Ric Flair

On December 10, 1972, Flair made his American Wrestling Association (AWA) debut in Rice Lake, Wisconsin, battling George "Scrap Iron" Gadaski to a 10-minute draw. During his time in the American Wrestling Association, Flair had matches with Dusty Rhodes, Chris Taylor, André the Giant, Larry Hennig and Wahoo McDaniel.

In 1974, Flair left the AWA for World Championship Wrestling (WCW) and he soon captured his first singles title, when on February 9, 1975 he beat Paul Jones for the WCW TV Championship. Flair resumed his feud with Wahoo McDaniel in February 1976. Flair won the WCW United States Heavyweight Championship when he defeated Bobo Brazil on July 29, 1977. During the next three years, he held five reigns as WCW United States Heavyweight Champion while feuding with Ricky Steamboat, Roddy Piper, Mr. Wrestling, Jimmy Snuka and Greg Valentine (with whom he also formed a championship tag team). However, Flair reached elite status when he began referring to himself as "The Nature Boy" in order to incite a 1978 feud with the original "Nature Boy" Buddy Rogers, who put Flair over in one encounter.

On September 17, 1981, Flair beat Dusty Rhodes for his first WCW World Heavyweight Championship. In the following years, Flair established himself as the promotion's main franchise. Harley Race won the WCW World Heavyweight Championship from Flair in 1983, but Flair regained the title at Starrcade in a steel cage match. Officially, Flair won the WCW World Heavyweight Championship eight more times. Flair lost the title to Race and won it back in the span of three days in New Zealand and Singapore in March 1984. At the first David Von Erich Memorial Parade of Champions at Texas Stadium, Flair was pinned by Kerry Von Erich, but he regained the title eighteen days later in Japan and reigned for two years, two months and two days, losing the title to Dusty Rhodes on July 26, 1986 at The Great American Bash. However, Flair regained the title two weeks later.

In late 1985, the tag team of Arn Anderson and Ole Anderson began aiding Flair (whom they claimed as a "cousin") in attacks against Dusty Rhodes, Magnum T.A. and Sam Houston. A few weeks later, the Andersons interrupted Houston's match against Tully Blanchard and the three villains combined to rough up the youngster. Shortly thereafter, Flair, Blanchard and the Andersons formalized their alliance, calling themselves The Four Horsemen, with Blanchard's manager J.J. Dillon also coming on board. Upon the group's inception, it was clear that The Four Horsemen were unlike any villainous alliance that had ever existed, as the four rule breakers immediately used their strength in numbers to decimate WCW's top fan favorites while controlling the majority of the championship titles. Flair lost the WCW World Heavyweight Championship in Detroit to Ron Garvin on September 25, 1987. Garvin held the title for two months before losing to Flair on November 26, 1987, at WCW's first pay-per-view event, Starrcade, in Chicago.

In early 1988, Sting and Flair fought to a 45-minute time-limit draw at the first ever *Clash of the Champions*. On February 20, 1989, at Chi-Town Rumble in Chicago, Ricky Steamboat pinned Flair to win the WCW World Heavyweight Championship. This prompted a series of rematches, where Steamboat was presented as a "family man" (often accompanied by his wife and young son), while Flair opposed him as an immoral, fast-living "ladies man". Following a best-of-three falls match with Steamboat that lasted just short of the 60-minute time limit (and ended with a disputed finish where Steamboat retained the title) at *Clash of the Champions VI: Ragin' Cajun* on April 2, Flair regained the title from Steamboat on May 7, 1989, at WrestleWar. On July 23, 1989, Flair defeated Terry Funk at The Great American Bash, but the two continued to feud through the summer and eventually Flair reformed The Four Horsemen, with the surprise addition of longtime rival Sting, to combat Funk's J-Tex Corporation. This led to an "I Quit" match at *Clash of the Champions IX: New York Knockout* which Flair won. Flair then kicked Sting out of The Four Horsemen upon his challenge for the WCW World Heavyweight Championship, resulting in a revived feud between the two. On July 7, 1990, Flair dropped the title to Sting at The Great American Bash. After being unmasked as **The Black Scorpion** at Starrcade in 1990, Flair regained the title from Sting on January 11, 1991.

