THR's Sherry Lansing Leadership Award honoree confesses to a fellow late-night pioneer her fear of bombing onstage (his response: "It's like I have a twin") as two comedy greats talk Trump's feud with Alec Baldwin ("dignity of a seventh-grader"), the "endless anxiety" of parenting and why TV is "better than movies."

There was a certain nervousness in the air as a handful of publicists and managers — along with this reporter and his two digital recorders — gathered at Manhattan's Circo restaurant Nov. 21 to witness the reunion of two comedy giants: Tina Fey and David Letterman.

Letterman was making one of his rare forays out of retirement to conduct an in-depth interview with Fey, the 46-year-old creator and star of 30 Rock and executive producer of Unbreakable Kimmy Schmidt. One of the most iconic women in entertainment, whose films include 2004's Mean Girls and 2010's Date Night, Fey (who has an overall deal with Universal) wrote the best-selling memoir Bossypants, was the first female head writer on Saturday Night Live and may have changed the course of American politics with her deadly impersonation of Sarah Palin.

In recognition of her professional leadership and work on behalf of women in Hollywood, especially in comedy, Fey is this year's recipient of the Sherry Lansing Leadership Award — an honor previously given to such luminaries as Oprah Winfrey, Jane Fonda and Shonda Rhimes — which she'll receive Dec. 7 at THR's annual Power 100 breakfast in Los Angeles.

While Letterman, 69, came exquisitely prepared for the interview — armed with a sheaf of handwritten notes — those of us who sat at a nearby table, just out of hearing distance, were unsure what would follow. A few minutes after he arrived (tall, ramrod-straight and patriarchal, with a full beard and dressed in a T-shirt despite the chill outside), Fey walked in with a hint of the same nervous anticipation the rest of us were feeling.

The Emmy-laden (nine in all) star and comedy creator, who is developing a Mean Girls musical and whose new comedy series, Great News, debuts in 2017 on NBC, greeted everyone warmly, then joined Letterman at a corner table to talk — and talk and talk. When their time was up, Letterman decided he wasn't finished and went back for 15 minutes more as these two whip-smart perfectionists volleyed back and forth about Trump, parenting, comedy and Hollywood.

David Letterman How are you doing?

Tina Fey OK. How are you?

Letterman I'm full of apprehension and self-loathing.

Fey More than usual? More than a baseline? Or, "I feel very, very anxious post-election"?

Letterman I'm feeling anxious. I find, since I don't have a show anymore, I can't stop talking, and this is not supposed to be about me. So what do you think is the No. 1 struggle of humanity now? This is an easy one.

Fey Let's talk about that. Because I think if you were on TV, you'd be helping us with this, Dave: How are we going to proceed with any kind of dignity in an increasingly ugly world? And I actually was thinking — because I've got to write something for when I get the award — to use Sherry Lansing as an inspiration because she was a lady who worked in a very, very ugly business and always managed to be quite dignified. But in a world where the president makes fun of handicapped people and fat people, how do we proceed with dignity? I want to tell people, "If you do two things this year, watch Idiocracy by Mike Judge and read [Nazi filmmaker] Leni Riefenstahl's 800-page autobiography [Leni Riefenstahl: A Memoir] and then call it a year."

Letterman Wait a minute. Tell me about Leni Riefenstahl.

Fey She grew up in Germany. She was in many ways a brilliant pioneer. She pioneered sports photography as we know it. She's the one who had the idea to dig a trench next to the track for the Olympics and put a camera on a dolly. But she also rolled with the punches and said, "Well, he's the fuhrer. He's my president. I'll make films for him." She did some terrible, terrible things. And I remember reading [her book] 20 years ago, thinking, "This is a real lesson, to be an artist who doesn't roll with what your leader is doing just because he's your leader."

Letterman My impression of this woman is that she was the sister of Satan.

Fey: She was in many ways. But what she claimed in the book was, "He was the president, so what was I supposed to do?" And I feel a lot of people are going to start rolling that way.

