Dennis Condrey started wrestling in 1973 in the Tennessee territory. He moved on to Alabama's Southeast Championship Wrestling and formed the Midnight Express in 1981 with Randy Rose and Norvell Austin. They dominated the tag team scene there until Condrey left for Mid-South Wrestling in 1984. Once there, he formed a new version of the Midnight Express with Bobby Eaton with Jim Cornette as their manager. They also started a legendary feud with the Rock 'n' Roll Express that carried over into the NWA's Jim Crockett Promotions in 1985.
In early 1986, Condrey and Eaton won the NWA World Tag Team Titles from the Rock 'n' Roll Express and feuded with them until Condrey left the promotion in early 1987. He literally left overnight, giving no notice to Cornette, Eaton, or the NWA.
Condrey would reunite with former partner Randy Rose in the 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 the NWA.
They would defeat Jerry Lawler and Bill Dundee for the AWA World Tag Team Titles on October 26, 1987, in Memphis, TN. 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, NV.
At the request of Cornette, because his team of Eaton and Lane didn't have a program after their feud with the Road Warriors ended, convinced head booker Dusty Rhodes to give Condrey a second chance with Randy Rose and Dangerously in a "Midnight vs. Midnight" feud. Condrey and Rose resurfaced in the NWA (with Dangerously) in late 1988. During a television broadcast on TBS at the Techwood Drive Studios in Atlanta, Jim Cornette received an anonymous phone call. The caller ridiculed Cornette over Eaton and Lane's recent loss of the NWA World Tag Team titles to the Road Warriors. 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 on TBS carrying his blood stained suit jacket and the feud was on.
The teams wrestled at Starrcade '88, but nothing was solved. The Midnights vs. Midnights would be the hottest feud in the NWA for months, building up to a 6-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, due to changes in ownership, the NWA was going through booking upheaval with Dusty Rhodes being replaced as head booker by George Scott. Jim Crockett already had a problem with Condrey due to his previous overnight disappearance and Scott had previous animosity with Rose, so Scott's appearance as top booker made for the catalyst to bury the team and the feud. The feud was cooled off and the "loser leaves town" match was going to be used to kick one of them out of the territory once and for all and continue to bury the other. At the last minute, Dennis Condrey once again decided to leave the NWA, rather than take his PPV payoff and give Crockett and Scott the satisfaction. Jack Victory was brought in as his replacement and the match went forward.
Condrey returned to Alabama (now known as Continental) in the Spring of 1989 and would become the CWF Heavyweight Champion. He would also form a short-lived tag team called the "Lethal Weapons" with Doug Gilbert before retiring from full-time action in the early 1990s
Condrey came back to team with Eaton in 2004 and, along with Stan Lane, they have been wrestling as the Midnight Express in the independents and feuding with the Rock 'n' Roll Express and The Fantastics.