Alison Stewart: This is All Of It. I'm Alison Stewart, live from the WNYC Studios in SoHo. Thanks for sharing part of your day with us. I'm really grateful that you're here on the show. Today, we'll mark the 250th anniversary of Thomas Paine's revolutionary pamphlet Common Sense with Julie Silverbrook. She's the vice president of civic education at the Constitution Center. We'll also talk to musician Don Was about his new solo album and preview his show at the Blue Note Jazz Club on Monday.

Plus, two conversations with folks nominated for Golden Globe Awards. They're happening this weekend. Tessa Thompson, who is nominated for Hedda, and director Park Chan-wook, who is nominated for his film No Other Choice. That's the plan. Let's get this started with a show about ambition.

[music]

Alison Stewart: Imagine a series of short stories brought to life on a Broadway stage featuring bold-faced named comic actors while the New York funk band Lawrence provides music along the way. That is what you will find at All Out: Comedy About Ambition, and it is ambitious. The sets are by Tony nominee David Korins, and it's directed by Tony winner Alex Timbers, who has four shows running on Broadway. 17 actors are rotating through. Currently on stage, you'll find my next guests in starring Rose, Cecily Strong, and Beck Bennett. It's nice to meet both of you.

Cecily Strong: Hi, nice to meet you.

Beck Bennett: Hi, nice to meet you.

Alison Stewart: Also joining us is the writer of All Out, Simon Rich. Hi, Simon.

Simon Rich: Hey, thanks for having us.

Alison Stewart: All Out: Comedy About Ambition is playing at the Nederlander Theater. You did a version of this, Simon, called All In: Comedy About Love. Why did you want to take on ambition?

Simon Rich: It's just something I've always been gravitated to. Characters who are very ambitious but don't quite pull it off. You'll find a lot of characters in this show that for whatever reason, never quite got the esteem or respect that they hoped for. One characteristic story is from the perspective of Paul Revere's horse, Oatsy, who is the person who Paul Revere rode during his midnight ride, but sadly, his contributions have been lost to time, and he's extremely bitter about it. Those are the characters that I really enjoy writing about.

Alison Stewart: I liked Oatsy personally when I saw it.

Simon Rich: Thank you.

Alison Stewart: How do you describe the show, Beck, when you describe it to people?

[laughter]

Beck Bennett: I go like that first. I say, it's like SNL on Broadway a little bit. It has music. It has these short stories, which are like sketches. It's like a performed reading, where we are. We have the books in front of us. We aren't off-book, but it is fully staged. There's so many things happening. There are these drawings behind us. Lawrence is like this intoxicating energy. It's so fun to be like-- It's like a musical in that sense. We get to enjoy being on stage and reading Simon's words, which are so funny, and we get to feel like we're in a musical with this band all around us. It's really fun.

Alison Stewart: Cecily, how did you get involved with this?

Cecily Strong: I saw All In last year-

Alison Stewart: Oh, okay.

Cecily Strong: -and loved it. This came around, and I jumped at the opportunity. I'm filming another show in Toronto right now, but I was like, "We are carving out time. I'm doing all out. I am going to be a part of it this year. I'm not pregnant anymore." I was lucky enough I got to jump in this year.

Alison Stewart: Congratulations having the baby, by the way.

Cecily Strong: Oh, thank you. [chuckles]

Alison Stewart: How did you get involved, Beck?

Beck Bennett: I got an email from my agents.

Alison Stewart: It's good to open your email.

Cecily Strong: It all starts with an email, folks.

Beck Bennett: I was like--

Cecily Strong: Simon, write that.

Beck Bennett: Yes, write that, Simon. We could put it in the show tonight. I don't know if something-- Well, just type it out.

Cecily Strong: Something improvised, maybe.

Beck Bennett: That would be great. I was at SNL when Simon came back as a writer, when John Mulaney was hosting, because he was writing there with him a lot. That's how I met Simon. I did a short story of Simon's a while ago for Audible. I knew him, and we've worked together before, and I jumped at the opportunity to do it again.

Alison Stewart: Simon, you said of writing that the delete button is your friend, but you can't delete performances. They're up there for people to see. What did you learn from that previous experience with All In that you were able to use in this show?

