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The peak of the Professional Wrestling industry's success, the Monday Night Wars refers to the period of time from 1995 to 2001 when WCW's Monday Nitro went head-to-head with the WWF's Monday Night Raw.
It all started when Eric Bischoff was approached by Ted Turner and asked what he believed WCW needed to do to overtake the WWF. Bischoff's on-the-spot suggestion was a weekly timeslot on Mondays to directly compete with Raw; in 1995, he got what he wanted - Nitro hit the air directly opposite Raw, and the War was on. At the time, Nitro was live every week, as opposed to Raw being pre-taped days (or weeks) in advance, which allowed Bischoff to reveal the results of Raw on Nitro (a move that, later, would come back to bite him on the ass). In response to this, WWF eventually transitioned into turning Raw into a live broadcast.
For a period starting in mid-to-late 1996 and continuing until early 1998, Nitro would routinely defeat Raw in the ratings, mainly due to the ultra-hot "New World Order" angle. As Eric Bischoff famously put it, WCW beat the WWF for "eighty-four weeks in a row". Facing bankruptcy and defeat square in the face, the WWF fired back in 1997: starting around the time of the Montreal Screwjob, the company started to become Darker and Edgier (a move inspired by the success of ECW) and went into what they called the "Attitude Era". With WWF's adult-oriented fare competing with WCW's more family-friendly product, WWF eventually took the lead in the ratings.
In the last great shot of the War, WCW pulled the trigger on what could have been their biggest moneymaking feud/match of the year in July of 1998: live on Nitro, then-US Champion and up-and-coming superstar Goldberg defeated "Hollywood" Hulk Hogan to win the WCW World Heavyweight Championship. Despite winning the ratings battle that night, it was done at the cost of a ton of potential PPV revenue; many consider the move to be the beginning of the end of WCW.
Of course, the event that really sent WCW into a downward spiral was the Finger-Poke of Doom: the combination of a Shocking Swerve ending to a world title match that led to the reformation of the nWo, coupled with the half-million viewers Nitro lost when it was revealed Mick Foley was winning his first WWF Championship on a pre-taped episode of Raw (with WCW announcer Tony Schiavone famously remarking "That'll put butts in seats"), was the killing blow for the promotion. It just took them two more years to really die out.
In the meantime, the WWF flourished thanks to the Attitude Era and WCW's missteps - wrestlers like Stone Cold Steve Austin, The Rock, Mick Foley, Triple H, The Undertaker, and Kane practically became household names, and the company's success positioned them as the most powerful wrestling promotion on the planet. On the flip side, WCW kept pushing the nWo angle for far longer than it should have, and it failed to build new stars who could ultimately replace the older stars on the roster (mainly because those older stars were often members of the company's booking team), leading its product to become stale and boring to many, which led to the company beginning to lose viewers at an astonishing rate.
From 1999 to 2001, WCW tried - and failed miserably - to mirror the WWF's successful changeover to the Attitude Era, doing everything from hiring Vince Russo to instituting a Hardcore Title to trying to cross-promote the company with music and movie stars (including its infamous decision to make David Arquette the WCW Champion). But sadly, it was too little too late; after the AOL/Time Warner merger went down, WCW was put up on the chopping block, seen as little more than a financial drain on its parent company. With Ted Turner no longer in a position to protect WCW, and with the company unable to turn around its fortunes, it was eventually sold - to the WWF. (Eric Bischoff tried to purchase the company in the weeks prior to its sale to the WWF so that he could eventually reboot the entire promotion, but those plans eventually fell through.)
The Monday Night Wars ended on March 26, 2001, when WCW held the final Monday Nitro; in a surreal sight, Vince McMahon appeared live on both Raw and Nitro as part of a special simulcast (Vince was in the arena where Raw was being held), and then it was revealed that Shane McMahon - who was at Nitro - had (kayfabe) bought WCW instead of his father. This led into the InVasion angle, which would eventually put WCW to rest for good.
With the arrival of Hulk Hogan and Eric Bischoff in 2010, TNA eventually moved their show Impact to Monday nights, in direct competition with WWE's Raw. At first glance, it appeared that they were trying to reignite the Monday Night Wars all over again, but with Impact getting only a third of the ratings of Raw (at best), it never achieved the same effect as the WCW had during the original war. TNA eventually stopped trying to compete, moving Impact back to Thursday. It received the 2010 Gooker Award from Wrestlecrap.
WWE eventually created a "Monday Night War" DVD covering this timeframe in wrestling history, and the The Rise and Fall of WCW DVD set covered the Monday Night Wars as part of WCW's overall history. WCW's final years were also covered in the book The Death of WCW (co-authored by Wrestlecrap writer RD Reynolds), which examined many of the problems and decisions that led to WCW's ultimate downfall.