So Bad It's Horrible/WCW

WCW was once the second-most popular wrestling/sports-entertainment promotion in the United States (and even beat its chief rival, WWE, for a decent stretch of time), but it made so many mistakes that Wrestlecrap and Figure Four Weekly were able to write a book about the company's downfall (The Death of WCW).

The sheer amount of terrible angles, Gimmick Matches, backstage politics, Vince Russo booking, and horrendous business decisions led to a company worth $500,000,000 and backed by Ted Turner becoming a hollow shell of a promotion bought by Vince McMahon for just $3,000,000.

Championships

 * To promote the film Ready To Rumble, WCW allowed actor David Arquette to win their heavyweight title, keep it for a good clip of time, then turn heel as part of one giant Shocking Swerve (with overzealous announcer Tony Schiavone branding it "the ultimate swerve"). This was the angle that cemented booker Vince Russo as being certifiably insane amongst wrestling fans. Even Arquette protested it, since he knew it would infuriate the fans, but it was in his contract. Arquette also quietly donated the paychecks he received during his WCW tenure to the families of Owen Hart, Brian Pillman, Bobby Duncum Jr., Brian Hildebrand (all deceased), and Darren "Droz" Drozdov (paralyzed from the waist down following an in-ring accident).
 * As bad as David Arquette as WCW champion was, it was only the second most idiotic championship reign in WCW history—second only to Vince Russo's. Yes, Russo gave himself the WCW Championship not long after he gave it to Arquette. Unlike Arquette, he felt absolutely no regret for doing it and could've stopped it from happening at any time because he was one of the bookers. Vince Russo is, to this day, one of the most despised figures in wrestling. Imagine that.

Pay-Per-Views

 * There's WCW's Great American Bash 1991 PPV, which had the entire Baltimore audience switching back and forth between two reactions—sitting on their hands and chanting "WE WANT FLAIR!" (especially during the main event) to protest Ric Flair's firing from WCW just days before the event. Flair, meanwhile, would join the WWF, taking the NWA World Heavyweight Championship with him (because he wasn't paid back the $25,000 deposit he put down on the belt when he received it for the first time) and calling himself "The Real World's Heavyweight Champion" (a Take That aimed at then-WWF champ Hulk Hogan and at booker Jim Herd, who was running WCW at the time).
 * The real "beginning of the end" may have taken place about a month prior to Starrcade 1997. In a backstage locker room meeting, Eric Bischoff declared that Vince McMahon would be out of business within six months, then declared that Hulk Hogan, Roddy Piper, and Randy Savage are his only real draws (in an attempt to reign in Scott Hall and Kevin Nash's egos). Bischoff's boast does little to reign in Hall and Nash's egos and it alienates Ric Flair in the process. Six months later, at the time when the WWF was supposed to be finished:
 * Flair no-shows a taping of WCW Thunder against Bischoff's orders to watch his son, Reid, compete in an amateur wrestling tournament. (To be fair, Ric gave plenty of advance notice; when they ignored his scheduled day off, Ric ignored them in return. The bright side: Reid took first place in his division.)
 * Flair no-shows the following Nitro, assuming Bischoff made good on his threat to fire him.
 * Bischoff calls another locker room meeting and threatens to sue Flair.
 * Nitro's long winning streak in the ratings war comes to an end that very night.

