Around this time World Wrestling Federation (WWF) owner Vince McMahon contacted Piper, who insisted on serving out his contract with Jim Crockett. Piper started in the WWF in late 1983 and at the same time fulfilled dates with Crockett. On his way out of Crockett's promotion he became a heel, which set the stage for his WWF run in 1984. He started as a manager at first, due to the injuries he sustained during his dog collar match with Greg Valentine, but soon started wrestling full-time. Piper came in as the manager for "Mr. Wonderful" Paul Orndorff, and soon began to wrestle with Orndorff as well.
Later that year, he was given his own interview segment called Piper's Pit, in which he talked to other superstars and which frequently ended in a fight between Piper and his guest. The Piper's Pit segments helped create the feuds Piper had with other wrestlers. According to Piper's autobiography, Piper's Pit was completely unscripted and was in fact so popular that it was taken on the road. In addition to pleasing many of his fans who wanted to see the Pit in person, it accomplished other things: it gave Piper the opportunity to heal some nagging injuries while still retaining his heat with the fans. An early guest on Piper's Pit was his Mid-Atlantic nemesis Valentine, who also arrived to the WWF. In a rare occurrence for WWF programming at the time, the two made reference to their history in the rival organization and hinted at rekindling it, but as the two were now top villains, they both agreed that they had mutual respect for each other, and it was left at that. In one Piper's Pit, Piper had an interview with Jimmy Snuka. Piper started insulting Snuka's Polynesian heritage by bringing out pineapples, bananas, and dropping coconuts onto the table; this was to make Snuka "feel at home" in an act of "remorse" after Snuka was not given much time to speak the previous times he was on Piper's Pit. Snuka took offense to this and Piper then attacked Snuka by smashing him over the head with a coconut and shoving a banana in his face. He followed this up by whipping Snuka with his belt. Snuka was legitimately knocked woozy allowing Piper to leave before Snuka, now seriously enraged, could fight back. This incident led to a long feud between the two. Piper also insulted Bruno Sammartino during a Piper's Pit which led to a feud between the two, ending in a steel cage match which Piper lost.
Another feud, this time between Piper and Hulk Hogan erupted soon after and became what was at the time the highest-profile feud in wrestling history, thanks to the involvement of pop singer Cyndi Lauper, where Piper kicked Lauper in the head—and even attacked Captain Lou Albano—with Hogan seeking revenge as a result. In 1985, MTV broadcast The War to Settle the Score, featuring a main-event matchup between Piper and Hogan, who was accompanied to the ring by Albano, Lauper, and Mr. T. This event set up the very first WrestleMania, which pitted Piper and Paul Orndorff against Hogan and Mr. T. Orndorff was pinned by Hogan when Piper's bodyguard "Cowboy" Bob Orton interfered and mistakenly struck Orndorff instead of Hogan with his trademark "injured" arm covered in a plaster cast. In Born to Controversy, Piper recalled how he had to keep Mr. T busy with tie-ups and other shoot wrestling moves to keep Mr. T's lack of wrestling ability from being seen by the fans, thus ruining the match. From this situation, Piper and Mr. T's real-life relationship became hostile, leading to the inevitable conclusion that they be put into a feud with one another. Piper once again faced Mr. T, this time alone, in a boxing match at WrestleMania 2 in 1986. Piper lost the match by disqualification after bodyslamming Mr. T.
Following a leave of absence from the WWF, Piper returned during a TV taping on WWF Superstars in 1986 against jobber A.J. Petruzzi and seemed to be a fan favorite. After being slapped in the face by Bertuzzi twice, Piper placed one hand behind his back and beat his opponent to a pulp. In another Piper's Pit, which happened not long before WrestleMania III, Jesse Ventura dared Piper to have André the Giant and Hulk Hogan interview each other, which they did. Andre, who was accompanied by Bobby Heenan, his manager at the time, challenged Hogan to a championship match at WrestleMania. Hogan, trying to avoid actual physical contact, tried to calm Andre down, but Heenan ordered him to push Hogan to the ground, which he did, before leaving. The segment ended when Piper asked if Hogan still wanted to challenge Andre at WrestleMania, and Hogan replied yes.
