Rose joined the American Wrestling Association (AWA) in 1987. Known as "Ravishing" Randy Rose, he and Dennis Condrey called themselves "The Original Midnight Express", and claimed the right to the name, which had since been used by Condrey and Bobby Eaton and later by Eaton and Stan Lane. The duo were managed by Paul E. Dangerously. Condrey and Rose defeated Jerry Lawler and Bill Dundee for the AWA World Tag Team Championship 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 and Rose resurfaced in World Championship Wrestling (with Dangerously) in November 1988. During the November 5 episode of World Championship Wrestling, Jim Cornette had received an anonymous phone call. The caller ridiculed Cornette over Bobby Eaton and Stan Lane's loss of the WCW World Tag Team Championship to The Road Warriors on October 29. Cornette recognized the caller and 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. The Midnights versus Midnights would be the hottest feud in WCW for months, building up to a six-man tag match involving the managers on pay-per-view in February 1989. The one who got pinned would have to leave the promotion. However, WCW was under new ownership and in transition at the time and many wrestlers were coming and going. At the last minute, Condrey decided to leave WCW. Jack Victory was brought in as his replacement and the match went forward. Rose would leave WCW for a time and Dangerously would go on to bring in the Samoan Swat Team as his new team. Rose would return to WCW for a brief time in mid-1989.