“I swear to you, we would be on the phone late at night, after like an hour or two, and (Garry) would mention that. ‘I think my phone’s being tapped,’” remembers comic Kevin Nealon. 

“Because you hear clicking. Garry had that crazy side to him too, a little paranoid and neurotic. And I would just roll my eyes and think, Well, okay. Not likely but okay. He seemed very paranoid about a lot of things at that point. But it did turn out to be true.”

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Garry’s phone was actually bugged? Who would wiretap Larry Sanders?

As it turns out, it was someone working on behalf of his old friend and manager, Brad Grey (of the famous and ultrapowerful comedy management factory, Brillstein-Grey). Not that Grey was convicted of anything.

But back to the beginning.

Shandling and Grey basically started in the business together. Their stars rose together, through It’s Garry Shandling’s Show into the genre-busting HBO comedy The Larry Sanders Show. The two men were best friends until they weren’t.

Like all crumbling relationships, there were hundreds of small problems along the way, but a tipping point was when Shandling realized Grey had built a bigger house than his. Real estate envy? Sure, but Garry had the sneaking suspicion that his own success built Grey’s estate.

Shandling’s lawyers reached out to Grey’s group, asking to see the contracts Garry had signed. No response. “And so Garry went and asked,” says Garry’s friend and author, Gavin De Becker. “And the response from Brad was “You don’t want to ask this question.” 

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What Shandling eventually discovered was a) Grey owned 50% of The Larry Sanders Show; b) he took a percentage of Garry’s money as his manager; and c) as a producer of the show, Grey also took producing fees. A triple scoop. On top of that, Grey was luring Sanders writers to create new comedies.  Bottom line?  Grey was making more from Garry’s show than Garry.

“Garry needed an Artie,” says De Becker.  “Instead, he had Brad Grey.”

Shandling filed a $100 million lawsuit against Grey, an act friends felt was as much about expressing his feelings of betrayal as it was trying to make the finances right. 

And somewhere around that time, Grey hired Anthony Pellicano, private investigator to the stars -- or the stars’ very rich handlers.  And when Pellicano was indicted for wire-tapping (not just Shandling but several others), Shandling took the witness stand.

During his testimony, Shandling alleged that as a result of inquiring about those contracts and filing the suit, “Brad Grey threatened me one night to make my life miserable.”  He also claimed on the stand that Grey, with Pellicano’s help, was also planting false stories in the media.

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Pellicano was eventually convicted.  Among other things, he was found guilty of bribing police officers and other officials to run database searches on Shandling, presumably for anything incriminating for the press smear campaign. He served time in the pen from 2008 until his parole in 2019. Grey was never charged.

What happened affected (Garry) on a cellular level,” says journalist Anita Busch. “It hurt him physically, it hurt him mentally, it hurt his confidence, it hurt him spiritually.”

On top of it all, says actor and friend David Duchovney, Shandling was heartbroken.

If any good came of all the legal troubles, it was that Garry’s lawsuit changed the business. “People certainly recognized that you cannot be somebody’s manager and the studio at the same time,” says DeBecker. “And that’s really what the legacy of the case is.”

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