He spent the early 1980s with the National Wrestling Alliance under their Championship Wrestling from Florida territory promotion where the legendary Gordon Solie was the head announcer. Windham was a fan favorite (face) for most of his early career, having great success in singles and tag matches on the back of his ability to go 20-30 minute matches without needing to be an over-the-top cartoon character like Hogan, Savage or Flair all did. Windham became a tag team partner with his own brother-in-law Mike Rotunda. They went to the WWF in '84-'85 where the team of Windham and Rotunda were branded The U.S. Express and they quickly made an immediate impact in the WWF's tag team division title picture. Windham's best moment in his first WWF run was at the very first WrestleMania (1985) when he and Rotunda dropped the Tag Belts to The Iron Sheik and Nikolai Volkoff. Windham's tenure with the WWF ended when he couldn't cope with the extreme travel that the WWF was doing, as he was used to working the territories as he had before. Being Blackjack's kid, Barry was said to have been perceived as a rebellious flake who didn't really care about burning bridges with wrestling promoters as he always found a better home in Florida. But the problem was that the WWF was not the home for NWA-esque workers as it was about the cartoon characters, but Windham could still be himself because The U.S. Express was its own character.
After departing from the WWF, Windham returned in the NWA's Florida territory still a babyface where he fought Ric Flair and feuded with Ron Bass. By the Fall of 1986, he shifted to the NWA's Jim Crockett Promotions (JCP) territory again a face where he had many memorable matches with "The Nature Boy" Ric Flair, including some when their matches went to 60 minute time limit draws and even some extending beyond an hour of action, which just showed how much capable Flair was, nobody called him the Marathon Man for nothing. And Windham did more than his fair share of the work as well to make it work for everyone involved. After a series of epic matches with Flair, Windham reverted to the tag team division where he teamed with Ronnie Garvin. The Midnight Express were the biggest constant enemies Windham and Garvin ever fought as a tag team. Windham even got to form an alliance with a young Lex Luger, who went heel and turned his back on Windham to do so, in order to fulfill his aspirations to join up with The Four Horsemen. Rather than enter the annual Jim Crockett Memorial Tag Team Tournament (also known as the Crockett Cup), Windham and Garvin were split up. Ronnie Garvin instead teamed up with Jimmy Garvin, and rather than have Windham seek another partner, he was booked to battle Ric Flair for the NWA World Heavyweight Championship Belt in what would be another classic match between the two. Flair defeated Windham with a controversial pinfall after a little over 25 minutes of action. Windham spent the remainder of 1987 as a singles midcard performer where he won the short-lived NWA Western States Heritage Championship Belt and defended it against the likes of a young Rick Steiner of the Varsity Club, Big Bubba Rogers, and Incubus. However, 1988 would mark the epic shocking moment that nobody at the time could ever seem to expect. Luger was just kicked out of the Four Horsemen. First, he (Luger) blamed Horseman manager, J.J. Dillon, for costing him the U.S. Title when Dillon's attempt to help Luger win the match, by cheating, backfired. Lex subsequently did not allow Dillon to win a Bunkhouse Stampede match, as the Horsemen had agreed to rig the Bunkhouse Stampede just for Dillon, not Luger, because Luger kayfabe didn't conform to the Horsemen rules, so the young hotshot had to be tossed aside for a guy nobody expected to join the Horsemen. In a moment of shock, Windham betrayed the newly-turned face Luger in favor of Arn Anderson and Tully Blanchard taking the NWA Tag Team Championship Belts away from the short-lived duo of Windham and Luger. In addition, the newly turned heel Windham started to incorporate a black glove as well as the clawhold as his finisher, taking a signature move after his legendary father Blackjack Mulligan, and as a result of his heel turn, Windham joined The Four Horsemen and aligned with his former rival Ric Flair, Arn Anderson and Tully Blanchard. Windham again went back to singles where he was a dominant NWA United States Champion, defending it against the likes of Brad Armstrong, Sting, Dusty Rhodes and Bam Bam Bigelow before dropping it to Lex Luger at Chi-Town Rumble on February 1989. Windham's contract expired in March 1989.
