Alison Stewart: This is All Of It on WNYC. I'm Alison Stewart. Just a reminder, WNYC is teaming up with the New York Blood Center for a one-day blood drive. It's taking place this coming Tuesday, December 9th, from 9:30 AM to 2:00 PM, right here in the WNYC Greene Space at the corner of Varick and Charlton Streets. You can do something good for your fellow New Yorker, and you can do it from our performance space in Lower Manhattan. To sign up, head to nybc.org/wnyc. That's NYBC, stands for New York Blood Center, dot org/wnyc. That's in the future. Now we have an hour of concert previews for you. Let's start with Ana Gasteyer.

[music]

Alison Stewart: Sugar and Booze is the name of Ana Gasteyer's holiday spectacular happening on December 15th at the Town Hall. Take a listen.

[MUSIC - Ana Gasteyer: Sugar and Booze]

Bells are ringin' and a jinglin'

Folks are mixin' and a minglin'

Twinklin' lights and tinsel on the tree

How I love to keep the yuletide gay

Call me corny or cliché

But there's a reason that the season brings so much joy to me

I love snowmen and turtle doves in twos

Holly, ivy, mistletoe, can take away my blues

Chris Kringle and his reindeer friends, they endlessly amuse

But the best part of the holidays is sugar and booze

I love mittens and skating on the ice

But I glide right through December, mixing naughty with that nice

So pour a nip into that nog and let it light your fuse

Because the best part of the holidays is sugar and booze

Alison Stewart: Ana is a wonderful singer. She trained at Northwestern before this thing they referred to as comedy came calling. Whether it be on Saturday Night Live playing Martha Stewart or lampooning public radio or on its lute as an uber wealthy divorcee, or on Broadway and Wicked, or in Once upon a Mattress, Ana is a delight. She joins us to give us a preview of her concert. Welcome back.

Ana Gasteyer: Yay. Thank you so much for having me.

Alison Stewart: I told you I'm going to your show. I bought tickets. I invited friends to come to your show. What do we need to know? Do we dress up?

Ana Gasteyer: Yes.

Alison Stewart: Is there audience participation?

Ana Gasteyer: Yes.

Alison Stewart: What do I need to know?

Ana Gasteyer: All of the above. Obviously, it's me. It's a little comedy, it's a lot of joy, and it's a collection of seasonal secular favorites, as I like to say. We're going to celebrate the holiday. We're going to let it rip. Town Hall's been coming up with some cool custom drink ideas and specialty beverages. I like a Christmas sweater. I'd like a white elephant re-gift. If you've got a dud hanging around in the closet and you want to get rid of it, we've got some games; we're going to play with it on stage. Basically, yes, we're just going to laugh a lot and sing a lot. We've got a full horn section here in New York, which is always my favorite because I have a big, loud, horny voice, if you will.

Alison Stewart: [laughs]

Ana Gasteyer: Yes, we're going to let it rip. My bandleader, Julian Fleisher, is going to be with us, and I'm really excited. This is my favorite band. We've worked together a long time, and the opportunity to do it in a big, storied venue like Town Hall is so exciting.

Alison Stewart: I was going to ask about Julian Fleisher. What do you like working about with him?

Ana Gasteyer: Julian and I have been working together for like 20 years. He produced my first album, I'm Hip, and he produced my second album. He's like a savant. He's a really talented music producer. He hears comedy really well inside of music, which is not the most-- It can be an overly earnest skewing group. It can also be a ridiculous skewing group. I live squarely in the middle of these two personas that I have, my comedian persona and my musical Persona, which you encapsulated beautifully in the introduction.

It took me a long time to fuse them because I really went from funny SNL wig lady to-- I started as a music major as you described, and then I fell down the comedy rabbit hole at Northwestern, and then went out to LA and did The Groundlings and sketch. Music was just something in my toolkit. Then, when I left SNL, I dug deeper, did a bunch of Broadway shows, started studying again, and when I started putting my own act together, kind of found this really fun marriage between-- It's very throwbacky, it's very nostalgic, sort of Rosemary Clooney, maybe my Idol, like late entertainers, late '50s, early '60s entertainer era of broads who could stand in front of a band.