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Letterman Now here's something I think about with my son: I know firsthand that the behavior of men is often questionable. Maybe even immoral, maybe even illegal. I have had to learn how to behave with women because nobody ever taught me. I learned it from my peers, and that's not always a topic that peers are good at passing on. I can tell you that the world is full of jerky men.

Fey Yes.

Letterman And parenting is a nonstop, endless horizon of anxiety. Is this a weight that you have to carry: "How will my girls be treated? Will they be able to take care of themselves?"

Fey I worry, [but] I have confidence that they are both strong enough to fight back, and I think they will feel empowered to call attention to any wrongdoing in their lives.

Letterman You've got two, right?

Fey Eleven and 5. One's in fifth grade, one's still in preschool. And so everybody's up by 6:30, out the door to the bus. I take the dog out and run to the bus, come back, take the other one to school.

Letterman My son, Harry [who's 13], wanted to know if I was taking him to school this morning, and I said: "No. Geez, God, I'm not getting up that early. I have to talk to Tina Fey." And there was a double take, like, "Stay away from the really important people." I thought, this is very cool: My son knows you and knows I should leave you alone.

Fey He knows about the restraining order?

Letterman I'm so old, and I just love kids now. They used to scare me. I didn't want them because I thought, "I have to focus on this ridiculous career, and kids would get in the way." And now I realize that was a huge mistake.

Fey No, they augment your life and your perspective. And they wear you out. There's a Stephen Sondheim song, "Being Alive." It's about how people you love just wear you out and irritate you and sit in your chair and make you lose sleep. But it's what life is.

Letterman With me and my son, if it was a stranger, there'd be a fistfight. But because it's my son, the next thing you know, we're having meatballs. Is your 11-year-old a good student?

Fey So far. She's a kid who just does her homework right away.

Letterman Well, that was you, too, wasn't it?

Fey I think so. Around high school, it got harder. I can remember the feeling of, "Oh, it's Sunday," and you hear the 60 Minutes theme and start to have a panic attack because you didn't do your homework. But she's not like that — so far.

Letterman So, this award [you're getting]. When I was in California, it was all about Sherry Lansing. You've actually worked with her, right?

Fey Once. The one time I've written a movie, Mean Girls, Sherry was the head of Paramount, and she was very enthusiastic, and at the time, I didn't realize how rare this was. I had never written a movie before. She never took that screenplay away and said, "Now let's give a two-week pass to some guys that we'll pay $500,000 to fix it." She just let me keep plugging at it.

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Letterman Do you like getting awards?

Fey This one makes me a little nervous. Have I really done enough to warrant this? Sometimes I tell myself, "Well, what would a guy do? He'd take it." They wanted to give me that Mark Twain Prize [for humor] in 2009, and I said, "I don't think this is appropriate." And Lorne Michaels said to me, "Just take it while your parents are alive," which is very smart.

Letterman Do your girls have a better awareness [of feminism and opportunity] than they might have had 20 years ago?

Fey It feels like we were on the precipice of things getting pretty good, and now we're in a bit of a throwback moment. I definitely came out of last month feeling misogyny is much more real than two years ago. But the thing I worry about [more] than actual human interaction is the internet. Because that's just despicable: people just being able to be awful to each other without having to be in the same room. It's metastasizing now, thanks to our glorious president-elect who can't muster the dignity of a seventh-grader. It's so easy for people to abuse each other and to abandon all civility.

Letterman But why? I mean, for God's sakes, why?

Fey Because when you're mad, you're just mad about what you see in front of you, and you fire it off and lash out at someone in a way that you would probably not do in the doughnut line at church.

Letterman Wait a minute, there's a doughnut line at church?

Fey My church, there was. They cut those doughnuts into four.

Letterman Thank you, Jesus.

Fey But I could reassemble them, sir. Did you see that my friend Mr. [Alec] Baldwin is in a Twitter feud with our president-elect? [Baldwin responded to Trump's complaints about SNL parodies of him.]

Letterman Good for him.

Fey At one level, it just makes me feel sick for the state of the world because it's so beneath a president, but also my feeling is: "You think you're good at being a jerk on Twitter? You will now face the grandmaster of being a jerk on Twitter."

