Before "Stone Cold" became Stone Cold, before the Attitude Era shocked television audiences, one man blazed the trail by shattering wrestling’s fourth wall. The transformation of Brian Pillman from high-flying technician to unhinged "Loose Cannon" didn’t just push boundaries – it obliterated them. These thirteen watershed moments, including a controversial incident involving Bobby Heenan, reveal how a single performer revolutionized professional wrestling forever.
1. The Brutal WrestleWar Cage Match Surrender (February 24, 1991)
Sid Vicious after delivering a devastating cage-top powerbomb to Brian Pillman at WCW WrestleWar 1991. Photo Credit: WWE.
The WarGames match at WCW WrestleWar took place on February 24th, 1991, at the Arizona Veterans Memorial Coliseum in Phoenix, drawing 6,800 fans. The Four Horsemen (then Barry Windham, Larry Zbyszko, Ric Flair, and Sid Vicious) faced Brian Pillman, Sting, Rick Steiner, and Scott Steiner in the main event. Zbyszko served as a replacement for an injured Arn Anderson.
The match reached its climactic moment when Sid Vicious isolated Pillman in the ring. Vicious executed two powerbombs on Pillman, with the second one particularly dangerous as the cage’s low ceiling caused Pillman’s head to make contact with the roof. After the impact, El Gigante appeared at ringside and threw in the towel on Pillman’s behalf at 21:50, giving the victory to the Four Horsemen.
This WarGames match became notorious in wrestling history for its finish, which saw Pillman rendered unable to continue after the powerbomb sequence. The bout’s conclusion led to immediate concern for Pillman’s safety and marked a significant moment in both performers’ careers.
Years later, Sid Vicious admitted in interviews that the dangerous powerbomb spot was intentionally executed due to backstage tensions between the two performers. The incident sparked a legitimate feud that would later culminate in the infamous "Squeegee Incident" at an Atlanta hotel bar.
Dave Meltzer awarded the match five stars in the Wrestling Observer Newsletter, noting it as one of the best WarGames matches he’d ever seen live. The bout received a 97.3% approval rating from fans, making it the third-highest-rated match in Observer poll history at that time.
2. Making History as the First WCW Light Heavyweight Champion (October 27, 1991)
Brian Pillman after being crowned the inaugural WCW Light Heavyweight Champion on October 27th, 1991. Photo Credit: WWE.
On October 27th, 1991, at the UTC Arena in Chattanooga, Tennessee, Brian Pillman captured the inaugural WCW Light Heavyweight Championship by defeating Richard Morton in the tournament finals. The match, which lasted 12 minutes and 43 seconds, concluded when Pillman executed his signature crossbody from the top rope for the victory.
The tournament began in August 1991 with eight competitors. Pillman advanced to the finals by defeating Badstreet (Brad Armstrong) at Clash of the Champions XVI on September 5th, while Morton earned his spot by defeating Mike Graham on the same night through heel tactics, using the ropes for leverage.
The historic championship match featured an innovative element – referee Nick Patrick wore a "Refer-Eye" video camera helmet to capture unique angles of the action.
Pillman’s first reign lasted 59 days before losing the title to Jushin "Thunder" Liger on December 25th, 1991, at a house show in Atlanta. He would regain the championship from Liger at SuperBrawl II on February 29th, 1992, becoming the only wrestler to hold the title multiple times during its brief existence.
The Light Heavyweight Championship represented WCW’s early attempts to showcase a more athletic style of wrestling that would later define the company’s cruiserweight division. Pillman’s matches during this period, particularly with Liger, helped establish the framework for WCW’s acclaimed junior heavyweight style of the mid-1990s.
3. Hollywood Blonds Capture WCW Tag Team Gold (March 27, 1993)
The Hollywood Blonds (Steve Austin and Brian Pillman) showing off their belts after their historic tag team championship victory on WCW Power Hour, March 1993. Photo Credit: WWE.
Initially thrown together as a random pairing, Brian Pillman and “Stunning” Steve Austin formed the Hollywood Blonds, taking their name from the legendary 1970s tag team of Buddy Roberts and Jerry Brown. The duo quickly developed chemistry, with Pillman suggesting they wear matching ring gear to solidify their team identity.
On March 27th, 1993, the Hollywood Blonds defeated Ricky Steamboat and Shane Douglas on WCW Power Hour to capture the NWA/WCW World Tag Team Championship. Their signature taunt involved miming an old film camera after successful moves, followed by their catchphrase “Your brush with greatness is over.”