Alison Stewart: Broads.

Ana Gasteyer: Yes, broads who could stand in front of a band and deliver a joke. I feel like I do both well. Julian helped me tap into that part of myself. I love arranging with him, I love writing with him. There's just always a sense of joy. It always leads with joy, which is why the holiday album, I think, has persisted. It's a five-year-old album, but as we've continued to tour, we pick up loyal traditionalists every year. The holidays do that. They have this throwback sense of tradition that people want to come together and celebrate. That's what the show aims to do.

Alison Stewart: I think people need joy in their lives right now.

Ana Gasteyer: [chuckles] Yes.

Alison Stewart: They really do.

Ana Gasteyer: They do. That's why we give away prizes. I collect things throughout the year. I keep all of my husband's Delta first-class amenities kits. I think it's important for people to feel like they can fly first class, even if they're sitting in first ass, as we like to say. I go around my house and meet both of my needs. I purge things I no longer want, and I give gifts to others. [laughs]

Alison Stewart: Sounds perfect. It sounds perfect.

Ana Gasteyer: Come on down to Town Hall for some of Ana Gasteyer's crap.

[laughter]

Alison Stewart: Oh, that's so funny.

Ana Gasteyer: We have a few new songs, too. I'm going to bust out the fiddle for the first time in a long time publicly.

Alison Stewart: Oh, my gosh. I knew you played fiddle.

Ana Gasteyer: Many people don't, and they're shocked to learn that I do. I'm still shocked. I did go to fiddle camp for my 50th birthday, and so I felt that I had to add that-- I mean, nothing says the holidays like fiddle.

Alison Stewart: Not violin, though.

Ana Gasteyer: No, not violin. It's all in the attitude.

Alison Stewart: I was about to say.

Ana Gasteyer: Sad violin. If you want a wistful, sad holiday song, maybe I'll write that just in time.

Alison Stewart: Now you have shows planned for across the country.

Ana Gasteyer: Yes, we're running across the Midwest next week.

Alison Stewart: Hopefully, you already played in Philadelphia, yes?

Ana Gasteyer: We did, yes.

Alison Stewart: What did you learn from that show that's like, "Yay, we're going to do that again," and other times like, "No, we're going to pass on that"?

Ana Gasteyer: We never pass on anything because there's nothing but a good discovery. I would say I talk a lot. I'm a talker, and I have a long set list, so I always have to be very mindful of what pearls are worth sharing and which are best kept. We forgot to bring the prize box on stage, so we did have to do some vamping.

Alison Stewart: Okay. Remember, prize box?

Ana Gasteyer: Yes, we have to bring the prize because everybody wants prizes.

Alison Stewart: Everybody likes prizes.

Ana Gasteyer: That's the whole point. Everybody likes a prize, a holiday prize.

Alison Stewart: Your next show, I think, is in Minneapolis.

Ana Gasteyer: Yes.

Alison Stewart: How are audiences different from region to region?

Ana Gasteyer: That's such a great question. The Midwestern crowd really leans in heavy on the Hallmark side of things. They really go for the costume, which I really enjoy. There's a lot of tartan, there are a lot of bows. People deck it out, and they get their hair done, which I enjoy. There's some hot rollers in the house. This will be my first year in Minneapolis. I'm really looking forward to it. We've never played there, but we always play Chicago, and I originated Elphaba there, so I have a very loyal and lovely fan base.

First of all, my favorite vintage shop is there, so I always try to get it on the-- so I can stop by Secret Treasures in Evanston. We do actually add my merch this year. I have a bunch of vintage curated.

Alison Stewart: You are wearing--

Ana Gasteyer: I'm rocking the merch.

Alison Stewart: Very cute merch.