Letterman Then the president-elect says [to the Hamilton actor who read a statement about diversity to Vice President-elect Mike Pence after a performance], "You owe him an apology."

Fey Immediately, my brain went to Lorne Michaels. I thought, our president-elect is a chump of a manager because don't put yourself in a position where you're asking for something and you're going to be told no. I learned that from Lorne. You're the president. You demanded an apology that you can't get. Bad management skills.

Letterman I've known Lorne Michaels as long as I've been in New York City, and I've always been afraid of him.

Fey Really? He's nothing to be afraid of.

Letterman But how about this guy single-handedly forming the culture of comedy in America? Is that too much to say about him, hyperbolic?

Fey He's deeply influencing it.

Letterman You're friends? You go to him for advice?

Fey Not necessarily like, "What's the blow for the end of Act 2?" But big-picture things of how should I live my life, how to handle this person, jobs to take or not take, ways of managing people.

Letterman Would you want to drive cross-country with him?

Fey Oh, absolutely. Although between the two of us, I don't know that there's a good driver.

Letterman Do you watch any network TV?

Fey Other than SNL and picking up the occasional talk show the next day on the computer — I go to bed so early now; I'm on that kid grind — I don't. I keep trying to figure out how to make one for NBC because there's success to be had if you can figure out a way to make The Big Bang Theory and everyone likes it.

Letterman I read you talking about Unbreakable Kimmy Schmidt, how these are characters you created, therefore you love them. And you want to take care of them. What is that?

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Fey You want them to not say something they wouldn't say or put them in a situation that doesn't feel believable. You have to feel for them to keep making up stories about them for seven years. Otherwise everyone will start to talk the same and the jokes will just be them throwing insults at each other. With Kimmy Schmidt, we made the first season for NBC, and then it ended up being sold to Netflix. We were in that second year going, "Now we're on Netflix, we can do whatever we want." And we made the choice of, "Let's keep making it clean."

Letterman One of the many things I like about you, you've set a course in the right direction for men and women. Do you know about Mitzi Shore?

Fey The lady who ran [The Comedy Store] in L.A., right?

Letterman Mitzi Shore put a lot of people in business. She created a program for women comedians. At the time, we just thought, "Oh, good." But there was some vision there.

Fey My small-town version of Mitzi Shore was Charna Halpern from Chicago, who runs the ImprovOlympic, and she was a scrappy lady. She's the one who put me and Amy Poehler together on a team and said, "You two should be together."

Letterman Is she your best friend? Your best friend in show business?

Fey She's a very dear, dear friend. I have a group of women that I worked with at SNL — Maya Rudolph, Emily Spivey, Paula Pell, Amy Poehler, Ana Gasteyer, Rachel Dratch — and we talk as a group through the computer every single day. Dozens of times a day. And it's very nice. It's something we've come to in our 40s. It was easy when we worked at SNL: You're on top of each other 60 hours a week. So it's nice that we are maintaining this friendship.

Letterman The Golden Globes seemed to me to be really right on the money for the two of you. [Fey and Poehler have co-hosted three times.] Does that represent your core-DNA sense of humor?

Fey It probably does. I was proud of us doing that because we took what we had learned over the years and applied it. I felt we had a good sense of, "hey, don't do too much." No one really wants to see that much. Like, don't put a really long comedy bit near the end. When I watched the Oscars, I was like, "Why is somebody not telling these guys that?" Everyone wants to leave at the end.

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Letterman What was the most recent funny film you saw?

Fey We showed our 5-year-old Little Shop of Horrors the other night, which is very good. Frank Oz directed it, and Rick Moranis is a treasure. Recently? Hmm. I went to vote for the People's Choice Awards online because actors in our show got nominated, and I realized that I hate everything. Every movie. "That was dumb, didn't see it, haven't seen it, hated it." TV might be better than movies. Shh, don't tell anyone.

Letterman Does that go off the record here?

Fey No, I stand by it. TV's better than movies. Everybody knows it. I mean, we act like they're so great, but what was the last great movie you saw?

