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Initially, the set consisted simply of a set of five thin walls meeting in a corner with a Scottish plaque on the center wall. The two walls on either side had posters of Piper in action and a chair or two. The colors of the walls were then patterned in Royal Stewartplaid. However, when that was destroyed (see Memorable Moments below) in the fall of 1986, it was rebuilt as an almost permanent set taking on a more Scottish flavor complete with a painted portrait of Piper on the back wall; Guests of this Pit came through an arched entrance way in the center of the set rather than from the side of the set previously.
Piper's Pit returned during Piper's short return to the WWE in 2003. The segment also made a return in 2005 at WrestleMania 21 interviewing Stone Cold Steve Austin, the night after Rowdy Roddy Piper was inducted into the WWE Hall of Fame. Between then and Piper's 2015 death, the Piper's Pit segment has continued to make occasional appearances.
Since 2003, WWE programming has contained other Piper's Pit-style interview segments hosted by other WWE superstars. Examples of wrestlers who have hosted their own segments include Chris Jericho, Edge, Christian, Carlito, Santino Marella, Montel Vontavious Porter and René Duprée.
- For those who consider it important for a historical record, "Mr. Wonderful" Paul Orndorff was Piper's first guest; Orndorff talked about challenging then-new WWF champion Hulk Hogan for the title.
- Piper interviews André the Giant, and claims it is amazing that Andre has a "big body and a tiny, weeny brain," and asks Andre if Big John Studd has slammed him before, and after Andre says "never" and makes it clear to Piper that he can never be slammed. Piper then says "If I'm given five minutes, I could slam you myself," to which Andre responds by picking him up by the front of his shirt and throws him of the set before leaving. After André leaves the set, Piper responds and says "André, do you want to fight? You do not throw rocks at a man who's got a machine gun."
- Piper interviews jobber Frankie Williams, tells him that he's worthless and beats him up. This is where Piper coins one of his famous quotes: "Just when they think they've got the answers, I change the questions."
- On what was arguably the most famous episode of Piper's Pit, Piper interviewed Jimmy Snuka. During the episode, Piper tried to make Snuka "feel at home." After Snuka accused Piper of insulting him, Piper smashed a coconut shell over Jimmy Snuka's head. After that, he proceeded to throw him around and shove a banana down his throat before leaving through a back door, escaping a furious Snuka. (The segment itself was taped March 28, 1984, for airing in local St. Louis markets that weekend, to help build up the planned Piper-Snuka series of matches at the Kiel Auditorium in May; the segment did nor air nationally until the weekend of June 9, 1984, after which the feud was expanded.)
- Special guest '80s pop star Cyndi Lauper attacks Capt. Lou Albano and Piper himself after hearing enough insults from Albano. Lauper made numerous appearances on the Pit during late 1984, playing off her association with Albano (which off-screen they were working together to raise funds for multiple schleorsis research).
- In a Pit emanating from Madison Square Garden, Piper played mind games with his guest Mr. T, showing some rather humorous cartoons of what the star of the A-Team may look like after their main event at WrestleMania, and takes it to higher levels by wearing a Mr. T cap and mocking Mr. T's mohawk hairstyle.
- On a special Pit on the May 11, 1985 edition of Saturday Night's Main Event, Piper berates and betrays "Mr. Wonderful" Paul Orndorff in the wake of their recent loss to Mr. T and Hulk Hogan in the main event at the first WrestleMania. Piper then tries to jump Orndorff, but is beat to the punch. Orndorff goes off on both Piper and bodyguard "Cowboy" Bob Orton, then attempts to piledrive Piper but is blindsided by Orton and his cast from behind.
- For home video only, Piper is on the set interviewing his all-time favorite guest, himself, using the merged-screen technique.
- In late 1985, Piper invites Bruno Sammartino onto his show at Madison Square Garden to insult him. Sammartino refuses to participate in the interview until Orton agrees to leave the ring. Piper and Orton eventually attack Sammartino, but the "Living Legend" gets the upper hand.