On March 21, 1991, Tatsumi Fujinami defeated Flair in a match in Tokyo at the WCW Japan Supershow. WCW did not officially recognize Fujinami's reign because Fujinami had backdropped Flair over the top rope in a violation of WCW rules. On May 19, 1991, Flair defeated Fujinami at SuperBrawl I in St. Petersburg, Florida to retain the WCW World Heavyweight Championship. In the spring of 1991, Flair had a contract dispute with WCW president Jim Herd. Two weeks before The Great American Bash, Herd fired him and vacated the WCW World Heavyweight Championship.

Flair signed with the World Wrestling Federation (WWF) in August 1991 and began appearing on television with the Big Gold Belt, calling himself "The Real World Champion". Led by his "financial adviser" Bobby Heenan and his "executive consultant" Mr. Perfect, Flair repeatedly issued challenges to WWF wrestlers like "Rowdy" Roddy Piper and Hulk Hogan, wrestling a team led by Piper at Survivor Series in November 1991 and helping The Undertaker defeat Hogan for the WWF Championship that same night.

At the 1992 Royal Rumble, Flair won the Rumble match to claim the vacant WWF Championship. Flair entered as number three in the Rumble match and lasted 60 minutes, last eliminating Sid Justice with help from Hulk Hogan, who had been eliminated by Justice seconds earlier. Randy Savage then challenged Flair for the WWF Championship 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, Miss Elizabeth. 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 in November 1992. Flair appeared in the Royal Rumble in January 1993, then lost a Loser Leaves the WWF match to Mr. Perfect on the next night's (January 25, 1993) *Monday Night Raw* in a match taped six days earlier. Flair then fulfilled his remaining house show commitments, making his last appearance on February 10, 1993, before returning to WCW.

Flair triumphantly returned to WCW as a hero in February 1993, as a result of a "no-compete" clause he was unable to wrestle, so he hosted a short-lived talk show in WCW called *A Flair for the Gold*. Arn Anderson usually appeared at the bar on the show's set, and Flair's maid Fifi cleaned or bore gifts. Once he returned to action, Flair briefly held the WCW World Heavyweight Championship for a tenth time after defeating Barry Windham at Beach Blast. At Fall Brawl, Flair lost the title, now rebranded the WCW International World Heavyweight Championship, to "Ravishing" Rick Rude. At Starrcade in 1993, Flair defeated Vader to win the WCW World Heavyweight title. In the spring of 1994, Flair began a tweener turn and started another feud with longtime rival Ricky Steamboat and challenged Steamboat to a match at Spring Stampede which ended in a no contest from a double pin, causing the title to be held up. Flair then defeated Steamboat in a rematch to reclaim the held-up title on an episode of *WCW Saturday Night*. Flair then challenged Col. Robert Parker to wrestle one of his men at Slamboree, which turned out to be Barry Windham, whom Flair defeated, afterwards he quietly turned heel and took Sherri Martel as his manager. He would also wrestle Lord Steven Regal in a five-match series under Marquess of Queensberry Rules, which aired on *WCW Worldwide* between April 30 and May 28, in which Flair won the series, with 2 wins, 1 loss, and 2 draws.

In June 1994 at *Clash of the Champions XXVII*, Flair defeated Sting in a unification match, merging the WCW International World Heavyweight Championship with the WCW World Heavyweight Championship, and solidifying his heel turn. After becoming the unified and undisputed WCW champion, Flair feuded with Hulk Hogan upon Hogan's arrival in WCW in June 1994, losing the WCW World Heavyweight Championship to him in July at Bash at the Beach. Flair continued to feud with Hogan and finally lost to Hogan in a steel cage retirement match at Halloween Havoc. Flair took a few months off afterwards before returning as a wrestler and part-time manager for Vader in 1995 (explained on-air by having Flair nag Hogan for months until Hogan and Savage both petitioned WCW management to let Flair come back).

