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The original was posted on /r/squaredcircle by /u/topsy_krett_guy on 2025-12-05 15:57:40+00:00.
February '99, Big Show gets brought in under his real name as McMahon's enforcer in the Corporation stable.
A month later he's renamed to the Big Show and fights Mankind for the right to referee the match between Rock/Austin at WM but gets DQ'd. McMahon is pissed, slaps him, then gets punched in retaliation. Show turns face.
Show, Mankind, Test, and Shamrock then form the short lived Union stable to combat the Corporation.
By the summer he turns heel again and forms a short lived team with The Undertaker. They win the tag titles but lose them again one night later (a recurring theme of the Attitude Era). Then they win and subsequently lose them again less than a month later.
The Taker/Show team is done with as Taker is out with injuries, leading Big Show into the infamous Big Boss Man feud where he surfs on his father's casket as its dragged by Boss Man.
By Survivor Series he replaced Austin after the infamous angle of Austin being run over by a car (where a certain thong-wearing fatty DID IT FOR DA ROCK), winning the WWF title until losing it in January to HHH.
Then Royal Rumble 2000 happens, with the controversial ending where Rock's feet clearly hit the ground before Big Show's, leading to the two feuding over who gets the guaranteed WM title shot. After a bunch of shenanigans lead to the WM main event being a fatal 4 way elimination match between HHH, Rock, Foley, and ~~Steven Richards~~ Big Show...Big Show is the first eliminated.
Then within the next month Big Show is reduced to a comedy gimmick where he impersonates other wrestlers (Showkishi, The Showster, etc.) until he feuds with Shane McMahon and loses a Falls Count Anywhere match.
He's gone for a few months and returns, only to randomly turn heel again by attacking the Undertaker and siding with Shane. He gets thrown off the stage by the Undertaker, and is then sent to developmental training in OVW for the rest of the year.
The first year/year-and-a-half of his WWF career was absolutely insane. He shifted between face and heel about 8 different times (which I know is a recurring gag in his career, but the fact he had so many in just the '99-'00 span alone is crazy). Won the WWF title but was reduced to a low card comedy gimmick less than 3 months later, and then ultimately is sent away to work in OVW after being told about weight problems in real life.