For the second time, Windham returned to the WWF for his second stint in 1989, as The Widowmaker. Despite the nickname, Windham still had the cowboy image, now he was just playing a generic cowboy heel. Only this time, Windham wasn't truly allowed to get over with the WWF fans doing 20-30 minute matches. No, Windham had to get over via character, and all he had going for him in terms of character and image was the fact that he was just an ordinary cowboy and nothing else so he wasn't cartoonish enough. He was supposed to have been on Randy Savage's 1989 Survivor Series team, but was replaced by "Earthquake" John Tenta. Windham left the WWF, but this time, the accepted notion for his second departure was that Blackjack Mulligan and Barry's brother Kendall Windham were in trouble with the law even though they were framed for counterfeiting. Some criminal gave Blackjack and Kendall the cash, and they were the ones caught with the cash so they had to spend time in prison from 1990 to 1992, that's why Barry understandably left. Another version of this departure is that Barry again didn't like being on the road 300+ days a year for the WWF.
In May 1990, Windham joined World Championship Wrestling (WCW) and reunited with The Four Horsemen, who were now composed of Ric Flair, Arn Anderson, Sid Vicious and brought back Ole Anderson. By then, Ole was semi-active but converted into a full-time manager once Windham returned. In addition, they were now flanked by "Woman" Nancy Benoit as well. That Horsemen lineup were now feuding with the likes of Luger, Sting, Rick Steiner, Scott Steiner, Paul Orndorff, Junkyard Dog and El Gigante. His best moments throughout his second stint with the Horsemen in '90-'91 were a controversial Halloween Havoc 1990 match between Sting and Sid Vicious where Windham deliberately dressed up as Sting, and let Sid pin him easy. Once Windham's facade was noticed, the match was restarted, and the real Sting defeated Sid Vicious fair and square, doing a series of vignettes with Arn Anderson in preparation for their tag match against Doom (Ron Simmons and Hacksaw Butch Reed) in an Atlanta ghetto. A famous quote from Arn Anderson to Barry Windham, "Ya know something BW, when I took a look at this dump, it ain't the Helmsley college, pal!." Barry responds, Ya, but it's a lot cheaper!", and also Windham's involvement in the Yellow Dog saga where Brian Pillman was under the thumb, noting that if Pillman was unmasked, he'd be banned from WCW forever. But if Yellow Dog was not Pillman, then he'd be reinstated. By the end of late 1990/early 1991, The Four Horsemen once again broke up abruptly as Jim Herd rubbed Sid Vicious and Ric Flair the wrong way, and both left the WWF. That left Windham and Arn Anderson as the remaining members, and Herd intended to shift Flair down the midcards while Luger gets his big break as the WCW's main heel, with Windham going back to being a face for the first time since 1988, in what can only be an unnoticed reverse double-turn. At the end of the GAB '91 PPV, Windham became a face, while Luger now took on Harley Race and Mr. Hughes as his managers, and Arn Anderson was now confined to teaming with Larry Zbyszko as The Enforcers, allowing Arn a chance to step out of Flair's shadow now that Flair was out of the WCW for the upcoming Dangerous Alliance storyline in '91-'92. Windham was sidelined with a broken hand after Arn Anderson and Larry Zbyszko slammed the car door on him, and at the time, Windham was teaming with a young Dustin Rhodes (the pre-Goldust version of Dusty's son). The Windham/Rhodes tag team would eventually come to an end when Windham again turned heel in '92-'93 after Rhodes refused to pin Ricky Steamboat after an accidental low blow against the team of Steamboat and Shane Douglas. At the end of 1992, Windham now teamed up with his former rival Brian Pillman, who had also recently turned heel, and went from a courageous underdog babyface to a pretty bad boy with a bad attitude-type heel no different than Shawn Michaels' HeartBreak Kid heel character over in the WWF, and if Bill Watts hadn't lowballed The Steiners in favor of scouting to bring back Ric Flair, maybe Scott Steiner would've been another heel turn in late 1992, as Rick's little brother was due for a significant heel push at the time, so three strikes of heel turns in late 1992 happened to Windham, Pillman and Steiner all at the same time. For a little while, Windham and Pillman teamed together to reclaim the WCW Tag Team Championship Belts that he (Windham) and Rhodes lost, before Windham became a full-time singles wrestler for good in 1993. Windham pursued the NWA World Heavyweight Championship Belt at a time when the NWA Belt was now nothing more than a second-rate championship belt to the WCW World Heavyweight Championship Belt. After beating The Great Muta to win it, the returning Ric Flair (now a face) tried to present Windham with the belt, but Windham took the belt and walked away. Around that time in '93-'94, Flair and Arn Anderson were now trying to recruit Barry Windham to come back to the face incarnation of The Four Horsemen. Windham now declared himself The Lone Wolf after declining to rejoin. After successful title defenses against Anderson, Muta and Flair, Windham incurred a torn knee ligament and ultimately, his prime ended in '93-'94 when he had to spend almost the whole '93-'94 on the sidelines, and when he came back in 1994, Windham was no longer a lanky-looking cowboy as he wound up piling on his weight gain and also because injuries and his Four Horsemen-esque lifestyle were finally catching up to him. A bigger chunkier Windham (revealed to be a short-lived member of Col. Robert Parker's Stud Stable) returned to take on Flair (a tweener who was set to go heel at BATB '94) at Slamboree 1994. For weeks leading up to the Flair/Windham 1994 match, many WCW fans believed Hulk Hogan would be coming to take on Flair, as the saying was framed as a 6'7, 300 pound former World Champion with blonde hair was the masked man that Col. Parker brought in to challenge Flair. Flair won again, and Windham reaggravated his knee injury, and this time, Windham would end his third stint with WCW as he dropped out of sight for the next two years as he was recovering from another knee injury.
