In the 45 years of combining observational humor and spontaneity as a stand-up comedian, Paula Poundstone became a master of the stage, while also branching out into numerous other artistic avenues.

Several HBO specials led to a short-lived show of her own, appearances on “The Tonight Show,” joining a reboot of the game show “To Tell The Truth” and becoming a regular panelist on NPR’s “Wait, Wait… Don’t Tell Me,” followed by the prompting of her own podcast, “Nobody Listens To Paula Poundstone,” and even making a voiceover cameos in Pixar’s pair of “Inside Out” movies.

Chicago Concert Reviews received a wonderfully witty call from the multi-faceted entertainer and best-selling author on her way to pouring the City Winery a double cocktail of comedy on New Year’s Eve, which is Tuesday, December 31 to be exact, for an early show at 7:00 p.m., followed by 10:30 p.m. to officially ring in 2025.

Do you have anything special in store for the City Winery on New Year’s Eve?

Paula Poundstone: Do I have anything special in store? No, I really don’t (laughs). That’s a very disappointing response, but my plan is to be funny. If you went to two of my shows in a row, they wouldn’t be the same because I talk to the audience. It’s my favorite part of the show. I do the timeline of, “Where are you from? What do you do for a living?” Little biographies of audience members emerge and I use that to set my sails. I sort of go in the direction that is there before me, so I could say, “Yes, I’m planning something special.” The special part is that people from Chicago, who were there for New Year’s Eve, will be a part of the show.

Are there any prior hilarious or disastrous encounters you’ll never forget?

Poundstone: I don’t remember them very well at all. Okay, there was one time, and this wasn’t really an interacting with the audience thing. It was a show I was at many years ago. I almost never have had someone thrown out or something like that. It’s just not the nature of my audience and it’s certainly not my nature either. Yes, I talk to people, but it’s not like heckling. It’s not combative. But there was a night, and it still wasn’t combative, this particular venue I was at had tables and there was a table right beside the stage. In fact, I think it was in Chicago maybe. There was a couple making out and they were really going to town to the degree that everyone’s eyes started to turn to them, and at one point when they come up for air, I said something to them like, “Geez, it’s kind of funny that you’re here.” The whole crowd was laughing because it was funny, but it was really distracting and so I kinda was like, “Could you maybe [tone it down]?” I’m sure I didn’t say, “Oh security, come get them.” I can’t imagine I would have done that. But I think at one point, maybe one of them got up to use the restroom or something (laughs) and they got thrown out. For the rest of the night, as me and the audience discussed what had happened, we referred to them as “the love criminals” and it was funny.

I’ve been doing this job for 45 years. I’ve really gotten to a place where I don’t have everything itemized in my head anymore. I know I was in Portland [last] Saturday and I talked to a woman who was a veterinarian. I said, “What do you specialize in?” She said, “cats and dogs,” and then something about horses came up. I kept insisting that she was putting saddles on cats, and for the rest of the night [was saying], “you get off those cats” and the audience was totally with me, totally in support of this idea…I finish one and I’m ready for the next one. I have no dust from the old shows still on me when I go to the new one.

What comes to mind when you think of performing around Chicago?

Poundstone: “The Bean.” I like to see “The Bean.” I don’t always go to “The Bean,” but when I do, I’m happy I did. I like to go to the Italian Village where you go up the stairs. That’s a great restaurant. I’ve been there many times. I don’t do a whole lot else when I’m there for “Wait, Wait…Don’t Tell Me!,” which I am every so often. We get told the topic of the bluff story part of that show, of that game where each of us reads a news story and only one of them is true, but we don’t get told what the sort of umbrella topic is for the news story that we write until, like, the day before. So usually I’m still writing on the day of the show, and therefore, I barely leave my hotel room.

What has it been like to be a regular part of that program?

Poundstone: It’s been 23 years! It’s delightful. It’s really, really fun to do. Part of what’s fun about it is, well, A, I usually work alone, so it’s exciting to work with other people. B, I don’t find in all the years I’ve been there [that I’ve had any negative experiences with anyone]. I don’t know how many panelists they have now, 15, 20, so I’m not always with the same people and sometimes it’s newer people. The other night I was on with someone I never met before, very nice, very funny. When somebody throws a joke out, somebody else thinks of something to add on to it. It’s really just fun. I’ve never known anybody to go away and go, “well, that was mine,” you know? It doesn’t feel like there’s a lot of ego involved in who talks when and who says what, which makes it a lot more fun.

You’ve been on a ton of TV programs too. What are some that stand out?

