Flair signed with the World Wrestling Federation (WWF) in August 1991 and began appearing on television as one of the most hated heels the next month. Initially, he appeared on WWF shows with the "Big Gold Belt," calling himself "The Real World Champion." Led by his "financial advisor" Bobby Heenan and his "executive consultant" Mr. Perfect, Flair repeatedly issued challenges to WWF wrestlers like Roddy Piper and Hulk Hogan, wrestling a team led by Piper at Survivor Series in 1991 and helping The Undertaker defeat Hogan for the WWF Championship that same night.
At the Royal Rumble in 1992, he won the Rumble match to claim the vacant WWF Championship. Flair drew number three in the Rumble match and lasted a then-record nearly 60 minutes, last eliminating Sid Justice with help from Hulk Hogan, who had been eliminated by Justice seconds earlier.
After a planned program with Hogan was scrapped due to Hogan's hiatus following the WWF's steroid scandal, Randy Savage challenged Flair for the WWF title as part of the double main event at WrestleMania VIII. In the storyline, Flair taunted Savage by claiming that he had a prior relationship with Savage's wife, Elizabeth, and that he had the pictures to prove it (which were later revealed to be doctored photos). Savage defeated Flair for the title at WrestleMania. In July 1992, as Savage prepared to defend the title against The Ultimate Warrior at SummerSlam, Flair and Mr. Perfect sowed distrust between the two by suggesting that they would back one or the other during their match. They actually attacked both Savage and Warrior and injured Savage's knee, an injury that Flair exploited to regain the title in a match with Savage on September 1. His second reign was short-lived, however, as he lost the title to Bret Hart on October 12, 1992.
Flair teamed with Razor Ramon to take on Savage and Perfect at the Survivor Series 1992. After losing a Loser Leaves the WWF match to Mr. Perfect on the January 25, 1993 edition of Monday Night Raw, Flair appeared in the Royal Rumble in 1993 (although the match with Perfect had been taped six days prior, it did not air until the following night) and then fulfilled his remaining house show commitments, making his last appearance on February 10, 1993.
After hiatus from wrestling, Flair made a popular return to the WWF in November 2001 as the on-camera co-owner of the company and as a face in Charlotte on RAW in November 2001. Flair reappeared on Raw following the end of the "Invasion" that culminated in a "Winner Take All" match at Survivor Series won by the WWF. Flair's new on-screen role was that of the co-owner of the WWF, with the explanation that Shane and Stephanie McMahon had sold their stock in the company. Flair's feud with Vince McMahon led them to a match at the Royal Rumble in 2002 in a Street Fight, where Flair defeated McMahon. Flair also wrestled The Undertaker at WrestleMania X8 in 2002 where Flair lost after a hard fought battle and interference by Arn Anderson. From then, the "co-owner" angle culminated in early 2002, when Flair controlled Raw, and McMahon controlled SmackDown!. After Steve Austin abruptly left WWE while in a program with Flair, a match was hotshotted between Flair and Vince for sole ownership of WWE, which McMahon won, thanks to interference by Brock Lesnar.
Flair later became a villain by joining Triple H's "Evolution" stable. Flair won the World Tag Team Championship with Batista twice in 2003 and 2004. After HHH took time off following Vengeance and for the rest of the summer, Flair would become a fan favorite again by beginning a short feud with Kurt Angle. Later, at Unforgiven in 2005, Flair defeated Carlito for the Intercontinental Championship.
On the October 3 edition of Raw, Flair was attacked by his Evolution tag team partner Triple H, after Triple H threw him into a limousine and smashing into limousine window for using sledge hammer. On November 1, 2005 at Taboo Tuesday, Flair defeated Triple H in a steel cage match. Flair continued his feud with Triple H until Survivor Series, when Triple H defeated him in a Last Man Standing match to end the feud.
At the end of 2005 Flair had a feud with Edge, culminating in a WWE Championship TLC match on Raw in early 2006. On the February 20 edition of Raw he lost to Shelton Benjamin. Flair then took some time off in mid-2006 to rest; he returned in June to work a program with Mick Foley. Flair defeated Foley at SummerSlam in an "I Quit" match.