Simon Rich: I think the thing that's so thrilling about these shows for me is just how elastic it is. Every single comedian is so talented, but also very distinct, and they all bring something completely different to the roles. It's thrilling for me to get to work with such talented performers and to see what interesting directions they take the material. It changes every week, and the fact that it's that dynamic, I think, is really cool.

Alison Stewart: Why did you laugh at that?

Cecily Strong: Oh, because I'm just thinking about even when I've been there. Last week we had Ben Schwartz and Beck, and Ben are so different. It's been fun for me to be next to it on stage, watching. Now it's Jim Gaffigan's last week, who is outrageous and so much fun, makes me laugh so much. Then Mike Birbiglia is coming in, and I'm like, "They're very different energies. I can't wait to see what Mike does." You'll get to see a little bit today. We get this rehearsal.

Beck Bennett: We got to put in rehearsal today right after this.

Alison Stewart: Oh, that's going to be exciting.

Cecily Strong: We got a little mic for Biggs' preview.

Alison Stewart: That's all exciting.

Beck Bennett: Yes, and it's wild. I did my first show on Tuesday, and today is Friday. It feels like a week has gone by. That first show, I had only done it once with Cecily and Wayne. I hadn't even done it with Jim. Now I'm the expert after three shows because it'll just be me, Mike, and the other understudies.

Alison Stewart: You took over for Ben Schwartz, right?

Beck Bennett: Yes.

Alison Stewart: Did you see the show with him in it?

Beck Bennett: I did, and he was amazing. I love Ben. I know Ben. It was interesting seeing the show and being like, "Okay, I'm doing that, but do something different." What he's doing works so well. Figure that out. Do that, but different. Do it your way.

Alison Stewart: As a new kid on the block, what did you have to learn?

Beck Bennett: We have these teleprompters out there. It's like, because we aren't off book, but we also have the books in our laps, I had to learn the dance of watching the other performers and staying engaged with what's happening. Also, keeping my place in my book in case anything does happen with the teleprompters, but also keeping my place on the teleprompters out there-

Alison Stewart: Oh, interesting.

Beck Bennett: -and sort of like that, and not losing my place, just being engaged, because it's very different being fully on cards. At SNL, is one thing. You can read everything, but with this, you're going back and forth, and you don't want to lose your place. It's easier almost to be fully on cards and fully memorized, but to go back and forth between the two is a little bit of a dance that I had to learn.

Alison Stewart: How did you learn to use the book, Cecily?

Cecily Strong: I think, Alex, in our rehearsal, gave a great note that was if we're talking to each other, use the book more and then speaking out. Even after a week and a half, this old veteran here, I feel like I'm very comfortable with it now. You really do start to know it, which frees us up to be a little bit looser. It's been different every night. It's very exciting. It's what live theater is supposed to be.

Simon Rich: I've always wanted to do something that was like SNL, that had that rapid immediacy, but took place much, much earlier at night.

Beck Bennett: The experience is like SNL, but it's so much more decent and just more relaxed and just enjoyable.

Cecily Strong: I can walk in heels a little easier. I'm less of a baby deer when it's not 1:00 AM.

Alison Stewart: We're talking about the show All Out: Comedy About Ambition playing at the Nederlander Theater. My guests are actors Cecily Strong and Beck Bennett, as well as writer Simon Rich. When did you write these stories, Simon?

Simon Rich: These stories, the earliest ones, it's hard to believe, are about 20 years old.

Alison Stewart: Oh, really?

Simon Rich: The most recent ones are from around this year or last year. Doing these compilation shows all in and all out, it's really fun to revisit past material. Much of it does not hold up, I found, but you can just delete those. It's exciting to throw some in that still work that are, at this point, a couple of decades old.

Alison Stewart: For the essay question, do you have to be ambitious to make it in New York City?

Simon Rich: I guess, I don't know. None of these characters really do make it.

[laughter]

Simon Rich: They certainly try. For better and for worse.

Alison Stewart: Beck and Cecily, when you're thinking about these stories, they're fable-like, in many ways. What did you think about ambition when you heard these stories? Did it change the way you thought about it? Did you think about it differently before? What do you think?

Beck Bennett: Go ahead.