Ana Gasteyer: I love my merch. I like my holiday stuff. I like the holidays. We did a curated vintage collection this year, too, which was really fun. Secret Treasures is always a stop along the way. Anyway, it's not really answering your questions. There's just a joyous sense of tradition in the Midwest, I would say. That said, I've played New York now several years, and it's always wonderful because we land here. It's this kind of savvy homecoming. It's Smartypants in the audiences in New York. I always feel like I can tell the truth 100%, because I'm a New Yorker, and it is always very close to the holidays.

I don't know, the fact that I like to think of my show as a holiday party, and I feel like people treat it that way. At least historically, one of the highest compliments is that I feel like people show up in the way that you would to a holiday party, that they dress up, they come out, they have their cocktails, they come together, whatever, their crew, their family, their mom group, whatever it is. People tend to festoon themselves. I applaud that because it--

Alison Stewart: I'm planning an outfit in my head just as we're talking.

Ana Gasteyer: I bet you are, because you've always got the looks.

Alison Stewart: It's got fur a little bit on the arms, a little bit of fur around the edge.

Ana Gasteyer: Exactly. Everyone has more plaid and holiday sweater in their collection. I have four pairs of tartan shoes at this point, and I don't have anywhere to wear them because I'm always performing it on the road.

Alison Stewart: Tartan shoes. I can picture it. Ana Gasteyer is my guest. Her holiday spectacular, Sugar and Booze, is happening at the Town Hall on December 15th. You said you're going to Evanston?

Ana Gasteyer: Yes.

Alison Stewart: It was 15 degrees in Evanston yesterday?

Ana Gasteyer: Yes.

Alison Stewart: How do you take care of your voice on the road?

Ana Gasteyer: It's such a thing. I have to travel with a humidifier like a nerd. I have glycerin spray, Entertainer's Secret. I have all of these on a TikTok that went weirdly viral last year. I use these cough drops, Grether's, which all the Broadway people use, but I also use-- what are they called? Something Brothers. Pine Brothers. It's super OG. It's like they've been in a vault from the '50s, but sometimes you find them in like Rexalls, like old-timey drugstores, like call your neighborhood druggist.

They're called Pine Brothers cough drops. They're just glycerin. Most of it is just humidity and water, water, water, water, water. You can't really booze it until after you're done, which kind of sucks because the show's called Sugar and Booze. I'll entitle myself to a delicious cordial when I'm done.

Alison Stewart: What did you learn at Northwestern-

Ana Gasteyer: Nothing.

Alison Stewart: -about your voice?

[laughter]

Alison Stewart: I learned how to make fart sounds under my armpits, which you still use this day.

Ana Gasteyer: I trained in high school, and I trained at Northwestern. I definitely know how to breathe. I learned diaphragmatic don't-giggle breath. I think that's always been there. Like all of that fake legit stuff I do as Bobbi Mohan-Culp, my character, the middle school music teachers I did with Will Ferrell.

Alison Stewart: Oh, we're getting to her.

Ana Gasteyer: That's all in there. I learned, obviously, the most about my voice from eight a week. You just learned that from Wicked, from Threepenny Opera, from Passion. I had this great sequence because I did Elphaba in Chicago. Then I came here, and I did Threepenny Opera on Broadway. Then I did Elphaba on Broadway. Then I did Passion, Stephen Sondheim's show, again in Chicago. I went basically from screaming belt lady to legit to screaming belt lady to legit, which, muscularly, was just a happy accident for my voice because all of that Elphaba screaming is not good for you day after day after day after day. You have to live like a nun, but the legit is just better supported, period.

It just lives in a different, less dangerous place in your voice, for the music nerds out there, or voice nerds. Sleep is the number one antidote to everything, period, the end. From Northwestern, I learned how to breathe. From Broadway, I learned placement and safety. Last year, I did Mattress. Working with my own band and working with American songbook standards and jazz and lyrically-driven music and comedy, frankly, for Bobbi and Marty and all the characters that I've played, because there are notes that I can sing in character that I often don't believe I can sing.

Alison Stewart: Oh, really?

Ana Gasteyer: If you just put the music in front of me, I'll be like, "Oh, I can't hit that." Then, musical directors I've worked with are like, "I have heard you do that as a character." I've learned from being on my own with a band and really leaning less about how other people think it's supposed to sound and more into just whatever's fun, that there's more flexibility in my voice than I ever would believe.