Subsequently, he was involved in a rivalry with the Spirit Squad on Raw. On November 5, 2006 at Cyber Sunday, he captured the World Tag Team Championship from the Squad with Roddy Piper. On the November 13 edition of Raw, Flair and Piper lost the Tag Titles to Rated-RKO, due to a disc problem with Piper and had to be flown immediately back to the USA as soon as Raw was off the air. On November 26, 2006 at Survivor Series, Flair was the sole survivor of a match that featured himself, Ron Simmons (replacing an injured Piper), Dusty Rhodes and Sgt. Slaughter versus the Spirit Squad. Flair then left television due to personal reasons. On the December 11, 2006 edition of Raw, Flair returned to team up with DX again. They defeated Rated-RKO and Kenny Dykstra.
Flair then began teaming with Carlito after Flair said that Carlito had no heart. Flair defeated Carlito in a match after which Carlito realized that Flair was right. Flair and Carlito faced off against Lance Cade and Trevor Murdoch in a number one contender's match for the World Tag Team Championship but were defeated. The two teamed up at WrestleMania 23, and defeated the team of Chavo Guerrero and Gregory Helms. After weeks of conflict between Flair and Carlito, the team split up when Carlito attacked Flair during a match. At Judgment Day, Flair defeated Carlito with the figure four leglock. His career was put at risk following a match with Randy Orton on June 4, 2007.
On the June 11 edition of Raw, Flair was drafted from Raw to SmackDown! as part of the 2007 WWE Draft. He briefly feuded against Montel Vontavious Porter and rejoined forces with Batista to feud with The Great Khali; the alliance was short-lived, however, as Flair was "injured" during a match with Khali.
After three month hiatus, Flair returned to WWE programming on the November 26 edition of Raw to announce "I will never retire". Vince McMahon retaliated by announcing that the next match Flair lost would result in a forced retirement. Later in the night, Flair defeated Orton after a distraction by Chris Jericho. It was revealed on the 15th anniversary of Raw that the win or retire ultimatum only applied in singles matches. Flair won several "career threatening" matches against the opponents such as Triple H, Umaga, William Regal, Mr. Kennedy, and Vince McMahon himself among others. On March 29, 2008, Flair was inducted into the WWE Hall of Fame as a part of the Class of 2008 by Triple H. Flair became the first active wrestler to be inducted into the Hall Of Fame. The day after, Flair wrestled at WrestleMania XXIV in Orlando, Florida, losing to Shawn Michaels.
On the March 31, 2008 edition of Raw, Flair delivered his farewell address. Afterward, Triple H brought out many current and retired superstars to thank Flair for all he has done, including Shawn Michaels, some of the Four Horsemen, Harley Race, and Chris Jericho, followed by The Undertaker and then Vince McMahon. Along with the wrestlers, the fans gave Ric a standing ovation.
Flair made his first post retirement appearance on the June 16, 2008 edition of Raw to confront Chris Jericho about his actions during a rivalry with Shawn Michaels. He challenged Jericho to a fight in the parking lot, rather than an official match, but was ejected from the building by Vince McMahon. The following year on February 9 Flair once again confronted Chris Jericho on Raw. Jericho was attacking Hall of Fame members and Flair demanded he respect them, before punching Jericho. Flair appeared a month later to distract him during a Money in the Bank Qualifying Match. Jericho then challenged Flair to come out of retirement for WrestleMania XXV; instead Flair managed Roddy Piper, Jimmy Snuka and Ricky Steamboat in a three-on-one handicap match at WrestleMania in a losing effort.
On May 17 Flair returned to WWE during the Judgment Day pay-per-view, coming to the aid of Batista, who was being attacked by The Legacy (Randy Orton, Cody Rhodes and Ted DiBiase). On his last appearance in WWE, on the June 1 episode of Raw, Flair challenged Randy Orton in a parking lot brawl match, after an interference from the rest of The Legacy, the fight ended with Flair was trapped inside a steel cage and was punted by Orton. After Raw, Flair left WWE when his contract expired on June 2, 2009.