Cecily Strong: I was just going to speak specifically. Simon writes this piece from New York City's perspective. I've had so many people, and I get to read it, which is very nice. Thank you, Simon. I don't know if I've told you that. I get all these great comments from people afterward, from young to old, to say, like, it moved them, it made them cry. It's just everybody can see themselves in it. I think that it's so nice ending with that piece because all of us, especially living in New York, I do think you have to be ambitious.

It's all about, like, "What do you put up with in order to be in New York?" This is the life that you're choosing. A lot of times, for us, anyways, it's to be in this business of the arts, and it's everything that the city throws at you. I had a friend see the show two days ago, and he was like, "You got New York right. Not many people do, and you guys, you got it right."

Alison Stewart: It was interesting when you play New York. You talk about how well people take advantage of New York, we'll just say in certain ways. How do you get into the mindset of New York as you're getting ready to play that role, because you are closing out the show?

Cecily Strong: I like to think of it going in like it's supervillain and then the supervillain who's also impressed by their adversary, which are the young people who make it in New York.

Alison Stewart: I kept thinking of that New York Times piece, or was it New York magazine, about the West Village girls?

Cecily Strong: Oh, yes.

Alison Stewart: When you were doing that, I kept thinking about it the whole time. Beck, you take on a fresh take on the emperor's new clothes, and you play the emperor. What's one piece of the story that's really fun for you?

Beck Bennett: Without fully giving it away, there's a real turn. There's a real setup one way. Then I get to make the audience think I'm going a direction, and then I switch directions and build it like being emotionally invested in that, how genuine I am about how I've changed. Then making that turn after that is really fun. I get to really talk from the heart a little bit, and then I get to be gross.

[laughter]

Cecily Strong: Simon's got very good with those turns. It's like gross and sweet.

Beck Bennett: You really get to build up that.

Cecily Strong: [unintelligible 00:11:59] that.

Alison Stewart: How do you find that balance between gross and sweet, Simon?

Simon Rich: I've always been attracted to unusual juxtapositions. There's a lot of weird characters in the show, as you would expect. There's superheroes, there's monkeys, there's time travelers, there's talking horses. I think at the end of the day, they're weirdly, very emotionally grounded autobiographical stories for me and hopefully for the performers as well. We talked about SNL, and a lot of these stories I wrote either while I was writing for SNL or about my experiences at SNL, trying to make it at that show. I hope that people will find the show funny, of course, but also, emotionally honest, and that they'll relate to these characters, as weird as they are, as much as I do.

Beck Bennett: Just to answer your question a little bit from earlier, one of the things I love about the show, as far as I think about ambition and everything, I didn't know what the stories were going to be, but getting into it, it's so relatable how when you try to achieve something in life, even if you achieve what you're going for, there's still a way to be disappointed and feel like you haven't made it.

You look at people, and you're like, "Wow, look how incredible they are." They probably are dealing with the same thing we're all dealing with, and being disappointed and frustrated and looking at other people, how other people are a step ahead of them, even though they've accomplished so much. He does that in such a relatable way through these stories.

Alison Stewart: We're talking about the show All Out: Comedy About Ambition. My guests are actor Cecily Strong and Beck Bennett, as well as writer Simon Rich. Cecily, how does the audience change the way you perform tonight?

Cecily Strong: This is across the board, I think, for every show I've ever done, the audience really indicates how the show's going to go. You see, what are they into if you have to work a little harder for some audiences? Some audiences are a little quieter, some give it up right away, and it's like a hot, wild show. Also, we have this incredible band who has energy like I've never seen. Gracie Lawrence-

Alison Stewart: She's so funny.

Cecily Strong: -she's like not a human. I don't know how she does it.

Beck Bennett: She said she's never taken singing lessons, which [unintelligible 00:14:23]

Cecily Strong: I'm just like, did I have that kind of energy in my 20s? I don't know. I'm very far from it now. They're incredible, and I'm like, they do 90% of the work to get everybody there. Then we just are lucky enough that we get to show up and then read Simon's very funny words.

Alison Stewart: How did Lawrence get involved, Simon?

Simon Rich: I was a fan of Lawrence, but I'd only met them a couple of times, and Alex suggested that maybe some of their tracks could thematically link to the stories. Boy, was he right, because a lot of people have asked me if they composed these songs specifically for the show, and they didn't. They didn't change a word. I think being New Yorkers themselves, being in this extremely tough, competitive field of professional music making, I think that they were grappling with the same kind of themes that I was in my 20s.

