professional wrestling, as well as his candidacy for President of the United States.[110] Campaign footage aired on Nitro of Hogan and Bischoff holding a press conference, making it appear legitimate. In the long run, however, both announcements were false and merely done as a publicity stunt attempting to draw some of the hype of Jesse Ventura's Minnesota gubernatorial win back to him. After some time off from WCW, a still "retired" Hogan returned on the January 4, 1999 edition of Nitro to challenge Kevin Nash for the WCW title. He controversially regained his fifth WCW World Heavyweight Championship in what was later dubbed the Fingerpoke of Doom. This reformed the divided nWo branches—nWo Hollywood and nWo Wolfpac—which began feuding with Bill Goldberg and The Four Horsemen.