Take a walk through Judd Apatow’s office, like I did, and you’ll be reminded of all the successful projects he’s helped create over the years: Anchorman, Bridesmaids, Superbad, The 40-Year-Old Virgin. I joined him there to discuss his new visual memoir, Comedy Nerd: A Lifelong Obsession in Stories and Pictures. As I learn throughout our conversation, Judd’s propulsion to create isn’t to prove that he’s one of the funniest guys in the biz; it’s to figure out if he has anything to say in the first place, to work out what’s in his head. It’s something I relate to as a writer, and it’s a big part of the new book, as he documents everything he’s collected and concocted over the years and tries to make sense of this life that he’s made. As we reflect, we also talk about our most scathing reviews, why we can’t Google ourselves, and how Judd’s documentary on our mutual friend, Garry Shandling, helped cement his subject’s legacy.

Fail Better is now on YouTube! Watch this episode here.

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