On April 29, 1995, Flair wrestled Antonio Inoki in front of 190,000 spectators in Pyongyang, North Korea at the May Day Stadium in a losing effort. The event was broadcast on August 4, 1995 on pay-per-view under the title of Collision in Korea. In the fall of 1995, Flair began a short feud with Arn Anderson, which culminated in a tag match that saw Flair turning on Sting to reform the new Four Horsemen with Flair as the leader, Arn Anderson, Brian Pillman, and Chris Benoit as the members. With the new Four Horsemen, Flair won the WCW World Heavyweight Championship two more times before the nWo invasion storyline began in WCW, with the first one being in December 1995 at Starrcade, where Flair defeated Lex Luger and Sting by countout and then defeated Savage after all three Four Horsemen members ran to the ring and Arn Anderson knocked out Savage with brass knuckles, thus allowing Flair to pin Savage to win the match and the title. Afterwards Savage won the title back on *Nitro* after Starrcade, but Flair won the next match at SuperBrawl VI to regain the championship. During the feud, Savage's manager Miss Elizabeth turned against him and became Flair's valet. Together with Woman and Debra McMichael, they would escort Flair to his matches until Miss Elizabeth was taken by the nWo in the fall and eventually returned as Savage's valet when he joined the nWo in 1997. Flair lost the WCW World Heavyweight Championship eventually three months later to The Giant. The feud with Savage continued with The New Four Horseman joining the Dungeon of Doom to create an Alliance to end Hulkamania. Together the factions wrestled Hogan and Savage in a triple steel cage, End of Hulkamania match; losing to the reunited Mega Powers. Afterwards, Flair went on to win the WCW United States Heavyweight Championship and there were also changes in the Four Horseman in 1996, as Brian Pillman left WCW and Steve "Mongo" McMichael became the fourth member.

Once again as a top fan favorite, Flair played a major role in the New World Order (nWo) invasion storyline in late 1996 and throughout 1997. He and the other Horsemen often took the lead in the war against Scott Hall, Kevin Nash, and Hollywood Hulk Hogan, whom Flair immediately challenged for the WCW World Heavyweight Championship at the *Clash of the Champions XXXIII*, but won only by disqualification. In September 1996, Flair and Anderson teamed with their bitter rivals, Sting and Lex Luger, to lose to the nWo (Hogan, Kevin Nash, Scott Hall, and an impostor Sting) in the WarGames match at Fall Brawl when Luger submitted to the impostor Sting's Scorpion Deathlock.

In October 1996, two developments occurred that affected the Four Horsemen when Jeff Jarrett came over to WCW from the WWF, and expressed his desire to join the Horsemen as he immediately gained a fan in Ric Flair, much to the chagrin of the other Horsemen. Flair finally let Jarrett join the group in February 1997, but the others did not want him, and in July 1997 was ultimately kicked out of the group by Flair himself, who had enough of the instability Jarrett's presence caused the Horsemen. Flair also feuded with Roddy Piper, Syxx, and his old nemesis Curt Hennig in 1997, after Hennig was offered a spot in The Four Horsemen only to turn on Flair and The Four Horsemen at Fall Brawl in September 1997, in which Hennig punctuated the act by slamming the cage door onto Flair's head.

In April 1998, Flair disappeared from WCW television, due to no-showing a live episode of *Thunder* on April 16, 1998 in Tallahassee, Florida. After the situation was settled, Flair made a surprise return on September 14, 1998 to ceremoniously reform the Four Horsemen (along with Steve McMichael, Dean Malenko, and Chris Benoit). Flair feuded with Eric Bischoff for several months afterward. Flair repeatedly raked Eric Bischoff's eyes during this feud. This culminated in a match at Starrcade between Bischoff and Flair in December 1998, which Bischoff won after interference from Curt Hennig, a former member of the Four Horsemen. The following night in Baltimore on *Nitro*, Flair returned and threatened to leave WCW, demanding a match against Bischoff for the presidency of the company. The match was made, and despite the nWo interfering on Bischoff's behalf Flair won and was granted the position of president of WCW. This resulted in a match at SuperBrawl IX between Flair and Hollywood Hogan for the WCW Championship, which Flair lost after being betrayed by his own son David Flair.