Poundstone: I did a bunch of different things for HBO. I did a talk show for HBO that was very short-lived but fun. We taped four [episodes] and it never made it any further than that. There’s a lot of stories like that with my career, but nonetheless, it was really fun to do. I did an hour special for them a thousand years ago called “Cats, Cops And Stuff” that was awfully fun. In fact, I remember one time back when American Airlines used to have the little television screens that were hanging from the ceiling, or maybe it did have the individual ones in your seat, because they had a little guide to what you could watch. All I know I was walking down the aisle of an American Airlines plane and f*** if people weren’t watching “Cats, Cops And stuff” on their American Airlines televisions, which was flattering of course and I also felt like a geek.

Let’s see, I did a remake of “To Tell The Truth” somewhere in the [early 2000s]. It was great. It was with my regular panelist partner, Meshach Taylor, who was brilliant, and funny and a joy to work with. He and I could just never get over the fact that we were paid money to sit in a chair, and laugh, and play a game, like, “wow, I have like a PhD in that!”

What was it like going on loads of late night shows? You were on “The Tonight Show” a lot and I believe you were first brought on to “Saturday Night Live” by Robin Williams.

Poundstone: That’s right, I was. I just did stand-up there a thousand years ago. This was the Eddie Murphy cast, that’s how long ago it was. I did a bunch of “Tonight Shows.” I did a few with [Johnny] Carson and I did many with Jay Leno. I got to go cover the conventions for Jay when it was [Bill] Clinton and the first George Bush. I did four nights or five nights at the Democratic Convention and the same thing at the Republican Convention. Then I also went to Washington to cover what ended up being Clinton’s inauguration and it was really fun, partly because the only thing I ever rehearsed or even knew prior to just the last minute was where I would be when he came to me.

He would be at his desk and then he would go to me via satellite repeatedly during the show. But I really didn’t know what I was gonna say. I mean I knew I had something short of an idea, which I’ve always referred to as an inkling. I had an inkling before he would come to me, but not much beyond that, which made it really especially exciting and part of that was just logistics. There was no time to figure everything out ahead of time, but I think it’s better that way anyways.

You’ve worked with so many iconic stars. Can you tell us about a few that meant a lot to you?

Poundstone: Well, I was friends with Mary Tyler Moore back when she was alive, cause that’s the best time to do it! She was a great supporter, very kind to me. I met her just doing one of those comedy award shows. Not being a total idiot, when I went to the rehearsal, I brought my baby with me so I could get a picture taken with her. That’s how I got my foot in the door and we became friends over the years.

You know Robin Williams was certainly a great help to me, but I have to say Robin Williams was a great help to most comics. Anybody my age or younger that’s a comic owes a debt of gratitude to Robin Willams because he really, almost single-handedly, re-ignited the audiences’ interest in stand-up comedy. Obviously, stand-up comedy has been around since before we came out of the caves, but you know, interest in that form ebbs and flows as years go by. Robin just brought this whole new way of doing it and a tremendous amount of energy, excitement, and brilliance and people came out. I happened to live in San Francisco for awhile as a young comic and people there came to the comedy clubs. We had a really dynamic, vibrant comedy scene in San Francisco back then. This would be the early ‘80s. People came out thinking he might stop by and the truth is he did stop by. He stopped by all over the country. He could be working a 3,000-seat amphitheater in Cleveland, and at the end of the night, he would stop by Uncle Funny’s Yuck House. There isn’t a comedy club in the country that doesn’t have a picture of Robin Williams on their stage. What happened was, especially in San Francisco, people came out hoping they might see him and they saw the rest of us. They were kind of like, “hey, we like that too.” They didn’t like it frantically the way they liked Robin, but that gave a lot of us a toehold, and you know, just time and place.

How was it transitioning towards podcasting for “Nobody Listens To Paula Poundstone”?

Poundstone: Podcasting has some advantages to stand-up and some disadvantages. You don’t have anybody to tell you, like if I say something on stage and it doesn’t go over, I can either abandon it or retool it for the next time. I might realize, “oh, you know what? I didn’t say it the way I should say it. I should say it a different way cause I still think it’s a funny idea. I just didn’t put it out there right.” With podcasting, I get no feedback, but here’s what’s great about that.