- In early 1986, Piper interviews George "the Animal" Steele and Captain Lou Albano regarding Steele's feud with Randy "Macho Man" Savage and crush on Miss Elizabeth. After Orton implies that Elizabeth has offensive body odor (causing Steele to momentarily run Orton off the set), Piper questions Steele about his infatuation for Elizabeth and calling him an imbicile; Steele cleverly grabs Piper's kilt, points at his leg and says, "'Lizabeth!" prompting Piper and Orton to walk off the set.
- Two "Pit" segments during February 1986 were used to build up Piper's boxing match against Mr. T at WrestleMania 2. First, Piper's arch-enemy Hogan appeared to accept Piper's open challenge for the match on Mr. T's behalf; Piper snickered at the thought of easily beating Hogan until he read the fine print, which caused him to gasp in disbelief. Weeks later, Piper and Orton beat down the Haiti Kid, bring him onto the Pit set and shave Haiti Kid's hair into a Mr. T-style mohawk; after they were finished, Piper makes the illogical comment, "If we can do this to you, can you imagine what I'm going to do to Mr. T?"
- Adrian Adonis changes gimmicks on the spot, foregoing his leather jacket that embodied his bad-boy biker persona for the more flamboyant, borderline homosexual gimmick that he would take on for the remainder of his World Wrestling Federation tenure.
- A newly turned face Piper, while engaged in a violent feud with "Adorable" Adrian Adonis, is brutally attacked and knocked unconscious during the infamous "Flower Shop vs. Piper's Pit" showdown by Adonis and former Piper allies Bob Orton, Jr. and Don Muraco, who then proceed to destroy the set. A crippled yet enraged Piper would gain revenge by destroying Adonis' "Flower Shop" set a week later. (While Piper's Pit would be quickly rebuilt better than ever, the Flower Shop never returned.)
- Uninvited guest Jimmy Hart insults and distracts Piper as Adonis comes out of nowhere to make a surprising return from a previous Piper attack to ambush the Rowdy One, causing a brawl on the set. With Hart's help, Adonis would eventually get the better of Piper, rendering him unconscious with "The Goodnight Irene" sleeper hold. To add insult to injury, he put a flower in Piper's mouth before he and Hart walked off-set.
- André the Giant turns heel on Hulk Hogan, comes onto the set with Bobby Heenan, and challenges him to a match at WrestleMania III, and rips off his shirt and crucifix before walking off the set with Heenan as well. Piper shocked many fans by actually comforting Hogan and leading him offstage. About a week later, Hogan returned to the pit to give his answer to whether or not he'll take Andre's challenge; "YEEEEEEEEEEESSS!"
- In a highly-emotional Pit, Piper announced his "retirement" because he couldn't bear to hear his children begging him to stay home. He stood on a table to get a better look at the cheering fans, thanked them for supporting him, then took the photo and painting of himself off the back wall of the set and quietly left.
- At WrestleMania V, Roddy shot Morton Downey, Jr. with a fire extinguisher to counter Morton blowing second hand smoke in his face.
- Piper and Sean O' Haire invite a fan from the audience in the ring who was a fan of Mr. America then proceeded to attack him, which lead to his artificial leg being ripped off, thus introducing the world to Zach Gowen
- The Boogeyman chews off the mole on Jillian Hall's face during a segment in the Pit where Piper was interviewing Hall's client, John "Bradshaw" Layfield.
- The Pit makes a return to WrestleMania in 2005 with Stone Cold Steve Austin. This is the first time the Pit appeared at the pay-per-view show since WrestleMania V.
- Shawn Michaels superkicked Piper on the set of the pit a week after he attacked Hulk Hogan following a tag team match.
- Jimmy Kimmel's cousin Sal was taught how to wrestle by Piper in a match against Santino Marella.
- Chris Jericho impersonates Piper and assaults Jimmy Snuka.
- Piper interviews actor Luis Guzman along with a confused Iron Sheik in Madison Square Garden.
- Rusev and Lana appeared on ‘Piper’s Pit’ on December 22, 2014.