The team’s success was short-lived but impactful. Despite growing popularity with fans, backstage politics led to their premature split. After Pillman suffered an ankle injury, WCW substituted Lord Steven Regal in his place for a title loss to Arn Anderson and Paul Roma at Clash of Champions XXIV. The Hollywood Blonds officially disbanded on October 30th, 1993.
4. Thunder in the Cage at SuperBrawl (February 20, 1994)
Brian Pillman teams with Sting and Dusty Rhodes against Paul Orndorff, Rick Rude, and Steve Austin in a ThunderCage at WCW SuperBrawl IV, February 20th, 1994. Photo Credit: WWE.
On February 20th, 1994, at the Albany Civic Center, Brian Pillman teamed with Sting and Dustin Rhodes to face Steve Austin, Rick Rude, and Paul Orndorff in WCW’s signature ThunderCage match. The 14-minute and 36-second bout marked a significant chapter in the ongoing rivalry between former Hollywood Blonds partners Pillman and Austin.
The match showcased intense physicality, with Pillman taking a brutal cage bump that left him bleeding after Austin and Orndorff repeatedly threw him into the steel structure. Despite the punishment, Pillman executed a perfectly timed dropkick on Austin as his former partner came off the top rope.
The bout’s climax came when Sting press-slammed Pillman onto Austin in a spot reminiscent of the British Bulldogs’ finishing move, securing the victory for the babyface team. Dave Meltzer of the Wrestling Observer Newsletter rated the match ★★★¼, praising its energy and calling it the best match of the evening.
The aftermath saw Rick Rude slam Sting’s head into the cage door and deliver the Rude Awakening on the floor, setting up their continued feud. The match stood as one of the final high-profile encounters between Pillman and Austin before both men would revolutionize the industry in different promotions.
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5. The Four Horsemen’s Mall of America Deception (September 4, 1995)
Brian Pillman joins the revamped Four Horsemen with Ric Flair, Chris Benoit, and Arn Anderson, September 1995. Photo Credit: WWE.
On September 4th, 1995, WCW made history with the debut episode of Monday Nitro from the Mall of America in Minneapolis. Brian Pillman opened the show by defeating Jushin "Thunder" Liger in a rematch from their acclaimed SuperBrawl II encounter.
The episode marked the beginning of a calculated deception. After Arn Anderson cost Ric Flair his match against Sting at Fall Brawl, Anderson and Pillman declared themselves the "New Horsemen," vowing to end Flair’s career. This led to Flair recruiting Sting as his partner against the duo at Halloween Havoc.
The ruse reached its climax at Halloween Havoc when Sting found himself alone against Anderson and Pillman. When Sting needed help, Flair emerged with his head bandaged, tagged in, and immediately turned on his partner. The bandage removal revealed the entire scenario had been orchestrated between Flair, Anderson, and Pillman.
This reformation of the Four Horsemen added Chris Benoit in November 1995, creating what many considered the most technically skilled version of the group. The new lineup featured Flair as the leader, Anderson as the enforcer, Pillman as the wild card, and Benoit as the intense competitor who would eventually replace Pillman after his departure in early 1996.
The Mall of America deception demonstrated the Four Horsemen’s mastery of long-term storytelling, with the angle playing out over several months across multiple pay-per-views and episodes of Nitro. The storyline helped establish Monday Nitro as direct competition to WWF’s Monday Night Raw, drawing a 2.5 rating for its debut episode.
6. Birth of the Loose Cannon (Late 1995)
Brian Pillman debuted his revolutionary "Loose Cannon" persona in late 1995. Photo Credit: WWE.
In late 1995, Brian Pillman joined a reformed Four Horsemen alongside Ric Flair, Arn Anderson, and Chris Benoit. During this period, he began displaying increasingly erratic behavior both on-screen and backstage, developing what would become known as the “Loose Cannon” persona.
Pillman transformed his clean-cut “Flyin’ Brian” image into something entirely different. He adopted a new look featuring leather vests, sunglasses, and graphic t-shirts adorned with skulls and provocative imagery. His promos became more intense and unpredictable, frequently deviating from scripts and blurring the lines between performance and reality.
The character was so convincing that even close friends like Jim Ross, Mick Foley, and Steve Austin were unsure whether Pillman was working or legitimately unstable. Jim Ross later revealed that when he finally asked Pillman about the character, Pillman initially left him hanging before eventually letting him in on the carefully crafted deception.
