In late 1985, Condrey joined World Championship Wrestling (WCW) alongside Bobby Eaton as the Midnight Express. In early 1986, Condrey and Eaton won the WCW World Tag Team Titles from the Rock 'n' Roll Express on Superstars on the Superstation and feuded with them until Condrey left the promotion in early 1987.
Condrey would team with Randy Rose in the American Wrestling Association (AWA) under manager Paul E. Dangerously. "Loverboy" Dennis and "Ravishing" Randy called themselves "The Original Midnight Express", and claimed the right to the name, which had since been used by Condrey and Eaton (and later by "Beautiful" Bobby Eaton and "Sweet" Stan Lane) in WCW.
They would defeat Jerry Lawler and Bill Dundee for the AWA World Tag Team Titles on October 30, 1987, in Whitewater, Wisconsin. They would have a two-month title reign, losing the titles to the returning Midnight Rockers (Shawn Michaels and Marty Jannetty) on December 27, 1987 in Las Vegas, Nevada.
Condrey returned to WCW in November 1988, alongside Randy Rose and Paul E. Dangerously.
During the November 5 episode of World Championship Wrestling, Jim Cornette received an anonymous phone call. The caller ridiculed Cornette over Eaton and Lane's loss of the WCW World Tag Team titles to the Road Warriors on October 29. Cornette recognized the caller and basically asked him to come say it to his face. At that point, Dangerously and the Original Midnight Express hit the ring and proceeded to pummel Cornette and Stan Lane, who was wrestling in a singles match. By the time Bobby Eaton showed up, it was three on one. Cornette showed up the next week carrying his blood stained suit jacket and the feud was on.
The teams wrestled at Starrcade '88, but nothing was solved. This built up to a 6-man tag match involving the managers on pay-per-view in February 1989. Condrey left WCW once again soon thereafter.