I think if you're a rule follower, the voice lesson part of it and the Broadway part can be pretty uptight because you're living inside somebody's instructive manual and you're trying to deliver something that you feel they want to hear, as opposed to the freedom of working with my own band and making my own music. When I started writing songs was when I really started-- I've always written comedy songs, but when I wrote songs for Sugar and Booze for the album, I just started making choices that I didn't feel judged around because it was my own judgment. Does that make sense?

Alison Stewart: It does. As you said, you're really big into the holidays.

Ana Gasteyer: Yes.

Alison Stewart: New York magazine asked you for your gift-giving strategy.

Ana Gasteyer: Yes. One of the highlights of my life. [laughs]

Alison Stewart: My friend was like, "You're going to interview Ana Gasteyer. Ask her about these things." They wanted to know all about the things that you suggested.

Ana Gasteyer: Okay.

Alison Stewart: You got a Whirley-Pop. You said it was your favorite thing that you have ever gotten.

Ana Gasteyer: I have a gift guide on my website, anagasteyer.com, where you can also get your tickets to Town Hall. Yes, I have a gift guide this year because I really do-- I'm a Taurus. I do take gift-giving very seriously. Like I've had the dream that people have, where they have to finish their math exam in high school, about not having the right presence for people. I'd rather not give a present at all than give a crappy, stupid, just buy something to have it.

I really like giving gifts that are practical, that fix someone's life, that make their life better, either in an aesthetic way, because it's a pretty elevated version of something, or because it's a little bit nicer than they might swing for themselves, the thing that they're like, "That would be he nicer--" If there's pragmatism at the heart of it, I also love that. Like, if you can get Dr. Teal's foot magnesium spray, there's this hot-to-trot magnesium spray for people's feet to help them sleep right now, that's like $70 a bottle. You can get Dr. Teal for $5, and it's the same ingredients. I'm all about that, or the Trader Joe's Retinol. Go for it.

[laughter]

Ana Gasteyer: The Whirley-Pop is this ridiculous-- This friend of mine at Saturday Night, a writer, gave it to us one year. She was just giving out holiday gifts because she had the holiday spirit. It's this old-fashioned popcorn maker. It's stovetop, and it makes the most incredible popcorn. We've probably given that gift 20 times since I got it. It's just a great gift. I love a good salad bowl. Go to my gift guide. Seriously, I really-

Alison Stewart: It's really good.

Ana Gasteyer: -put some time in it. Not just the one on The Strategist, but the one on anagasteyer.com because I really am proud of the-- I don't know, it's ridiculous that I spend time on this. I like giving something that makes someone's life better. Like a super fancy umbrella that they would never buy for themselves.

Alison Stewart: You're pro gift card, though.

Ana Gasteyer: I am pro gift card, which people find scandalous, but I would rather someone use the thing and make their life better than re-gift it at my show.

Alison Stewart: [laughs]

Ana Gasteyer: Especially for you, a teenager too. I actually think gift cards are great for teenagers because they don't really want to be cornered or labeled. Also, if you know they're going to use it-- I mean, my son will probably go to use a-- I've given him Cane's chicken. I've given him Chipotle cards. They make a very handy all-purpose. Also, people who give you-- I don't know, anytime you're having a bad day, I feel like a gift card is just like an extra bonus.

Alison Stewart: Oh, free money.

Ana Gasteyer: Free money. Right.

Alison Stewart: Free money.

Ana Gasteyer: Like, you're on jury duty, you've got the blues, but oh, my God, you can get yourself a Starbucks.

Alison Stewart: [laughs]

Ana Gasteyer: You know what I mean? Or it's raining. I like rain things. That's why I like a nice umbrella. I like cute wellies because if it's raining and you're sad, then you're like, "Oh, I get to use my fun umbrella, though." [laughs]

Alison Stewart: You said, though, in the article that the worst gift you ever got happened when you were seven years old, and they were tights, were the same vintage. Tights were bad when we were little girls.