Piper was distressed to find his Piper's Pit segment replaced by The Flower Shop, a segment hosted by the then effeminate wrestler Adrian Adonis. Piper spent weeks crashing Adonis' show and trading insults, leading to a "showdown" between the two segments that ended with Piper being assaulted and humiliated by Adonis, Piper's former bodyguard Orton (now in Adonis' employ), and Don Muraco. The trio left Piper with his face covered in red lipstick lying in the middle of the remnants of the Piper's Pit set, which had been destroyed. In response, Piper stormed the set of Adonis' show and destroyed it with a baseball bat. This led to their Hair vs Hair match at WrestleMania III, which was billed as Piper's retirement match from wrestling before he left to become an actor full-time. Piper won the match with the assistance of Brutus "The Barber" Beefcake, who had been sheared by Adonis shortly before the match.
Piper returned from a hiatus with a live Piper's Pit at WrestleMania V, where he hosed down a smoking Morton Downey, Jr. with a fire extinguisher. He also wrestled part-time, while serving as an on-air host and commentator, at that time feuding with "Ravishing" Rick Rude after playing a part in Rude losing his Intercontinental Title at SummerSlam in August 1989. Piper also wrestled Bad News Brown at WrestleMania VI in 1990. The match ended with both men being counted out of the ring, but the real highlight of the match was Piper's choice of ring attire. In true 'Rowdy' fashion, Piper cut a promo and came to the ring with half his body painted black in a strange attempt to play head games with Bad News.
In 1991, he supported Virgil in his feud against Ted DiBiase and was present at their matches at WrestleMania VII and SummerSlam. He also renewed his feud with Ric Flair and at the 1992 Royal Rumble defeated The Mountie for his first, and only, Intercontinental Championship. He lost it soon after to Bret Hart at WrestleMania VIII. After playing the bagpipes at SummerSlam, he disappeared from the WWF.
He reemerged in 1994 at WrestleMania X as guest referee for the WWF Championship match between Bret Hart and Yokozuna. During the match, commentator Jerry Lawler remarked that he hated Piper and continued to taunt Piper on his King's Court segment on Monday Night Raw, eventually culminating with Lawler bringing out a skinny teenager in a Piper T-shirt and kilt and forcing him to kiss his feet. Enraged, Piper agreed to wrestle Lawler at the King of the Ring, where Piper emerged victorious. Piper wrestled as a fan favorite, saying he had "made a mess of most of his career as a heel", and adding to the face attitude by donating part of his purse from the fight with Lawler to a children's hospital in Ontario.
Leaving the WWF again, he soon returned in 1995 at WrestleMania XI, once again in a referee capacity, for the submission-only match between Hart and Bob Backlund. In 1996, Piper was named as interim WWF President, following Vader's malicious assault on Gorilla Monsoon, following the Royal Rumble. As president, Piper had become the object of affection for Goldust. Enraged, Piper claimed he would "make a man" out of Goldust at WrestleMania XII, in a "Hollywood Backlot Brawl." While the contest began in an alleyway behind the Arrowhead Pond, Goldust jumped into his gold Cadillac and ran Piper over, ultimately escaping (allegedly) onto the highways of Anaheim. Piper pursued in his white Ford Bronco, which when viewed from aerial footage looked similar to the O. J. Simpson "low-speed" chase from two years prior (the WWF had attempted to be humorous and recycle the footage with Vince McMahon quipping on commentary, "This footage looks awfully familiar"). The two eventually returned to the arena, where Piper disrobed Goldust in the ring, effectively ending the confrontation. With Gorilla Monsoon back in control of the WWF by the end of the night, Piper once again left the Federation.
Later in 1996, Piper joined World Championship Wrestling (WCW). He appeared at Halloween Havoc to "break Hogan's monotony." In his first appearance, Piper asked Hogan, "Do you think [the fans] would've loved you so much, if they hadn't hated me?" Piper and Hogan wrestled in a non-title match in the main event of Starrcade, WCW's biggest pay-per-view event of the year. Piper defeated Hogan with a sleeper hold. Piper faced Hogan in a title match at SuperBrawl VII. This time, Hogan beat Piper when Randy Savage interfered and joined the New World Order (nWo). Promos showed Piper locking himself in the Alcatraz prison and vigorously exercising in order to prepare for the highly anticipated match. During the spring of 1997, Piper joined forces with Ric Flair and The Four Horsemen in their battle with the nWo. Shortly thereafter, Piper and Flair feuded before Piper disappeared from the scene. Piper briefly returned in October 1997 to face Hogan once again in a steel cage match.
