Early career (1984–1989)
Calaway made his debut in 1984 for World Class Championship Wrestling under the ring name "Texas Red". He wrestled and lost his first match against Bruiser Brody. In 1988, after four years in the promotion, he left and joined the Continental Wrestling Association (which became the United States Wrestling Association after Jerry Jarrett merged CWA with WCCW), wrestling under several gimmicks. On April 1, 1989, he was booked to win his first professional wrestling title, the USWA Unified World Heavyweight Championship, defeating Jerry "The King" Lawler, under the stage name "The Master of Pain". While performing as "The Punisher", Calaway won the WCWA Texas Heavyweight Championship on October 5, 1989 when Eric Embry forfeited the title.