The genius of Pillman’s “Loose Cannon” lay in its authenticity. In an era when WCW programming largely featured cartoonish characters, Pillman’s unpredictable persona became the most compelling part of the product. His commitment to maintaining kayfabe was so complete that he kept even his closest colleagues guessing, making his character one of the best-kept secrets in wrestling history.
7. The Bobby Heenan Incident (January 23, 1996)
Brian Pillman confronts Bobby Heenan during an unscripted incident at WCW Clash of Champions on January 23rd, 1996. Photo Credit: WWE.
During a match with Eddie Guerrero at WCW Clash of Champions XXXII on January 23rd, 1996, Brian Pillman’s "Loose Cannon" character took an unscripted turn. After rolling to ringside and taunting fans, Pillman approached the commentary table and grabbed Bobby Heenan’s jacket.
Heenan, who had suffered severe neck injuries from a match in Japan years earlier, had a strict no-contact clause in his WCW contract. Unaware of these restrictions, Pillman’s actions caused Heenan to react with genuine fear, shouting an expletive live on air (“What the **** are you doing?”) before storming away from the announce position.
The incident’s impact lasted throughout the broadcast. Eric Bischoff later revealed that for the remainder of the night, Heenan would grab his jacket and leave the announce table whenever wrestlers came near. Though Pillman later apologized backstage, the moment became a defining example of how his "Loose Cannon" persona blurred the lines between performance and reality.
“This incident preceded Pillman’s infamous "I respect you, Bookerman" moment with Kevin Sullivan and his eventual departure from WCW.
Years later, Heenan provided more context about the incident. “I’m watching the monitor,” Heenan shared, “and I didn’t know Pillman, never met him. He walked behind me and put my coat down around my shoulders just playing, right? But I had had neck damage.”
“I thought it was a fan at first who attacked me,” Heenan recalled, “but I didn’t know it was Pillman.” He expressed frustration with wrestlers’ tendency to interfere with commentators: “Wrestlers are dumb; they think go mess with the announcers because they’re on camera all the time. Don’t they ever watch the show? We’re only on camera maybe at the beginning, maybe at the end.”
Heenan also criticized WCW’s production values and leadership during this period: “It was a television production that had nobody in charge that knew what they were doing. It was pitiful to watch.” The incident became particularly notorious as it resulted in Heenan swearing live on air.
8. The ECW Promo That Shocked Wrestling (February 17, 1996)
Brian Pillman, alongside Joey Styles, delivers his controversial promo at ECW CyberSlam on February 17th, 1996. Photo Credit: WWE.
On February 17th, 1996, at ECW CyberSlam from the ECW Arena in Philadelphia, Pennsylvania, Brian Pillman made his first appearance since his controversial exit from WCW just six days earlier. When the arena lights came back on during a Joey Styles interview segment, Pillman stood in the ring to a massive ovation from the 1,300 fans in attendance.
The promo began with Pillman addressing Eric Bischoff, calling him a "gofer" and a "piece of ****." He then turned his attention to the ECW audience, labeling them "smart marks" before threatening to expose himself and urinate in the ring. The situation escalated when ECW owner Tod Gordon, booker Paul Heyman, and Shane Douglas rushed to intervene.
As security dragged Pillman from the ring, he produced a fork from his boot and attacked a planted audience member. The incident aired across three episodes of ECW Hardcore TV on February 20th, 27th, and March 5th, 1996.
While Pillman never wrestled a match in ECW, he made several more appearances, including a March 9th confrontation with Shane Douglas at ECW’s Big *** Extreme Bash. His final ECW angle featured him wrestling a six-foot pencil, mocking WCW booker Kevin Sullivan. The planned feud with Douglas never materialized, as Pillman signed with WWF in June 1996.
Eric Bischoff later revealed in his autobiography, Controversy Creates Cash, that Pillman’s ECW appearance was meant to build heat for an eventual WCW return, but Pillman instead leveraged the attention to secure wrestling’s first guaranteed WWF contract.
9. Brian Pillman’s Game-Changing WWF Press Conference (June 1996)
Brian Pillman signed his WWF contract at Titan Towers during a press conference that surprised the wrestling world in June 1996. Photo Credit: WWE.
In June 1996, Vince McMahon signed Brian Pillman to the first fully guaranteed WWF contract in company history. The three-year deal allowed Pillman to maintain his ECW commitments, personal merchandise rights, and operate his own hotline – unprecedented terms at the time.
The signing came after Pillman orchestrated an elaborate scheme involving WCW and ECW. While still technically employed by WCW through a verbal agreement with Eric Bischoff, Pillman convinced Bischoff to provide legitimate termination papers to make his "Loose Cannon" character seem more authentic. Pillman then used these papers to negotiate with WWF, playing all three companies against each other.