In early 1998, Piper once again returned to feud with Hulk Hogan, Randy Savage, and Bret Hart. In early 1999, Piper had a short run as United States Champion, became WCW Commissioner, and resumed his feud with Flair over control of WCW. Piper also had a short feud with Buff Bagwell in the summer of 1999, where he was defeated by Bagwell, whose mother got involved. In late 1999, Piper was featured on WCW Television, in an angle with Vince Russo, who was now portraying himself as the "Powers That Be" (an unseen power that was controlling WCW). At Starrcade, Piper was the special referee in the WCW title match featuring Goldberg and Bret Hart. Forced by Russo, Piper called for the bell when Hart locked in the Sharpshooter on Goldberg, when it was apparent that Goldberg had not submitted. Piper apologized for this incident the next night on Nitro and attempted to make the save for Goldberg when Bret Hart and the nWo beat him down, but the nWo also attacked Piper. Piper's last appearance was at SuperBrawl in 2000 where he was a surprise referee in the title match between Sid Eudy and Jeff Jarrett. The feud between Piper and the Powers That Be ended shortly after and Piper disappeared, never to be seen on WCW TV again. In the fall of 2000, WCW terminated Piper's contract, and the organization ceased to exist after being sold to WWF several months later.
In November 2002, Piper's autobiography, In the Pit with Piper: Roddy Gets Rowdy, was released. At WrestleMania XIX in Seattle, Washington, Piper ran in during the Hulk Hogan-Vince McMahon match and made his second WWE run as a villain by attacking Hogan with a steel pipe. He brought back Piper's Pit on the April 10 edition of SmackDown!, and after aligning with Sean O'Haire, Piper smashed a coconut over the head of Rikishi, a relative of Snuka. At Backlash that month, Rikishi returned the favor to Piper. Piper was then put in a program against "Mr. America". The storyline was Hulk Hogan had been bought off WWE television forever by McMahon. Hulk Hogan returned "incognito" although the joke was that everybody knew who he really was, which infuriated McMahon. At this point, Piper and O'Haire were portrayed as McMahon's lackeys attempting to unmask Mr. America. Despite Piper being a heel he still got cheered due to being a legend.
Around the same time on Raw, Chris Jericho started The Highlight Reel—a show similar to Piper's Pit. The two even verbally sparred on TV, with Jericho calling Piper fat and telling him to call him "when he lost some weight"; Piper's retorted, "I have seen Chris Jericho wrestle. I have heard Chris Jericho talk. I have even heard Chris Jericho sing. So I'll make you a deal: I promise you that when I lose some weight, I'll call you. And when you get some talent, you call me." At Judgment Day, the two met again, with Jericho telling Piper he made a wrong turn and missed the senior's home and alluding to the incident where Piper ripped off a fan's (later revealed to be Zach Gowen) leg and used it as a weapon, mentioning there were some midgets and lepers he could thrash, and while patting Piper's stomach, asked if he ate the leg. Piper responded by blasting him for ripping off the Piper's Pit idea and drilling it into the ground and called Jericho's birth an "accident". In June 2003, WWE decided to stop using Piper (who was working without a contract at the time) after a controversial interview with HBO's Real Sports with Bryant Gumbel in which Piper discussed the darker side of the wrestling business. On his 2006 DVD, Piper claimed that HBO took parts of his interviews out of context to make wrestling look worse.
On February 21, 2005, it was announced that Piper was to be inducted into the WWE Hall of Fame. Piper held an edition of Piper's Pit at WrestleMania 21 where he interviewed Stone Cold Steve Austin. The interview was interrupted by Carlito, who was promptly beaten up by both Piper and Austin.
On the July 11, 2005 episode of Raw, Piper returned as a face to host Piper's Pit with guest Shawn Michaels, who superkicked Piper at the end of the show. This was during Michaels' feud with Hulk Hogan. Piper once again appeared on Raw on October 3, 2005 for Raw Homecoming. He hosted Piper's Pit with guest Mick Foley; later in the segment, Randy Orton and "Cowboy" Bob Orton appeared and attacked both Foley and Piper. This event sparked a mini-feud between Piper and The Ortons. On the next SmackDown! after Homecoming, Piper took on the Ortons in a handicap match. Piper won with a roll-up on Bob Orton after a distraction by The Undertaker. On October 28, Piper teamed with Batista and Eddie Guerrero to take on Randy Orton, Bob Orton, and Mr. Kennedy. Piper won after applying the sleeper hold to Bob Orton. Piper's feud with The Ortons came to an end on the November 4, 2005 episode of SmackDown! with a DQ victory over Bob Orton.
