Chainz would make an initial appearance at a World Championship Wrestling (WCW) taping on April 23, 1990 in Marietta, Georgia 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 in a match that would air on the December 7 edition of World Championship Wrestling.
He made his first appearance for the World Wrestling Federation during a Wrestling Challenge show, losing to Kevin Von Erich in 1991. He then wrestled in a dark match against Chris Walker the following day at the 1991 pay-per-view event This Tuesday in Texas. On October 28, 1992, he received another tryout at a Wrestling Challenge taping in Louisville, Kentucky, and was defeated by Jim Powers.
In 1994, he briefly returned to 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, Chainz 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, he 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, Chainz'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.
By early 1996, he began competing in Extreme Championship Wrestling. During this period, he went by the nicknames "Prime Time" Brian Lee, Bulldozer and later Killdozer and was allied with Raven as a hired bodyguard for his stable.
Lee and Tommy Dreamer then got involved in a very violent and personal feud, which began through Dreamer's feud with Raven. At the ECW event Fight The Power on June 1, during a six-man tag match, Brian Lee chokeslammed Dreamer from the ECW balcony through three stacked tables, then pinned Dreamer for the win.
On June 22, at Hardcore Heaven, after losing a singles match to Dreamer after Dreamer's valet Beulah McGillicutty got involved, Lee again chokeslammed Dreamer off a balcony through three tables. At Heat Wave, during a three on three "Rage in the Cage" tag team cage match, Lee again chokeslammed Dreamer, this time from the top of the cage through three tables set up on the outside by Raven's henchmen. On October 5, at Ultimate Jeopardy during a tag match also involving Sandman and Stevie Richards, Lee once again chokeslammed Dreamer from the ECW balcony, this time through four tables set up below.
At several house shows, Lee and Dreamer had Falls Count Anywhere matches which resulted in the two men brawling in moving traffic outside the building. The feud culminated at ECW's High Incident event. During his Scaffold Match with Dreamer, Lee took a major bump from the scaffolding high above the ring through a series of tables stacked up inside the ring.
At November to Remember, the main event was a tag match pitting Dreamer with Terry Funk against Shane Douglas and Lee. From here, Lee began a feud with Funk, which lasted until 1997. Lee also became a part of the revived Triple Threat stable with Douglas and Chris Candido, while a masked man who was hinted at to be Rick Rude began stalking Douglas. At ECW's Barely Legal, it was revealed that the masked man was Lee himself. He attacked Shane Douglas and kissed Francine before leaving the ring with Rick Rude. Lee left ECW soon after.
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 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. Chainz remained in the WWF until the summer of 1998. His last match in the company was on June 15, 1998, which was a loss to Val Venis. After this match, he was released from the company once again.