In spite of his son's betrayal, Flair signed a rematch at Uncensored which was billed as a First Blood barbed wire steel cage Match against Hogan where Flair's presidency and Hogan's WCW World Heavyweight Championship were on the line. Despite being the first to bleed, Flair won the match by pinfall thanks to the bias of the referee Charles Robinson, who counted Hogan out.

As on-air WCW President, Flair began abusing his power much like Bischoff had, favoring villains over fan favorites and even awarding the WCW United States Heavyweight Championship (which was vacated by Scott Steiner due to injury) to his son David and resorting to whatever means necessary to keep him as United States Heavyweight Champion. Flair eventually formed a stable of followers which included Roddy Piper, Arn Anderson and the Jersey Triad to keep things in order. Flair's reign as president came to an end on the July 19 episode of *Nitro*, when he faced and lost to Sting for the position. During the course of the match, Sting had Flair in his Scorpion Death Lock, but with the referee knocked unconscious, no decision could be reached. A returning Eric Bischoff came to the ring and began ordering the timekeeper to ring the bell, which he eventually did, awarding the match and the presidency to Sting (who promptly gave it up upon receiving it).

Flair won his last world titles in his career by winning the WCW World Heavyweight Championship twice during 2000, the company's last full year of operation. When WCW was purchased by the WWF in March 2001, Flair was the leader of the villainous group called the Magnificent Seven. Flair lost the final match of *Nitro* to Sting, recreating the second match of *Nitro* in 1995.

After an eight-month hiatus from wrestling, Flair made a return to the WWF on November 19, 2001. Flair reappeared on *Raw* following the end of the "WCW/ECW 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 to a consortium (namely Flair) prior to purchasing World Championship Wrestling and Extreme Championship Wrestling. Flair's feud with Vince McMahon led them to a match at the Royal Rumble in January 2002 in a Street Fight, where Flair defeated McMahon. Flair also wrestled The Undertaker at WrestleMania X8 in March 2002 where Flair lost. The "co-owner" angle culminated in early 2002, when Flair controlled *Raw* and McMahon controlled *SmackDown!.*

On the May 13 episode of *Raw*, Flair challenged Hulk Hogan to a no disqualifications match for the WWE Undisputed Championship. Flair would later lose the contest before moving onto a rivalry with Stone Cold Steve Austin. At Judgment Day, Flair teamed with The Big Show in losing fashion as they faced Steve Austin in a two-on-one handicap tag team match. On the June 3 episode of *Raw*, the feud between Flair and Austin would escalate after Austin defeated Flair in a singles contest. After Steve Austin abruptly left the renamed WWE in June while in a program with Flair, a match was hotshotted between Flair and McMahon for sole ownership of WWE, which Flair lost after interference from Brock Lesnar on the June 10 edition of *Raw*.

Flair's rivalry with Lesnar would continue into the month of June with Lesnar picking up wins over Flair in a singles match on the July 1 episode of *Raw* and in a tag team contest on the July 15 episode of *Raw*. At King of the Ring, Flair defeated Eddie Guerrero in a singles match after Guerrero and Chris Benoit would interrupt Flair's speech regarding losing his position as WWF co-owner; afterwards, Guerrero would lock Flair in his own signature figure four leg lock with help from Benoit. Flair then became involved in a short lived rivalry with Chris Jericho, leading to Flair defeating Jericho at SummerSlam, resulting in Flair being granted a World Championship match against Triple H on the September 2 episode of *Raw*, which he lost. Later on that same night, Flair would team with Rob Van Dam as the duo were successful in defeating the team of Triple H and Chris Jericho. At Unforgiven, Flair was unsuccessful in capturing the Intercontinental Championship in a singles contest against Jericho.