Piper returned to Raw on September 11, 2006 for a six-man tag team match win with The Highlanders against the Spirit Squad. He also appeared on the Raw Family Reunion, along with Money Inc. and Arn Anderson to accompany Ric Flair ringside for a match against Mitch of the Spirit Squad. On November 5, Piper won the World Tag Team Championship with Ric Flair from The Spirit Squad at Cyber Sunday, after being chosen to be Flair's partner by voters at WWE.com over Sgt. Slaughter and Dusty Rhodes. On the November 13, 2006 edition of Raw, Piper and Flair lost the title to Rated-RKO. Piper never made it to the ring, as he was attacked by Edge with a con-chair-to before the match. On November 17, 2006, WWE announced on their website that Piper was flown from the UK to his home state of Oregon and had surgery for what was originally believed to be kidney stones, but was speculated to be a disc problem in his back. It was later determined to be cancer. As a result of the procedure, it was announced that he was withdrawing from the Survivor Series match which would have pitted himself (as a co-captain), along with Flair, Anderson, Sgt. Slaughter, and Dusty Rhodes against the Spirit Squad. He was replaced with Ron Simmons.
He made a return to Raw on an episode taped February 12, 2007, during which he announced that his friend Dusty Rhodes was to be the first person inducted into the 2007 class of the WWE Hall of Fame. During his appearance Umaga, with manager Armando Alejandro Estrada, entered the ring and laid out both men. He then returned on the June 11, 2007 edition of Raw as part of "Mr. McMahon Appreciation Night", where he introduced a video of some of McMahon's most embarrassing moments. In 2008, after finishing his therapy for Hodgkin's lymphoma, he made a brief appearance in the Royal Rumble, primarily focusing on "Superfly" Jimmy Snuka. Both men were eliminated by Kane shortly after they entered the ring.
Piper returned to Raw on April 28, 2008. He was a backstage visitor, and was confronted by Santino Marella. Marella poked fun at Piper's weight, which resulted in Santino getting slapped by Piper. The next week, Piper was a guest on Carlito's Cabana and Carlito and Santino were about to double team Piper when they were chased off by Cody Rhodes and Cryme Tyme. On May 12, Piper's interference stopped Santino and Carlito from beating Rhodes and Hardcore Holly for the World Tag Team Championship. Santino then threatened Piper with retaliation, culminating in a confrontation with Piper during the May 16 edition of Jimmy Kimmel Live!. He wrestled his presumed last match on April 18, 2008 one day after his 54th birthday at Newburgh Free Academy’s Spring Slam.
On October 26, 2008, however, Piper appeared on WWE's Cyber Sunday as one of the three choices fans could choose to face Marella for the WWE Intercontinental Championship. The other choices were Goldust and The Honky Tonk Man. Honky Tonk Man was chosen and won via a disqualification due to interference by Beth Phoenix and therefore did not win the title. Goldust then entered the ring, followed by Piper. The three candidates then fought Santino, afterwards celebrating together in the ring. Piper appeared on the October 27, edition of Raw as a special guest commentator, along with both Goldust and Honky Tonk Man, for Marella's match against Charlie Haas.
On February 16, 2009 Piper returned to Raw to confront Chris Jericho after Jericho continued to act disrespectfully towards the Hall of Famers. After the segment, Jericho attacked Piper.
One month later, on the March 16 edition of Raw, Piper would get his revenge when he, along with Ric Flair, Jimmy Snuka, and Ricky Steamboat, attacked Jericho.
For the first time in several years, Piper wrestled at WrestleMania XXV along with Snuka and Steamboat with Flair in their corner to go against Jericho in a three on one handicap match. Jericho won the match; Piper was the second of the three to be eliminated.
Piper guest hosted WWE Raw on November 16, 2009 at Madison Square Garden in New York City. Piper challenged Vince McMahon to a street fight later in the evening only to have Randy Orton come out to fight against, then shortly after Kofi Kingston came out to stop Randy's assault on Piper.