Ana Gasteyer: First of all, they float. All of them float. It was like crotch float.

Alison Stewart: Exactly, right?

Ana Gasteyer: You could sort of waddle around.

Alison Stewart: She's the same age. You all wore tights.

Ana Gasteyer: They were around your knees.

Alison Stewart: Yes.

Ana Gasteyer: They were around your knees, just kind of bunchy and prohibitive, itchy, just generally unpleasant. Somebody gave me, I remember, and it was like back in the day-- Children don't have to do this anymore because they live a privileged life, but we used to have to gather and then open everything in front of everyone. Do you remember that?

Alison Stewart: Oh, yes.

Ana Gasteyer: Then you would have to look excited about the tights because you couldn't hurt anyone's feelings. I think I burst into tears and was separated in that particular incident, which is why I remember it. It was a pair of navy tights.

Alison Stewart: That's sad.

Ana Gasteyer: Isn't that sad?

Alison Stewart: That is sad.

Ana Gasteyer: That is not a Barbie. [laughs]

Alison Stewart: Let's talk about something more fun. My guest has been Ana Gasteyer, by the way. Her holiday spectacular, Sugar and Booze, is happening in the Town Hall on December 15th. Come to the show. I'm coming to the show. It's going to be really, really fun. 2025, it was a big year for SNL, the 50th anniversary show.

Ana Gasteyer: Yes.

Alison Stewart: When you look back on your period in that period of your life, what is something that you just won't forget?

Ana Gasteyer: Saturday Night Live times?

Alison Stewart: Yes.

Ana Gasteyer: Saturday Night Live. Why did I say it that way? It's like a voiceover reading.

Alison Stewart: Saturday Night Live?

Ana Gasteyer: Saturday Night Live. I don't remember much because I literally didn't sleep and was just adrenal. I can't believe that I was dropped into this life between The Groundlings and SNL. Groundlings also turned 50 this year, as did the improv show I was a part of at Northwestern. Something was in the water in 1975. My favorite memory, universally vibe-wise, about SNL was we would write all night Tuesday. For the most part, that was like all things creative. About 11 hours of dread and 1 of ecstatic joy. We're just avoiding, avoiding, avoiding, avoiding. Then you get the thing done, and then it's like your favorite thing you've ever done.

Every now and again, you would write something that you were so excited to bring to the table later on that day, to the read-through table. That pure, just psychotic mirth after like an hour and a half of sleep, heading uptown to the read-through table, knowing that something delightful was about to happen that you were going to bring to the table. That was the greatest feeling in the world. I loved the rewrite table. Writers hate the rewrite table. They all find it absolutely miserable. I could never get over the fact that I'd written something, and then I got to have this team of whatever, 20 experts sit and punch up my sketch. I mean, that's like the greatest privilege in the world.

When Rachel Dratch and I wrote-- we wrote this holiday, another Christmas thing. We wrote a Hallmark holiday parody. It's called a Clüsterfünke Christmas. You can watch it on Paramount. Plus, when we wrote that, we had like a little punch-up room. That was one of my favorite parts of that experience. We had six of our favorite comedy writers just spend a day, again, punching it up and finding better jokes. There's just nothing better than a hive mind of comedic people in one room.

Alison Stewart: At the 50th anniversary, you performed as the Culps.

Ana Gasteyer: Yes. [laughs]

Alison Stewart: Wikipedia describes them as, "Marty and Bobbi were an awkward, unstylish married couple who served as music teachers at Altadena Middle School. In the sketches, they would perform prim, conservative medleys of modern pop, R&B, or rap songs at various school functions, much to the embarrassment of their unseen son, who attended the school."

Ana Gasteyer: "Unseen son." That's funny. That's the Wikipedia part.

Alison Stewart: Yes.

Ana Gasteyer: I was waiting for the Wikipedia shoe to fall. I don't know who they're talking about.

Alison Stewart: Okay.