Windham returned to the WWF for the third and final time in 1996, this time as The Stalker. He was supposed to have had a feud with Marc Mero, as the former was to stalk Sable, but Mero vetoed it, and so The Stalker was now introduced with very little fanfare as a face. For a short time, Windham renewed his feud with Rhodes (now known as "The Bizarre One" Goldust), and in one of his throwaway matches with Rocky Maivia (later known as the future "The Rock" Dwayne Johnson), Windham at 36 was looked at as mailing it in with his performances, as he wore an old high school vintage WWF t-shirt to hide his lack of lanky definition. For 1997 and early 1998, Windham had a failed homage to his father when he teamed up with Blackjack Bradshaw before Windham joined Jim Cornette's old-school NWA stable. Unlike his other two WWF stints, his third WWF stint saw Windham as a shell of his former self, but ironically enough, Windham was willing to play ball and stick around for the WWF, even though it wouldn't lead to much success for Windham himself in the end.
After '97-'98, Windham returned to WCW as he was brought back by Eric Bischoff, who had him turn against Ric Flair and The Four Horsemen in favor of joining the nWo Hollywood faction led by Hollywood Hogan. Although, Bret Hart wasn't the only fully-indoctrinated nWo B&W member, as Windham also wasn't fully-integrated into the nWo Hollywood faction in late 1998 before forming a tag team with Curt Hennig. In 1999, Windham again reinjured his knee but would return as part of The West Texas Rednecks where they were supposed to be a heel group feuding with Master P's No Limit Soldiers stable, but due to WCW being a southern promotion, the southern WCW fans liked the Rednecks as if Hennig and Windham were fan favorites. The West Texas Rednecks were composed of Curt Hennig, Barry Windham, Kendall Windham, Bobby Duncum, Jr. and "Virgil" Mike Jones. At the end of 1999, Windham left WCW for the last time as he and his brother Kendall were released from their WCW contracts.
Critics also assumed that when he joined The Four Horsemen, Windham started to let himself go a little, got immersed into living the Four Horsemen lifestyle away from the ring via partying, expensive fashion, fancy travelling, hotel rooms and all other stuff, turning him from Blackjack's kid into a party animal and a dirty macker womanizer, but his partying effects didn't really effect him as badly as it eventually badly happened to him by 1994. Normally, wrestlers in their 30s were courted to be the top draws in wrestling companies just to see if they are up for the task as a top draw so therefore it's considered the wrestler's average prime years, but Windham threw away his monster talents right before he became a 30+ year old. So after his 1990 WCW return, Windham went from being a great 1980s NWA performer to an early 1990s WCW performer who was decent despite losing a few quality steps until his torn knee ligaments in '93-'94 and subsequent weight gain stemming from womanizing, drinking and living the general Four Horsemen lifestyle. After '93-'94, Windham lost his lanky look, and it was easier for many of his former fans to think of it as Windham throwing away his monster talents down the toilet drain. So now we wind up with a career of a professional wrestler who looked like he could've done more to assert himself to become a World Champion caliber megastar but for various reasons fell short of what was expected of Barry Windham.
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