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In 1984, Grey met talent manager Bernie Brillstein in San Francisco, California, at a television convention. Having convinced Brillstein that he could deliver fresh talent, he was taken on as a partner, and the Bernie Brillstein Company was rechristened Brillstein-Grey Entertainment. Grey began producing for television in 1986 with the Showtime hit, It's Garry Shandling's Show. In the late 1990s, Shandling sued Grey for breach of duties and related claims. Shandling complained that his TV show lost its best writers and producers when Brad Grey got them deals to do other projects, and that Grey commissioned these other deals, while Shandling did not benefit from them. Grey denied the allegations and countersued, saying the comedian breached his contract on The Larry Sanders Show by failing to produce some episodes and indiscriminately dismissing writers, among other actions. Both suits were settled, avoiding a trial. Shandling did testify about Grey during the 2008 trial of private investigator Anthony Pellicano, who worked on Grey's defense team. The value of the settlement to Shandling was later disputed by attorneys as being either $4 million or $10 million.

In 1996, Brillstein sold his shares of the Brillstein-Grey company to Grey, giving Grey full rein over operations; the company's television unit was subsequently rechristened "Brad Grey Television". Grey produced shows such as Emmy Award-winning The Sopranos and The Wayne Brady Show. Other shows developed in the 1990s under the Brillstein-Grey banner included Good Sports, The Larry Sanders Show, Mr. Show, Real Time with Bill Maher, NewsRadio, The Steve Harvey Show, and Just Shoot Me! Grey also ventured into film by producing the Adam Sandler hit Happy Gilmore.

In 1996, actress Linda Doucett alleged that Grey and Shandling fired her from The Larry Sanders Show after her personal relationship with Shandling ended. Doucett reportedly received a $1 million settlement in this matter in 1997.

In July 2000 - on the day of Scary Movie's opening - Grey and Brillstein-Grey were sued by Bo Zenga and his Boz Productions in what became known as the 'Scary' suit. Zenga, at the time an unknown bit-part actor, "claimed he had an oral agreement with Grey's management firm Brillstein-Grey Entertainment, giving him equal profits on the film". Scary Movie went on to make $278m worldwide.

The pre-trial discovery process "revealed that major parts of Zenga's resume were fabricated. Brillstein-Grey said in a court filing that Zenga presented himself as a successful investment banker who became a prize-winning screenwriter to satisfy his creative urges." "Far from being a successful investment banker, Zenga once filed for personal bankruptcy" and "according to court papers, the only writing award he won was in a phony contest he set up himself." After denying under oath that he knew who owned the company that ran the contest, Bo Zenga recanted a day later, admitting his ownership of the company and "saying he had been 'overmedicated.'" When questioned about "an accusation from his former business partner that he coerced her to lie for him," Zenga "in a highly unusual move for a plaintiff in a film-profits case — asserted his Fifth Amendment right not to answer hundreds of questions." Zenga's suit was thrown out of court for lack of evidence. L.A. Superior Court Judge Robert O'Brien "noted it was only the second time in all his years on the bench that he had granted a non-suit and taken a case away from a jury."

In 2002, Grey formed Plan B with Brad Pitt and Jennifer Aniston, with a first-look deal at Warner Bros. The company produced two films for Warner Bros: Tim Burton's Charlie and the Chocolate Factory with Johnny Depp, and Martin Scorsese's The Departed, starring Leonardo DiCaprio, Matt Damon, and Jack Nicholson. After Pitt and Aniston separated, Grey and Pitt moved the company to Paramount Pictures in 2005.

In May 2006, Zenga "filed a new suit against Grey personally," in which he charged Grey with using notorious private investigator Anthony Pellicano to illegally wiretap and conduct illegal background checks on Zenga during the original case. Grey denied any knowledge, testifying that "his dealings with Pellicano 'all came through Bert Fields' and that 'in every instance' Grey had never been given updates on the investigations by Pellicano." The suit was "dismissed, due to Zenga having lied and to statute of limitations issues." Zenga's appeal continued after Grey's death until being dismissed in December 2017.