In September 2002 at Unforgiven, Triple H defended the World Heavyweight Championship against Rob Van Dam. During the match, Flair came down to the ring and grabbed the sledgehammer from Triple H and teased hitting him before hitting Van Dam, allowing Triple H to get the win, turning him heel in the process and accompanied Triple H to the ring as his manager. Shortly after, Batista moved from *SmackDown!* to *Raw* and Flair also began accompanying him to the ring while continuing to second Triple H. In June 2003 at Bad Blood, Flair was able to defeat Shawn Michaels after Randy Orton struck Michaels with a chair.

At the height of Evolution's power, the group controlled all of the male-based championships of *Raw* after Armageddon. Batista teamed with Flair to win the World Tag Team Championship from the Dudley Boyz (Bubba Ray Dudley and D-Von Dudley) in a tag team turmoil match and Triple H regained the World Heavyweight Championship from Goldberg (in a triple threat match that also involved Kane), with the help of the other members. In January 2004 at the Royal Rumble, Flair and Batista successfully defended the World Tag Team Championship against the Dudley Boyz in a tables match, and World Heavyweight Champion Triple H fought Shawn Michaels to no contest in a Last Man Standing match, thus retaining the championship. Flair and Batista lost the World Tag Team Championship on the February 16 edition of *Raw* to Booker T and Rob Van Dam. At WrestleMania XX, Evolution defeated the Rock 'n' Sock Connection (The Rock and Mick Foley) in a 3-on-2 handicap match. The following week on *Raw* during the 2004 WWE draft lottery, Flair and Batista defeated Booker T and Rob Van Dam to win their second and final World Tag Team Championship. but they lost the titles to World Heavyweight Champion Chris Benoit and Edge on the April 19 episode of *Raw*.

At SummerSlam, Orton pinned Benoit to become the new World Heavyweight Champion. On the episode of *Raw* after Summerslam, Batista hoisted Orton on to his shoulders in what appeared to be a celebration, but following the thumbs down from Triple H, the group proceeded to attack Orton. At Unforgiven, Triple H beat Orton to regain the World Heavyweight Championship, with help from Flair, Batista, and Jonathan Coachman. Orton's feud with Evolution continued until Survivor Series where Triple H, Batista, Gene Snitsky, and Edge were defeated by Orton, Maven, Chris Jericho, and Chris Benoit in a Survivor Series match for control of *Raw* over the following month.

In the Elimination Chamber match at New Year's Revolution, Batista, Orton and Triple H were the last three remaining in the match. Orton eliminated Batista with a RKO and Triple H pinned Orton with Batista's help to win the title. Triple H suggested that Batista not enter the Royal Rumble match, wanting the group to focus on Triple H retaining the title. Batista declined, entered the Rumble at number 28 and won. Triple H tried to persuade Batista to challenge the WWE Champion John "Bradshaw" Layfield of *SmackDown!* rather than for his World Heavyweight Championship. This involved Triple H plotting a feud between JBL and Batista, showing JBL badmouthing Batista in an interview and staging an attack on Batista with a limousine designed to look like Layfield's. The scheme was unsuccessful and at the brand contract signing ceremony, Batista chose to remain on Raw, infuriating Triple H and thus quitting the faction. Batista defeated Triple H for the World Heavyweight Championship at WrestleMania 21.

After Vengeance, Triple H took time off, Flair turned face for the first time since 2002 before going on to win the Intercontinental Championship, and the group was dissolved. Triple H returned at the "Homecoming" episode of *Raw* on October 3, where he was to team with Flair in a tag team match against Carlito and Chris Masters. After winning that match, Triple H betrayed Flair and attacked him with a sledgehammer. Flair retained the Intercontinental Championship against Triple H at Taboo Tuesday in a steel cage match, which was voted as such by the fans. Flair later lost to Triple H in a Last Man Standing non-title match at Survivor Series which ended their feud.

At the end of 2005, Flair had a feud with Edge that culminated in a WWE Championship Tables, Ladder and Chairs match on *Raw* in early 2006, which Flair lost. On the February 20 episode of *Raw*, he lost the Intercontinental Championship to Shelton Benjamin, thus ending his reign at 155 days. Flair defeated Mick Foley at Vengeance in a two out of three falls match, then 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 episode of *Raw*, Flair and Piper lost the Tag Titles to Rated-RKO. 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 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 on the WrestleMania 23 pre-show, 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.