McMahon planned to debut Pillman as a surprise on Raw or King of the Ring, but news of the signing leaked to WCW. A press conference at Titan Towers was hastily arranged, though Pillman nearly missed it due to an ankle infection that hospitalized him days before.
At the press conference, with WWF President Gorilla Monsoon and executives Carl DeMarco and JJ Dillon present, Pillman displayed two distinct personas. On camera, he appeared humble and emotional about joining WWF. When the cameras seemingly stopped rolling, he unleashed an expletive-filled tirade against officials, claiming he could "do whatever he wanted" before swinging his crutch at a cameraman.
The segment concluded with a "concerned" WWF executive suggesting the company may need to find ways out of Pillman’s contract. While scripted, this marked one of WWF’s first steps toward edgier content that would define the upcoming Attitude Era.
10. The Steve Austin Interview That Changed Everything (October 27, 1996)
Brian Pillman conducts final interview with Steve Austin before an ankle-breaking incident, October 27th, 1996. Photo Credit: WWE.
Brian Pillman’s connection to Bret Hart ran deep. After his football career ended in 1986, Pillman trained in Stu Hart’s infamous "Dungeon" in Calgary, becoming a star in Stampede Wrestling, where he formed the successful "Bad Company" tag team with Bruce Hart. The Harts considered Pillman family, with patriarch Stu and matriarch Helen treating him like another son.
On October 27th, 1996, this family loyalty played into a pivotal WWF Superstars segment. While interviewing Steve Austin about his upcoming Survivor Series match against Bret Hart, Pillman praised his former mentor’s abilities, quoting Hart’s famous catchphrase, "The best there is, the best there was, and the best there ever will be." Austin, enraged by Pillman’s apparent allegiance to Hart, launched a brutal attack.
The assault culminated in what would become known as "The Pillmanizer" – Austin placed Pillman’s ankle between a steel chair’s seat and back, then leaped from the second rope onto the chair. The move legitimately aggravated Pillman’s existing ankle injury from an April 1996 car accident that had shattered his ankle. WWF used the angle to write Pillman off of television so he could undergo necessary surgery.
This interview laid the groundwork for the infamous Pillman firearm segment that would air just eight days later on Raw, pushing WWF programming into edgier territory.
11. The Infamous Pillman Incident on RAW (November 4, 1996)
The controversial moment Brian Pillman aimed a 9mm at Stone Cold Steve Austin during Raw’s home invasion angle. Photo Credit: WWE.
The November 4th, 1996, episode of Raw featured one of wrestling’s most controversial moments. After weeks of escalating tension between former tag team partners, Stone Cold Steve Austin vowed to confront Brian Pillman at his home in Walton, Kentucky.
Then-WWF interviewer Kevin Kelly conducted a live interview from Pillman’s residence, where Pillman, still recovering from ankle surgery, was surrounded by friends and family. When informed Austin was in the neighborhood, Pillman produced a firearm, declaring, "When Austin 3:16 meets Pillman’s 9mm, I’m gonna blast his sorry *** straight to hell!"
After subduing Pillman’s friends outside, Austin broke into the house. Pillman aimed the weapon while his wife Melanie and Kelly screamed. The feed cut to black, with director Kerwin Silfies reporting "a couple of explosions" to commentator Vince McMahon. When transmission resumed, Pillman shouted, "Get out of the ******* way!" – an unplanned expletive that made it to air.
The segment’s original script included more extreme elements that USA Network executives rejected, including Melanie Pillman taking a bump and on-screen gunshots. Despite pre-approval from the network, the realistic nature of the angle and accidental profanity caused immediate backlash. Nielsen ratings showed many young viewers switched to WCW Nitro during the segment.
The fallout was severe. USA Network CEO Kay Koplovitz demanded an emergency meeting with Vince McMahon. Multiple advertisers pulled their support, and the WWF had to temporarily tone down its programming. The incident marked WWF’s first major step toward edgier content, though it nearly resulted in Raw’s cancellation or relegation to a late-night time slot.
12. Joining The Anti-American Hart Foundation (March 1997)
Brian Pillman joins Bret Hart’s anti-American Hart Foundation stable alongside Jim “The Anvil” Neidhart, Owen Hart, and the British Bulldog Davey Boy Smith, post-WrestleMania 13, in 1997. Photo Credit: WWE.
