In early 1989, Teddy Long was a referee for World Championship Wrestling, but due to a series of questionable calls, including one that cost the Road Warriors their World Tag Team Championships, Teddy Long was fired and took up managing instead.
Long paired Dan Spivey with Sid Vicious, two people who had recently signed with WCW and gave them the name “The Skyscrapers” due to their height.
The Skyscrapers’ first taste of success came at the 1989 Great American Bash pay-per-view where they first co-won a two-ring King of the Hill battle royal with Sid being the survivor in one ring and Dan surviving in the other. The rules called for the two to fight each other but manager Teddy Long convinced them to shake hands and share the prize money before getting on the microphone and telling the crowd that what they had that the other tag teams didn't have was unity. Later in the night, the Skyscrapers defeated The Dynamic Dudes (Johnny Ace and Shane Douglas) due to their overwhelming size and power.
The Skyscrapers quickly became involved in a feud with the Road Warriors, sparked by Teddy Long's actions while still a referee. The two teams were very evenly matched in power and intensity creating a series of matches that did not favor one team over the other. Spivey and Vicious were disqualified against the Road Warriors at Halloween Havoc 1989, but neither team looked like losers on the night. Shortly after Halloween Havoc, the Skyscrapers faced the Steiner Brothers at Clash of the Champions IX in a hard hitting match.
With Vicious out of action, Teddy Long brought in another tall newcomer in the same mold as Sid Vicious and Dan Spivey and dubbed him ”Mean” Mark Callous. The New Skyscrapers immediately picked up the feud with the Road Warriors and kept on having inconclusive matches with them. At Clash of the Champions X, the Skyscrapers finally got the better of the Road Warriors, not in the match but afterwards when they beat the Road Warriors down. At this point in time, no one had ever been able to physically dominate the Road Warriors, something that pointed that big things had been planned for the Skyscrapers. But big things never happened, as in the days before the scheduled Chicago Street Fight at WrestleWar 1990, Dan Spivey suddenly left WCW.
Instead of cancelling the announced match, The Masked Skyscraper debuted as a replacement for Spivey. The Road Warriors made short work of Callous and the Masked Skyscraper, ending the feud and ending the Skyscrapers run of domination. Callous decided to go on his own for a while but failed in a challenge to WCW United States Heavyweight Champion Lex Luger.
By the end of 1990, Spivey returned to WCW television. The Skyscrapers briefly reunited at Starrcade 1990 as he and Sid Vicious took on and beat The Big Cat and The Motor City Madman. The match was the only time Spivey and Vicious teamed up to reform the original Skyscrapers.