Angles & Gimmicks

 * The Shockmaster, a wrestler whose career literally ended in seconds. For weeks, a mystery man had been built up as the difference maker in a huge WCW feud. During the mystery man's introduction on a WCW pay-per-view, The Shockmaster broke through a wall (he was big and strong, see?)...and tripped over the edge of the hole, landing on his face and losing his helmet (which exposed him as Fred Ottman, better known as Tugboat or Typhoon). The only difference he made was sinking the angle and his career. Oh, and the helmet he lost? A Stormtrooper Halloween mask covered with purple glitter. That's right, even his costume sucked.
 * Ric Flair and Davey Boy Smith (who were part of this angle) promptly ran backstage to avoid breaking character in front of the audience, and even Jesse Ventura (on commentary) laughed himself sick. Sid "Vicious" Eudy deserves some kind of medal for being able to keep a straight face during his subsequent conversation with Shockmaster.
 * Appropriately enough, the "Shockmaster" angle was quite literally a Wall Banger. What makes this whole thing even more hilarious was the whole buildup that got the crowd into the whole thing; when Sting announced the partner's name "The SHOCK. MASTER!!" and the whole thing kicked off, you could hear the crowd cheering like crazy for the guy who would save the faces in this match. When Ottman came barreling through the wall and faceplanted, the entire crowd went absolutely dead.
 * The Stacy Kiebler/"Miss Hancock" pregnancy angle is fortunately a subversion, as WCW was mercifully taken behind the woodshed before the angle could come to a conclusion. If it had, the father of her child would've been revealed to be Vince Russo.
 * Russo and Ed Ferrara's angle of "Oklahoma", which consisted of Ferrara dressing up as a parody of Jim Ross complete with BBQ sauce and mocking JR's Bell's palsy (and calling matches just by yelling things repeatedly), was a completely tasteless gag that nobody thought was funny; many people within the company (including Ric Flair) were outright pissed that Russo and Ferrara would do something so utterly crass. You can even hear Tony Schiavone utter a legitimately shocked "Oh, no." the first time Oklahoma came out during Mayhem 1999, and he seems beside himself the whole time the mockery is going on.
 * Even Ed Ferrara has since admitted that the whole thing was in horrible taste. When Jim Cornette slapped him across the face, Ferrara admitted that he deserved it rather than retaliating.
 * Jim Herd was the president of WCW during the early part of the 1990s. He had no previous experience with wrestling, and despite Flair being a world-famous World Champion, was convinced that Flair was too old to draw. First he tried to Retool Flair into a Roman gladiator named Spartacus (to which Kevin Sullivan famously replied "while we're doing this, why don't we go down to Yankee Stadium and change Mickey Mantle's number?"). Then he simply fired Flair. The problem? Flair was WCW World Heavyweight Champion at the time. And since he had put down a $25,000 deposit on the belt, which WCW did not refund to him after he was fired, Flair decided he owned the physical title belt. He then showed up on WWF television with the WCW belt. Flair went on to be promoted as "The Real World Champion" by heel manager Bobby Heenan and work a great (and financially successful) program with Hulk Hogan. WCW, on the other hand, was devastated by the loss of their top draw and their inability to find anyone to replace him. At the nadir, fans were ignoring the actual matches and chanting "We Want Flair". Herd would eventually resign in disgrace.
 * In the 1990s, Tony Schiavone was an adequate, if not good, commentator with a pair of bad habits in irrational exuberance and calling just about every move he didn't know the name of a "face jam". But as WCW hit the skids and management began to fall apart, so did Schiavone's commentary. Part of this was due to the Enforced Method Acting that WCW used on the commentators to keep their commentary "more spontaneous" - they never allowed them to see the pre-taped segments, so they would then not know how to sell them and make stupid comments. However, Schiavone was bad enough on his own. He proclaimed every episode of Nitro to be "the greatest (moment/night/event) in the history of our sport!", for which he (and the phrase) was mocked mercilessly by smarks and marks alike. He also proclaimed just about everything "the most shocking swerve ever" after Vince Russo came in. This went over even less well, and was so mocked it became a Trope of its own.
 * The Fingerpoke of Doom is often labeled as the pivotal moment (though by no means the only moment) that led to WCW's collapse in 2001, made worse because there were several ways the promotion could've saved the angle (such as not destroying their top draw at the time), but on the bright side at least it had a Trope named after it. At the end of the telecast, the fans made their displeasure known by throwing all manner of bottles and trash into the ring.
 * As an added bonus: on that same show, Tony Schiavone launched a Take That at Mick "Mankind" Foley and the WWF, revealing that he was going to win the WWF Championship and sarcastically proclaiming "that'll put some butts in seats". Hundreds of thousands of fans immediately switched over to Raw; throughout the next few months, signs showed up on Raw that said "Mick Foley put my ass in this seat". In Schiavone's defense, he was ordered to say it by Bischoff despite not wanting to.
 * The famous attempt to play Booker T and his brother Stevie Ray as what appeared to be slaves (they were called "The Posse" and supposed to be convicts). Stevie was to be called "Kole" and Booker was to be called "Kane". This was tried at a house show and met with such vehemence that it never made it to TV, as the image of two black men in shackles led to the ring by Col. Rob Parker (a rich white Southerner) raised way too many red flags. Booker and Stevie did initially come out as Kane and Kole, just not with the slave gimmick.
 * The infamous "Drunk Scott Hall" angle from 1998 is seen as this by many now, with no help whatsoever from Real Life Writing The Plot. Lowlights included Hall collapsing and stumbling around the ring (often while slurring promos), some very awkward "acting" from other wrestlers (especially Kevin Nash) and, of course, Hall "vomiting" on Eric Bischoff. Hall's ex-wife went so far as to write an open letter on the subject, which says something regardless of Hall's more recent problems.
 * It seems ironic that WCW tried to regain the lead in the Monday Night Wars through one man whom WWE had reused earlier with limited success, The Ultimate Warrior. Warrior's stint in WCW did not go well, from a needlessly long and confusing introduction dashed with various motifs blatantly stolen from Batman to his lacking in-ring skills, fans were treated to a show that was goofier than ever. The climax was a notoriously bad match between Warrior and Hulk Hogan at Halloween Havoc 1998, which Hogan won after a cheap run-in. Just to make things that little bit worse, Warrior had a number of perks and high pay hardly matching his lax workload in his contract. Also of note is that Davey Boy Smith badly injured himself on a trap door that Warrior used to enter the ring and was later fired via Fed Ex.