On March 31, 2012, Flair became the first person to be inducted into the WWE Hall of Fame twice, the second time as part of the Four Horsemen.
On December 17, Flair returned to WWE on the annual Slammy Awards show to present the 'Superstar of the Year' award to John Cena, who in turn gave the award to Flair. While speaking to the crowd, Flair was interrupted by the former WWE Champion CM Punk and Paul Heyman, and subsequently challenged the champion to a fight in the ring and locked Heyman in the Figure Four Leg Lock. After clearing the ring Flair was interrupted and assaulted by The Shield, until Team Hell No (Kane and Daniel Bryan) made their way out to even the sides. As the Shield attempted to hit a triple powerbomb on Flair through the announcer's table, Ryback came out to save Flair and assist in countering the Shield. Kane, Bryan and Ryback then paraded Flair around the ring to a standing ovation. On January 14, 2013, Flair returned on the Raw 20th Anniversary special, as a guest on Miz TV. The Miz and Flair were interrupted by Antonio Cesaro, but Flair knocked Cesaro down with a few of his signature chops, and once down let The Miz use his signature figure-four leg lock on Cesaro. Miz has since adopted the move as his finisher. Flair's next appearance on WWE TV was on the March 4 "Old School" edition of Raw. He appeared in Miz's corner during his match with Dolph Ziggler and got in a physical confrontation with Big E Langston, a member of Ziggler's entourage. On the July 17 episode of NXT, Flair accompanied his daughter Charlotte for her debut match which resulted in a winning effort. He made an appearance on Old School Raw on January 6, 2014 with other former Evolution member Randy Orton confronting Flair. Flair appeared on the April 28 Raw, alongside the reunited Evolution (sans Flair) and The Shield. Flair showed his endorsement for the Shield, Evolution's opponents at Extreme Rules, effectively turning his back on his old teammates. On May 29, 2014, at NXT Takeover, he accompanied Charlotte, and with the aid of the referee (Charles "Lil Naitch" Robinson), crowned her the new NXT Women's Champion.
On July 14, 2014, Flair appeared on Raw to promote John Cena in his upcoming match at Battleground. Cena symbolically handed over his World Heavyweight Championship title belt to Flair, telling him to "take it". On August 11, Flair appeared on Raw taking part in Hulk Hogan's birthday bash.
On the January 19, 2015 episode of Raw, Flair participated in a "legends panel" alongside Shawn Michaels and Hulk Hogan on the "Raw Reunion Show". Flair predicted that Dean Ambrose would win the 2015 Royal Rumble match, and afterwards, was interrupted by the Big Show. Flair was then knocked out by Show after chopping and punching at him. On the August 24, 2015 episode of Raw, Flair came out and interrupted Jon Stewart, who the previous night had saved Flair's 16 world title record in the winner takes all match, with Flair telling Stewart that the record will be broken eventually and he'd rather it would be by someone who he respects. Flair appeared on the September 15th, 2015 episode of "Raw", celebrating with daughter Charlotte after her WWE Divas Championship 'victory'. Six days later Charlotte won the Divas Champion on Night of Champions where he was there. The following night on Raw he did a segment in ring celebrating Charlotte's victory with Team PCB (Paige, Charlotte and Becky Lynch) where Paige turned heel. On December 13 at TLC, Ric Flair helped her daughter retain her title by placing Charlotte's foot on the rope as she was being pinned, effectively turning both Flair and Charlotte heel. On the May 23, 2016, episode of RAW, Flair turned face again when Charlotte betrayed him by ordering him to get out of the ring, but not before chastising him for not being there for most of her childhood. On the November 28, 2016 episode of Raw, Flair returned to congratulate the new Raw Women's Champion Sasha Banks that had just defeated Charlotte (who started to being referred as Charlotte Flair more often) to win the title.