Letterman I used to see them all the time when I had a show. We had a screening room, and we would see two or three a week.

Fey The last new movie that I saw in the theater was Election, the early Alexander Payne movie with Reese Witherspoon. That was hilarious.

Letterman Where do you go on vacation?

Fey Ohio and Disney World. That's about it. Ohio is where my husband's family is. I'm from Pennsylvania. I like to go to Cape May, New Jersey. And I also have a little house on Fire Island. My neighbor always goes, "Don't tell people. People on Fire Island don't want people to know about that."

Letterman What kind of music do you like?

Fey I definitely think of myself as not a super-cool music person. I'm not a person who knows the latest and newest by any means. So if I have my radio on — it's so old. My Pandora radio will have an Elvis Costello channel and a Loretta Lynn channel. And all the show tunes. That's kind of where I max out. I'm not the coolest. That's the big perk I miss about not being at SNL anymore — hearing the house band every week and the guest every week. Because that would be my only exposure to new music, and just what you want: Give me your top two songs.

Letterman When you were a youngster, SNL was your shining city on the hill?

Fey Once I was big enough to stay up — although somehow I remember Gilda Radner. I'm born in 1970, so I don't know how I'm remembering that firsthand. Jan Hooks, I loved so much. Whenever, as a kid, you get old enough to stay up and watch it for real, that's your sweet spot. And for me that was Phil Hartman, Jan.

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Letterman Oh, Phil Hartman. Holy God. He would come on our show and you could feel the energy radiating off the guy. You're post-[John] Belushi and Dan Aykroyd?

Fey That was just definitive. And then going into my era, Will Ferrell, for sure, one of the best that ever lived, and coming from a really specific place, never mean-spirited, just a very warm place. And in terms of someone who could have been made in a lab to do that show, there's nobody better than Maya Rudolph. She can take things that aren't funny and make them funny. She did a bit this summer, a Melania Trump thing, that I happened to see before Melania had even spoken, and it was just her eating diamonds — Melania Trump's edible diamonds — and I could watch it for three hours.

Letterman Did you ever participate on SNL when something just bombed?

Fey Oh, for sure. I was in a couple of sketches that were pretty bad. If I was in a sketch, that was already a red flag. But that can almost be fun in its own way. Rachel Dratch and I have that relationship, going back to Second City, of just locking eyes while bombing — and it's as close as I'll get to feeling what it's like to jump out of a plane. Just that free-fall of, "Well, this is terrible. But the parachute will probably come out."

Letterman It's an assault on one's dignity, isn't it?

Fey It is. I don't know about you, but I find any little thing I do, if it doesn't go well, I just carry that bomb juice on me for days. I had to do something the other night at a charity thing, and I was promised I didn't have to write any jokes, and every year I forget that when I introduce the band, it takes them two-and-a-half minutes to bring the banjos out and stuff. And so it was like, "I'm here. I have nothing." And I'm dying. And I don't even have the wherewithal to improvise anymore. I just stood there. And then for three days, I was in a bad mood because I bombed.

Letterman This is me. It's like I have a twin. The humiliation of bombing is so much lower than the exhilaration of doing something well.

Fey It's much longer-lasting.

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FROM IMPROV TO TV EMPIRE

Fey’s SNL success led to a path of prolific comedy creation

1. Fey first honed her improv comedy skills at Chicago's Second City, where she met and performed frequently with Amy Poehler.

2. After joining SNL in 1997, she became its first female head writer in '99, moving into the "Weekend Update" anchor chair in 2000.

3. Netflix's Unbreakable Kimmy Schmidt, currently filming its third season, has scored 11 Emmy nominations.

4. David Letterman says he's a fan of Fey's highest-grossing movie, 2010's Date Night, with Steve Carell ($152.3 million worldwide).

5. 30 Rock won 16 Emmys and six Golden Globes — three of each for Alec Baldwin, the boss to Fey's Liz Lemon.

This story first appeared in the 2016 Women in Entertainment Power 100 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.