After WrestleMania 13, Brian Pillman returned to align with his former Stampede Wrestling colleagues in a revamped Hart Foundation.
The new Hart Foundation consisted of Bret Hart, Owen Hart, British Bulldog Davey Boy Smith, Jim Neidhart, and Pillman – the only non-family member included in the stable. The group positioned themselves as anti-American heroes, receiving overwhelming support in Canada while drawing intense hatred from U.S. audiences.
On July 6th, 1997, at In Your House 16: Canadian Stampede in Calgary, the Hart Foundation secured its defining victory. In front of a rabid hometown crowd, they defeated the team of Steve Austin, Ken Shamrock, Goldust, and the Legion of Doom (Hawk and Animal) in a 10-man tag team match. The bout received widespread acclaim, with Dave Meltzer of the Wrestling Observer Newsletter rating it five stars.
The stable dominated WWF throughout mid-1997, holding every available championship – the WWF Championship (Bret), Intercontinental Championship (Owen), European Championship (British Bulldog), and Tag Team Championships (Owen and British Bulldog). Their reign ended abruptly with Pillman’s death on October 5th, 1997, followed by Bret Hart’s departure after the infamous Montreal Screwjob at Survivor Series.
13. The Controversial Marlena Storyline (August-October 1997)
Brian Pillman and Marlena during their controversial XXX-Files storyline, September 1997. Photo Credit: WWE.
The storyline began at SummerSlam 1997 when Brian Pillman lost to Goldust and was forced to wear Marlena’s dress until he could win a match. Frustrated by the humiliation, Pillman challenged Goldust to an "Indecent Proposal" match at Ground Zero: In Your House on September 7th, 1997, with two stipulations: if Pillman won, he would gain control of Marlena for 30 days; if he lost, he would leave WWF forever.
At Ground Zero, Marlena accidentally cost Goldust the match when her loaded purse backfired, allowing Pillman to claim victory. In the weeks that followed, WWF aired segments called "Brian Pillman’s XXX-Files," featuring a transformed Marlena – now dressed in black with a nose ring and slicked-back hair – appearing alongside Pillman. The storyline played on real-life history, as Pillman and Terri Runnels (Marlena) had dated during their time in WCW in 1990.
According to Terri Runnels, the storyline was set to culminate in a wedding ceremony on Raw where Goldust and Marlena would renew their vows. Pillman would interrupt during the "speak now or forever hold your peace" moment, attacking Goldust before Marlena revealed she had fallen in love with her captor. However, Pillman’s death on October 5th, 1997, forced WWF to hastily conclude the angle with a Jim Ross interview segment where Goldust abandoned Marlena, leading to her eventual alignment with Val Venis and the formation of Pretty Mean Sisters (PMS).
Pillman’s final televised match aired on the October 4th, 1997, episode of Shotgun Saturday Night, where he defeated “The Patriot” Del Wilkes by disqualification due to Goldust’s interference.
Brian Pillman: A Legacy of Innovation
From high-flying innovator to unhinged ‘Loose Cannon,’ Brian Pillman revolutionized professional wrestling in just 35 years. Photo Credit: WWE.
Tragically, on October 5th, 1997, Brian Pillman was found dead in his Bloomington, Minnesota hotel room before a scheduled match against Dude Love at Badd Blood: In Your House. He succumbed to an undiagnosed hereditary atherosclerotic heart disease at age 35 – the same condition that had claimed his father’s life. His final match took place the day before, losing to Goldust at a house show in St. Paul, Missouri. The following night on Raw, WWE held a ten-bell salute in his memory, though the episode would become controversial for an ill-advised live interview with his widow, Melanie.
Pillman’s impact on professional wrestling transcended his brief 35 years. From pioneering lucha libre moves in mainstream American wrestling to creating the first worked-shoot promos, his innovations fundamentally changed the business. The "Loose Cannon" character broke new ground in psychological storytelling, while his guaranteed WWF contract transformed wrestler-promoter relationships forever.
His influence continues through modern performers who blur reality and fiction, from CM Punk’s "pipe bomb" to MJF’s worked-shoot promos. Even his son, Brian Pillman Jr. (now known as Lexis King in WWE NXT), carries forward his father’s legacy of pushing creative boundaries.
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Samantha “Sami” Schneider-Crouse is a native of North Carolina and has been a pro wrestling fan since the age of 3. Her early favorites included André the Giant, Leilani Kai, the Jumping Bomb Angels, and “Macho Man” Randy Savage. A former dance teacher, she enjoys reading, writing, and spending time with her husband and three sons in her spare time.
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