Ana Gasteyer: Anyone in the audience was bummed. I mean, the premise was always that it was a real bummer that you got Bobbi and Marty at your prom or whatever.

Alison Stewart: You decided to perform, as part of your contribution to the 50th anniversary, a little snippet of Kendrick Lamar.

Ana Gasteyer: Yes.

Alison Stewart: What was difficult about performing Kendrick Lamar?

Ana Gasteyer: Everything. The rhythm is insanely hard. Those medleys are always the last thought, and you don't know that you're going to get the rights until the 11th hour to even do the song. Yes, just finding the rhythm and finding the bit which worked. Also, frankly, that song had eclipsed all possible numbers of whatever revolutions in the world. We actually went back and forth about whether or not we even wanted to do that Kendrick song because we were like-- I think it was just after the Grammys and it had been everywhere, but the universe allowed us to do it and liked it.

Alison Stewart: Because we are a news organization, we're going to play a little bit of it.

Ana Gasteyer: How exciting.

[MUSIC - Will Ferrell and Ana Gasteyer: Not Like Us]

Ana Gasteyer: [laughs]

Alison Stewart: So funny.

Ana Gasteyer: Somebody in one of the early comments, because it went totally viral, obviously, and it was so fun to read the comments, somebody wrote, "Throottoottoot," throottoottoot, which really made me laugh.

Alison Stewart: [laughs]

Ana Gasteyer: It was so fun. It was one of the most fun things I think I've ever gotten to do.

Alison Stewart: Something else that is really fun is, someone should go on your Instagram page, because at the Thanksgiving Day parade, you were watching Ragtime.

Ana Gasteyer: I know.

Alison Stewart: You can see you in the back. You're verklempt.

Ana Gasteyer: I got verklempt.

Alison Stewart: They're performing, and you were at the back like, "Oh, my--"

Ana Gasteyer: The embarrassing Broadway mom.

Alison Stewart: What were you thinking when you heard the performance?

Ana Gasteyer: Joshua Henry's voice is just-- I don't even know how a person can sing that well. I know A lot of unbelievable singers, but that music's so beautiful. I just bought my tickets. My parents are much older, and they're coming for Christmas. I just bought my holiday tickets to go see Ragtime. Lear DeBessonet directed Mattress. I've been so, so excited. We were invited, maybe 10 years ago, to sit in the front row at Macy's. I didn't know that it was like a special, special thing, those particular seats.

I didn't know they were in the front row, but they were like the 34th Street. I sent my dad and the kids while I cooked. Then we were punished and banished to 72nd Street for the next 10 years. I've done a million interviews with Macy's. I love the parade, so we go every year. When they invited us this year, I was like, "We're not blowing this. We're going to sit in the front row. We're going to look--" I was so excited because the Broadway shows are right there. You get to see everybody warm up. You get to watch every Broadway show. It was really exciting. I got extra excited because it was my personal dresser, Courtney Alfrey, who was there with Josh, so I was really excited.

Alison Stewart: You can see Ana Gasteyer on Monday, December 15th, at the Town Hall for her spectacular Sugar and Booze. We are really excited to see you come back to New York. Have a great time out on the road.

Ana Gasteyer: Thank you so much.

Alison Stewart: Make a U-turn, come on back to 43rd Street. Should we go out on a song with Maya Rudolph, Secret Santa?

Ana Gasteyer: Yes, Secret Santa. One of my faves.

Alison Stewart: Thanks for coming in.

Ana Gasteyer: Thank you.

[MUSIC - Ana Gasteyer and Maya Rudolph: Secret Santa]

Maya Rudolph: Hey, Ana. Where've you been, girl? I didn't see you at the holiday office party.

Ana Gasteyer: Oh, Maya, I'm so glad you called. I need a friend to lean on. I think I got woke this weekend.

Maya Rudolph: Spill the beans.

Call me a banana, but I went down to Havana

To buy my Secret Santa a present today

But I slipped on a banana, woke up in a cabana

Sippin' rum and orange Fanta, so I think that I'll stay

My Secret Santa's rich and handsome

He drives a fancy car

I knew just--