Remembering Garry Shandling’s Classic Interview With Charlie Rose

The world lost a generational talent and one of the good guys with the passing of Garry Shandling at the age of 66 this week. To many, the comedian was more than just a performer or entertainer, he was someone who had “it” figured out. And by “it” I mean everything and nothing. Garry Shandling was an honest man. Someone that, from his own description, “believed in truth and how people should treat each other.” At face value, Garry Shandling seemed like a weirdo – an insecure beta male archetype that would get as many laughs out of a concerned look to the camera as his punchlines. He started his career writing for Sanford and Son briefly after finding himself on the West Coast, but he soon realized that despite his quick success, he wasn’t “burned out at 25,” he was bored. His honesty with himself never waned, and it was an inspiration and guiding light to comedians everywhere.

After leaving the writing life, and despite never stepping foot on stage, he decided to do stand up because “you have to be brave enough to fail.” His success in stand up led to Shandling being one of the biggest comedic stars of the ’80s and ’90s, but he never lost his sense of self, and he never forgot about honesty. He was always one of the most generous and interesting people in the business, because he believed in his value system and he rejected the notion of selfishness.

In this 1998 interview with Charlie Rose, Garry has just wrapped on The Larry Sanders Show, and was preparing to release Hurly Burly. His star couldn’t be brighter, and he comes off as a guru of ego navigation. A plethora of young and upcoming comedic legends like Jon Stewart, Bob Odenkirk, and Judd Apatow have all said that he was an important part of their formative years in comedy, and by sucking them into his orbit, he made them seek the truth in comedy and life. (Even if it was possibly in a facetious way with Ricky Gervais.)

Here are just a few of the nuggets of wisdom that Garry shares with Charlie.

Talent is becoming one with who you are. Honesty honesty in the moment. I don’t know if I entertain or it’s an insecure defense mechanism. But it’s also being honest.

Perfectionism may come from fear of being rejected. But when I see that something can be better I ask myself if I’m being too tough.
The only thing stranger than being on TV every night is wanting to be on TV every night

It turned out the world I thought would turn living in the 60’s turned out the opposite

And when discussing his depleting hair, he made the best and most important observation a man going through that torture can hear:

Hair’s not important… It comes down to what kind of hair you have inside.

We are all Bill Haverchuck from Freaks and Geeks, and Garry will forever make us laugh with a grilled cheese sandwich in our mouth.