Why did you decide to write a book about other people’s success stories?
At some point in your life, don’t you sort of wonder if you’re in the right space? Sometimes I feel like decisions just happen to you. I wanted to meet some people who had their hands on the steering wheel.
When have you had moments like that?
I’m still having them. I actually think I’m supposed to be with kids somehow. I thought I would have kids, but circumstances happen, illness and divorce, and all of a sudden you’re sitting here going, What happened? I know it’s not in the cards in this moment, but it’s something I’m looking toward, whether it’s teaching or opening a camp. That being said, I did hard-news journalism for a long time, and I don’t really think it was ever the perfect fit for me. My heart broke a lot when I was covering things.
Did it feel like a better fit when you started doing Today?
With Kathie Lee [Gifford]? You mean the drinking and laughing? Yeah! When she showed up, the world changed for me. She’s electric, and she doesn’t care–there’s such a freedom. I’m sitting next to her, and sometimes it’s like the grenade’s exploding next to you, like it’s collateral damage. Am I fired too? O.K., bye! You don’t know, but it’s such fun that you don’t care.
Whose idea was it to drink wine on the show?
Chelsea Handler showed up one day, and she had that book Are You There, Vodka? It’s Me, Chelsea. So as a gag, we said, “Let’s make drinks.” And then a few days later, Brooke Shields came on and said, “Where’s mine?” Then it was like a wave. We started naming the days: Funday Monday, Boozeday Tuesday, Winesday Wednesday. I don’t think the top brass knew what we were doing for a while, because nobody watched us. They were busy! And then one day, they were like, “Are they drinking?” We were like, “Oh, we’ve been doing that for months. TIME called us the Happy Hour.”
How much wine is too much wine?
On the show, we sip, because we don’t want to get sloppy and disgusting–it would be bad, especially for the last guest on the show. When you stop being happy, it’s time to stop.
What advice would you give to young working women?
Do the jobs that no one wants to do. And don’t do what you’re asked–do more than what you’re asked.
A lot of people in your book are faith-driven. What role does faith play in your life?
It matters. I remember one of the most poignant moments for me was when I was diagnosed with cancer, and I walked by the guest bedroom in my apartment, and Karen, my best friend, was on her knees. I still can picture her sitting there, unaware of me, and I thought to myself, Prayer is power, man, it is powerful.
Who’s been your favorite actor to portray you on Saturday Night Live?
I don’t know, because they kept getting fired! I think it was Jenny Slate. I just know I got pushed around by Kristen Wiig, no matter who played me. I thought it was exactly like watching our show. Kathie goes, “That’s nothing like our show!” I go, “They’re not even changing the dialogue. You said that to me, and I said that to you!”
You’ve talked about pubic hair and peeing your pants and kissed Regis Philbin on air. Any regrets?
Of those three? Yes, yes and yes! I better not say yes to kissing Regis–let’s just do the first two.
This appears in the January 18, 2016 issue of TIME.