They've written this cluster of songs which are front and center in the show that are about all the themes that the stories are about fear of failure, insecurity, jealousy, bitterness, and just trying to survive in this make it or break it landscape. Also, in addition to performing these songs, they also live-score all the stories and do live sound effects. It's like going to 30 Rock in 1949 and seeing a radio show. You get to see them do the live Foley work and do the horse clops and all the rest. That's a really fun, dynamic part of the show, too.

Alison Stewart: Oh, there's so much fun. We've had them perform live here.

Beck Bennett: Oh, yes.

Alison Stewart: Such a good time. When you're on stage, especially when Jim Gaffigan's on stage, there's a little bit of breaking that goes on.

Cecily Strong: A little bit, sometimes. Don't tell Simon. Simon, that's not true.

Simon Rich: Simon, that's not true.

Simon Rich: Okay, cool.

Alison Stewart: It happens. Do you go with it if you find yourself breaking?

Cecily Strong: Of course. I think part of the fun and part of the show is that you're coming to see a comedian that you like and you want to see them as well. In those moments, it's like you are seeing Cecily laughing at Jim Gaffigan. There's been funny things. In [unintelligible 00:16:42], I won't give too much away, but Jim does play a half-man, half-ape superhero. He's so much physicality in that. That changes every night, and it's always like, "Okay, I'm going to--" I watch as an audience member on stage, like, what is Jim going to do tonight with this?

Alison Stewart: What do you do when you break?

Beck Bennett: What do I do when I break? I guess laugh.

[laughter]

Alison Stewart: Just go for it.

Beck Bennett: I guess I'm laughing when I break. I try to just be comfortable with whatever is happening. Just to go with it and not to be too distracting if I do break.

Alison Stewart: I know you have to go because you have to go to rehearsal, but I did want to ask you about your new podcast.

Beck Bennett: Oh, yes.

Alison Stewart: What's Our Podcast? Brand new. You're in a studio, you're around audio professionals.

Beck Bennett: Yes, it is. Absolutely.

Alison Stewart: Tell us a little bit about it.

Cecily Strong: You said this was your first radio interview.

Beck Bennett: This is my first radio interview, but I do have a podcast. The podcast is different.

Alison Stewart: You understand this room?

Beck Bennett: It's a little bit like this. We don't have the glass wall with the other people in there. It was my first time--

Alison Stewart: You have a two-way mirror, though, right?

Beck Bennett: Yes, of course. The podcast is called What's Our Podcast? It's with me and Kyle Mooney. The idea for the show is that we don't know what our podcast should be about. We have guests come in each week and tell us what they think our podcast should be about, and then we go into another studio next door and try that podcast with them. It's very loose.

Alison Stewart: It's good and funny.

Beck Bennett: Oh, thank you so much. We've had a great time, and we approached the show at the beginning with like, "What are we doing? We don't know how to do this." It was very meta examining all the things as we went. Now we've gotten into a groove, and it's figured itself out, but it still is under that idea of like, we don't know what we're doing. Maybe you could tell us. It just throws a wrench into the interview when we go a different direction, and it's really fun.

Alison Stewart: You are working on something else to do this show. What are you going back to?

Cecily Strong: I'm working on an Amazon show that's in the boys universe, which is very new and fun for me.

Beck Bennett: I love that. Love that universe.

Alison Stewart: That's exciting.

Cecily Strong: That's been a fun thing that I lucked into.

Alison Stewart: Simon, what's next for you?

Simon Rich: It's a lot of screenplays, but they don't let the screenwriters talk about them.

Beck Bennett: Simon, me and Cecily could talk to you about it afterwards.

Simon Rich: Okay, great.

Beck Bennett: I'll reach out right after. Perfect.

Simon Rich: Fantastic. Perfect.

Alison Stewart: We've been talking about All Out: Comedy About Ambition. My guests have been Cecily Strong and Beck Bennett, as well as Simon Rich. Thanks for making the time today.

Cecily Strong: Thank you.

Beck Bennett: Absolutely. Thanks for having us.

Cecily Strong: Thanks for having us.

Alison Stewart: Get to rehearsal.

Simon Rich: Thanks for having us.