All the Ways Garry Shandling Was Impossible on ‘The Larry Sanders Show'

This week marks the 25-year anniversary of the end of The Larry Sanders Show, a groundbreaking HBO series that mined comedy gold from the behind-the-scenes drama of its titular late-night show within a show. Today, we got to hear the behind-the-scenes drama behind the behind-the-scenes drama.

The Washington Post recently reached out to the remaining stars and writers of The Larry Sanders Show to talk shop and smack about their old boss, the late, great Garry Shandling. As it turns out, the TV giant behind the semi/mostly-autobiographical sitcom about a neurotic, petty and self-centered late-night host could be a neurotic, petty and self-centered showrunner. 

The full piece covers stories told by everyone involved in the making of The Larry Sanders Show who still holds a place in their heart for the series that changed how comedy was made on TV — among others, Jeffrey Tambor and Judd Apatow expressed their deep admiration for Shandling, as well as the deep frustrations that working with the man could give them. But of all the stories that paint Shandling as a complicated, passionate and deeply truthful TV virtuoso, one thing is clear — auditioning for him was a nightmare.

Tambor, who played the titular host’s sidekick and announcer Hank Kingsley, recalled the dedication he had to show to earn Shandling’s approval. “I was so amped up for the audition that I left my house about two hours early,” he explained. “In the scene, Larry tries to leave the room, and I moved an entire couch to stop him; I remember Garry glancing at the casting director, Francine Maisler. I knew that was a good thing.”

Penny Johnson Jerald, who played Sanders’ loyal assistant Beverly Barnes, recalled Shandling’s blasé demeanor toward auditioning actors, saying, “As we’re about to start my audition, the phone rings. And rings. I said, ‘I’m sorry, are you going to answer that?’ Garry said no. The phone stops, so I begin. But it rings again, so I answer it. ‘Hello, Garry Shandling’s office. How can I help you? This is my audition.’”

Kids in the Hall comic Scott Thompson, who played Hank’s assistant Brian in the latter half of the series, was fortunate enough to avoid the audition process entirely when Shandling pitched him on the project. “There was no audition,” said Thompson. “Garry was a fan of Kids in the Hall and had probably seen me on Conan. He wanted the character to be gay. I said, ‘Then I have a trade: My character also has to be Canadian.’ Garry said, ‘That’s a bit too much. Nobody’s going to buy that, a Canadian character on television in America.’”

The process for writers to land a job on the show was notoriously difficult, as Shandling was known as one of the most demanding head writers in show business. Alex Gregory and Peter Huyck, the creators of White House Plumbers who briefly served in the Larry Sanders writers’ room, recall being warned by Apatow about the interview they were to have with Shandling at his house. “When you arrive at Garry’s house, there’ll be a famous person. You’ll have to wait while they talk. And at some point, Garry will take a phone call and may even talk about you on the call,” Apatow informed them.

Sure enough, when they arrived at the house, Shandling greeted them by pretending to reject them, then sent them outside. “We go to the backyard, and David Duchovny is sitting there, and we have to wait. And then Garry took a call and talked about us. Just as Judd predicted,” Gregory recalled.

Among the responders to the Post’s inquiries for Shandling stories, Apatow had perhaps the most thoughtful and tragic insights into the man’s mind. “Garry’s philosophy was about trying not to take things so seriously, treating people well and not letting your ego drive your life,” Apatow said, “but those were the things he really struggled with. Garry was satirizing issues that he had.”

“People worked really hard, and a lot did amazing work for a long time and left feeling unappreciated,” Apatow lamented. “I felt sad when they left with a bad feeling, and I felt for Garry, because I could see how much pain he was in. After the show ended, he was much sweeter and more open.”