On the June 11 episode 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 a three-month hiatus, Flair returned to WWE programming on the November 26 episode 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 Randy 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. The day after, Flair wrestled at WrestleMania XXIV in Orlando, Florida, losing to Shawn Michaels.

On the March 31, 2008 episode 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 Flair a standing ovation. Flair made his first post retirement appearance on the June 16, 2008 episode 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 Jericho was stopped by Triple H.

The following year on February 9, Flair once again confronted 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 during the Judgment Day pay-per-view, coming to the aid of Batista, who was being attacked by Legacy (Randy Orton, Cody Rhodes and Ted DiBiase). On the June 1 episode of *Raw*, Flair challenged Orton in a parking lot brawl match, after an interference from the rest of Legacy, the fight ended with Flair was trapped inside a steel cage and was punted by Orton.

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 class of 2012 with The Four Horsemen. On December 17, 2012, Flair returned to WWE as a non-wrestling personality 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. Flair's return was interrupted by CM Punk and Paul Heyman, escalating into a confrontation that ended with him locking Heyman in the figure-four leglock. After clearing the ring, Flair was assaulted by The Shield, until Ryback and Team Hell No (Kane and Daniel Bryan) helped Flair fend off the group.

Flair appeared on the main roster sporadically throughout 2013, as The Miz's mentor. He also occasionally appeared on *NXT* in 2013 and 2014, accompanying his daughter Charlotte to the ring.

Flair appeared on the April 28, 2014, episode of *Raw*, alongside the reunited Evolution 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 July 14, John Cena symbolically handed over his World Heavyweight Championship belt to Flair, telling him to "take it" while promoting his match at Battleground. On the post-SummerSlam *Raw* in August 2015, Flair interrupted Jon Stewart, who had saved Flair's 16 world title record by preventing Cena's victory the previous night, telling him that the record would be broken eventually and he would rather it would be by someone who he respects.

Flair began making more frequent appearances with Charlotte after she won the Divas Championship. In January 2016, Flair and Charlotte began displaying villainous traits, with Flair often getting involved in Charlotte's Divas Championship and later WWE Women's Championship defenses. This lasted until the May 23, 2016 episode of Raw, when Charlotte turned on him. On the November 28, 2016 episode of Raw, Flair returned to congratulate the new Raw Women's Champion Sasha Banks, who had defeated Charlotte to win the title.

WWE celebrated Flair's 70th birthday on a special episode of *Raw* on February 25, 2019 in Atlanta, Georgia. During the closing moments, Flair did not come out to the ring. Batista then returned and mysteriously assaulted his former mentor. The actual "attack" was never seen, only Flair being dragged by Batista. However, at WrestleMania 35, Flair assisted Triple H in defeating Batista for the first time in his career, to keep his in-ring career going. Flair appeared on the July 22 *Raw Reunion* episode and raised a toast alongside Triple H, Hulk Hogan, Stone Cold Steve Austin and various other fellow wrestlers of his era.

During the summer of 2020, Flair came back to WWE programming, supporting Randy Orton for a few weeks until the August 10 episode of *Raw*, when Orton performed a punt kick on Flair's head.

On November 22, 2020, he made an appearance at Survivor Series during The Undertaker's retirement ceremony.

Flair appeared with numerous legends on *Raw Legends Night* on January 4, 2021. He also appeared at ringside in Charlotte's match with Asuka as they faced Lacey Evans and Peyton Royce. On the January 11 episode of *Raw*, Flair turned heel again by causing Charlotte to lose her match to Lacey Evans, aligning himself with Evans in the process. During the following weeks, Flair managed Evans, usually distracting his daughter Charlotte, including a participation in the women's Royal Rumble. On the February 15 episode of *Raw*, Evans' pregnancy was announced and incorporated into a storyline. Evans was scheduled to face Asuka for the Raw Women's Championship at Elimination Chamber, but the match was cancelled due to her pregnancy and the storyline with Flair was cancelled.