For example, on our podcast, I occasionally do characters. I would never have the courage to do that in front of an audience, never. I tried once a thousand years ago and I chickened out. I still have a little layer of flop sweat on me from the time I tried in the ‘80s (laughs) to do a character on stage, but because I get no audience feedback [when I’m recording], I can just tell myself that I think it’s great (laughs). [After it airs], now we get Facebook, Patreon and email [messages]. There are wide ways of people corresponding with me and a lot of my “Nobody Listens To Paula Poundstone” fans come to my shows and then they’ll say to me or they’re write to me, “Oh, I really love Mrs. Culpepper. Oh, I wish there was more of Mike ‘Boom Boom’ Bonafit,” and then my god, there’s no stopping me after that. Once I hear a little bit of encouragement, I’m off and running. It’s fun to do stuff that I wouldn’t do in stand-up, stuff that breaths a little bit for one thing. We have the goofiest elements on the podcast and part of the reason I do it that way is because I know it’s goofy. We had an episode one time where I interviewed a mime and had him teach me some mime. It is an audio medium and I’m aware of that!

We have a book club. Occasionally, someone will tell me they read the book. In fact, in Portland the other night, somebody came up to me with a copy of the book that we’re now reading in our book club, asked me to sign and I signed it as if I had written the book. When are you gonna do that? Just silly ideas that wouldn’t have life in any other format. That part has been fun.

I don’t listen to mine, but as a podcast listener myself, I’m well aware that there’s this sort of funny relationship, because for me, I listen on my [phone] and I carry it around in my pocket. When I’m listening to stuff, I walk the dog with it. I clean the house with it. I sift the litter box with it. I fall asleep to podcasts a lot of times, and then I back up when I wake up again and hear the part I missed. There is sort of an intimate friendship with the podcasts that you like. We were just talking in a production meeting the other day and one of our producers was pointing out that, technically, in terms of our contract with the network that we’re with, we don’t have to do a show every week. We could take a break over the holidays and not do a show, and I’m just like “nah,” because the people listen, especially over the holidays. Somebody who feels really attached to the podcast will feel lonely if we don’t do one. Sometimes we do it ahead of time, but I make sure there’s a fresh program on every week.

What has voicing Forgetter Paula in Pixar’s “Inside Out” series added to to the equation?

Poundstone: You would think a little more of that would rub off on me, wouldn’t you? It’s a very small role. We were promoting a job that I’m doing in Glendale, California coming up in February. I was reading copy for a radio station that’s helping promote [the show] and we needed to cut something for time. They had me saying something about ‘Inside Out’ and even my manager said, “Don’t say the ‘Inside Out’ thing.” She goes, “It’s such a small part. And I was like, “Okay, look a**hole, yes it’s a small part (laughs), but it’s in a Pixar movie! The truth is I can’t say that it’s done anything at all for my career, but for me as a human being, it was a dream come true.

I mean I would love to have a bigger part. I keep writing to [director] Pete Docter, who made the first one, asking him if there could be a sequel where Riley gets amnesia. Maybe she hits her head or something because that would include the Forgetters a lot more, and me and Bobby Moynihan, we’d be the stars! You know what, Pixar movies are such a cut above to begin with. For two of my children, a “Toy Story” movie was the first thing they ever saw in a theater. I feel like they’ve grown up with Andy, the kid who owns the toys, and the stuff they’ve done is just f***ing amazing. I don’t know where they’re gonna find one more set of things that talk (laughs). So to have been even the teeniest, tiniest part of a Pixar film just makes me really, really happy.

Those “Inside Out” movies are really timely, especially this most recent one, because it’s funny that it introduces the character of Anxiety and the whole nation is, well, maybe not the whole nation [is feeling that emotion right now]. I think there’s some people who should have anxiety and don’t, and that’s probably why they vote the way they do, but a popular majority of the nation is struggling with anxiety right now, so to be able to sort of like, really in a relatively scientific way, identify what that is, and why it’s there, and to be able to laugh at it, I think is enormously helpful. In the first place to young people, but just like “Sesame Street” had that same sort of model, which was programming for kids, but it was really entertaining to the adults that watched it as well. There was a couple of layers always in the material and this is just so brilliantly done. Understanding our anxiety is gonna be a part of what gets us through the mess we’re in, if we in fact get through the mess we’re in.

Is there anything else you’d like to add about ringing in 2025 with the City Winery?

Poundstone: I’m really looking forward to it…These are stressful times. These are really challenging times. Maybe people don’t think about it as much as me. I don’t think so though. I think a lot of us are in this same boat. For me, I go on and it’s two hours of either just forgetting about some stuff, or when I make jokes that are current events-based, laughing at it. It’s been a helpful elixir for me to get through all this and I think it provides the same service to the audience. I sure hope it does. It’s reciprocal. It’s a good thing for the brain, serotonin I think. Get a little happy brain chemical there. I don’t know how long it lasts, but I’m doing two shows that night, so I’m going to have an extra serving!

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Paula Poundstone performs at the City Winery at 7:00 p.m. and 10:30 p.m. on Tuesday, December 31. For additional details, visit PaulaPoundstone.com and CityWinery.com/Chicago.