Brian Lee made his debut in 1988 for Jerry Jarrett's Continental Wrestling Association in Memphis, Tennessee. In 1989, the CWA merged with World Class Championship Wrestling to form United States Wrestling Association. He would remain with the USWA until 1991.

Brian Lee would make an initial appearance at a WCW taping on April 23, 1990 in Marietta, GA when he defeated Bob Cook. He made his debut in World Championship Wrestling's Clash of the Champions XIII on November 20, 1990 losing to The Z-Man.

In November 1991 he returned to the promotion, this time teaming with Chris Sullivan. The duo were defeated by the combination of Diamond Dallas Page and The Diamond Studd Scott Hall in a match that would air on the December 7th edition of World Championship Wrestling.

He appeared in Smoky Mountain Wrestling (SMW) from 1992 until 1995 as "Prime Time" Brian Lee. Lee was a two-time SMW Heavyweight Champion and twice won the SMW Tag Team Championship with partner Chris Candido. Lee was the first-ever SMW Heavyweight Champion, and was also the first Wrestler to ever be managed by Tammy Sytch.

In 1994, he briefly joined the World Wrestling Federation to perform as an impostor version of The Undertaker. "The Million Dollar Man" Ted DiBiase, who originally introduced The Undertaker into the WWF at Survivor Series 1990, claimed to have found The Undertaker, who disappeared after losing a casket match to Yokozuna at the 1994 Royal Rumble. Shortly after this, Lee began appearing dressed as The Undertaker. DiBiase claimed that he had convinced The Undertaker to come back with his vast amounts of money and made him a member of his Million Dollar Corporation, with his powers now derived from DiBiase's riches instead of the urn that he or his manager, Paul Bearer, toted with him to the ring. For several weeks, Lee wrestled matches as The Undertaker while Bearer "made contact" with the real Undertaker and promised to produce him at SummerSlam in August 1994. At the event, Lee's impostor Undertaker faced off against the actual Undertaker and was defeated. After the match, DiBiase fled from ringside while The Undertaker rolled the impostor into a casket that was taken away. Although the idea was for Lee to continue portraying the impostor Undertaker for some time afterward and to have more matches against the actual Undertaker, the WWF dropped the story after SummerSlam.

Lee appeared in the Bollywood film Khiladiyon Ka Khiladi under "The Undertaker" name in 1996.

In 1997, Lee returned to the WWF as "Chainz", a member of the biker faction Disciples of Apocalypse (or DOA) along with leader Crush and his cousins, the Harris Brothers, who were renamed Skull and 8-Ball. The foursome feuded with Los Boricuas, the Nation of Domination, and the Truth Commission during the WWF's "Gang Warz" storyline. Lee remained in the WWF until the summer of 1998 when he was released once again.

After several years out of the spotlight, Lee debuted in Total Nonstop Action Wrestling in 2002, teaming with Slash as the Disciples of The New Church under the leadership of manager Father James Mitchell. On November 13, Lee and Slash won the NWA World Tag Team Championship when they defeated America's Most Wanted ("Cowboy" James Storm and "Wildcat" Chris Harris), thereby ending their undefeated streak. They later lost the titles back to AMW on January 8, 2003.