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Besides Gilda, another key figure in the book is Garry Shandling, with whom you had a falling out. Did writing this book to help give some closure?

To a degree. When he died, I was shocked. We were well on our way to reconciliation. When Judd Apatow called and asked if I wanted to speak at his memorial, Robin and I flew out there for it. That was a catharsis delivering the eulogy. We all recited jokes that Garry had done. There was something communal telling Garry jokes.

What was your working relationship like with Billy Crystal on 700 Sundays?

My role was very much to serve Billy—it’s his life and he’s the one who’s up there. It was also to put words into the mouths of his family members, who I never met. But it’s not like I’m from Venus. We’re both Jews; we’re both from Long Island. It’s not that far from me. I was also writing about my family. That was fun not only to hear those laughs but to dig into my own past. It was a way of reconnecting with old memories, bygone people, and bring them back to life.

As a collaborator, what was your process in navigating that show’s more dramatic and emotional moments, and deciding when and where not to go for a laugh?

I remember we had a discussion about the wake after his father died. I asked him, “You were 15. You had a fight with your dad. He left the house and dropped dead at the bowling alley. In your 15-year-old brain, did you think you were responsible?” It was an honest moment that had to be acknowledged. Whereas, and this is such a weird thing to say, but in other places, I’d say, “We need a laugh at your dad’s funeral. We’ve been too real and too emotional for too long, let’s break it up.”

I learned that years ago in my own speaking engagements when I talk about Gilda’s cancer. She was my platonic friend. We were married to other people, but there was always that little flame. When she got sick, my role was to make her laugh. When it started getting the best of her, I went to give blood at Cedars-Sinai. I got on the gurney, and the nurse gave me a pad and pen, and said that Gilda liked to know whose blood she was getting, and to write something nice. I wrote, “Dear Gilda, I knew I’d get some fluid of mine into you one way or another.” That gets a monster laugh every time I do it, because I’ve just gone a minute telling about my friend having ovarian cancer. It’s an instinct you have in the rhythm of things.

You also collaborated with Martin Short on his one-man show, Fame Becomes Me. I have never heard a negative word about him. Let’s get some dirt.

Look how many things he does so well. It’s unbelievable. If you ask Marty what he did last night, he’ll tell you whose dinner party he went to, and you feel like you were there because he impersonates everyone at the table. As a human being, he’s generous, he’s lovable. I don’t know anyone who doesn’t love him.

You are very gracious in the book to the comedians and writers who served as your mentors. I imagine you’re in that position now, where young comedy writers come to you for advice. What topic do you get the most questions about?

Rejection is a huge one. If you write something, and you believe in it, it doesn’t mean you’re a bad writer if it’s not accepted. It doesn’t mean they’re rejecting your life. Rob Reiner taught me that years ago, but it took years to sink in. After North, when he looks at a review, he detaches himself emotionally and looks for a phrase or a sentence that might be good for an ad. I haven’t evolved to that point.

At the same time, this book is getting wonderful reviews. It seems to be touching a nerve, and that’s great. You do what you do. There’s a certain moxie and bravery you have when you write something and you share it with other people. We all hold our breath. We all want positive feedback.

This interview has been edited and condensed for clarity.

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