Father’s Day Weekend with “World’s Greatest Dad(?)” A Q&A with Jimmy Carrane

Don’t be the world’s latest dad! Get tickets to Jimmy Carrane’s World’s Greatest Dad(?) before they sell out completely. Jimmy is reprising his critically acclaimed show this weekend in honor of Father’s Day. Two of the three shows are already sold out. Tickets are still available for Saturday night’s performance at 9:00 p.m. at Glenview’s Laughing Academy. World’s Greatest Dad(?) is an inside look at a pivotal time in Jimmy’s life. At age fifty-two, he became a father for the first time within months of his own father’s death. The fusion of these two earth-shaking events led to some nuclear emotional reactions, both comic and profoundly moving.   

Jimmy Carrane is one of the most influential and sought after figures in American improv. He has interviewed Jeff Garlin, Jordan Peele, Keegan-Michael Key, Susan Messing, Tim Meadows, Cecily Strong, Ike Barinholtz, Cindy Crawford and many more as a WBEZ journalist and as host of his hit podcast Improv Nerd.  Students nationwide come to him for improv instruction. His many one-man shows enjoy popular runs at Second City, Chicago’s Solo Sunday and comedy festivals.

It is always fascinating to get an inside look at a public figure’s life and Jimmy’s is intriguing and layered. You might imagine that Jimmy, a North Shore native, revels in his accomplishments. In reality, it’s a struggle. At Second City in the 1990’s, Jimmy worked with Chris Farley, Stephen Colbert, Mike Myers and Amy Poehler, to name a few. As the years went on, echoes of his childhood  –  where dysfunction often outweighed love – haunted him as he watched his colleagues rocket to fame.

Ultimately, he met Lauren, the love of his life, and they were blessed with their daughter Betsy. But childhood has its tentacles and it took a lot of years and reflection for Jimmy to appreciate the unique and ultimately beautiful space that he’s created in this world. In all honesty, he says, he’s still a work in progress.

In World’s Greatest Dad(?), Jimmy is completely transparent, unflinchingly honest and hilarious. He describes the impact of being “a fat kid at 300 pounds at New Trier High School who didn’t fit in” and his relationship with his complicated dad, a prominent lawyer who went to jail for embezzlement, but also encouraged his son’s love for comedy. There’s an unforgettable scene at the funeral where Jimmy’s eulogy triggers a call to the Winnetka police. When Jimmy and Lauren follow their therapist’s advice and have their daughter, fatherhood turns out to be an epiphany. You will not hear a story like this anywhere else, yet Jimmy’s experiences and insights are universally relatable, therapeutic, and uplifting. I was fortunate to see the show last summer at the Elgin Fringe Festival and I absolutely left the show mentally healthier than when I went in. Jimmy has added new stories since then, so I am hoping to get my hands on one of Saturday night’s remaining tickets.

Jimmy kindly spoke with me by phone about life as a comedian, father and son.



Teme: How did you decide to call the show “World’s Greatest Dad(?)” Did you consider any other titles?

Jimmy: I didn’t. It was always “World’s Greatest Dad.” My friend Gary Rudoren who directed me in [my first one-man show] I’m 27, I Still Live at Home and Sell Office Supplies, suggested I put a question mark at the end of it. I liked the question mark because the show is about “am I really a good dad?” Was my dad a good dad? Who’s the world’s greatest dad? There’s good stuff that my dad gave me and there’s bad stuff. I’m sure with my daughter there’s going to be some good stuff and there’s going to be some bad stuff.  You don’t have to be perfect to be a good dad. There is no world’s greatest dad.

Teme: Why is Father’s Day weekend an especially good time to see this show?

Jimmy: Well, a lot of people have complicated relationships with their dad. And this show is funny. Laughter brings people together.

Teme: What do you most want people to know about the show?

Jimmy: There are a lot of themes. At age fifty-two, I became a dad and lost my dad the same year. Somebody said after their dad died, they felt closer to their father. That’s what I feel like as I do this show. It’s a very, very funny show. It’s a poignant show at times and for me, it can be a very emotional show.

I talk about my dad going to prison for a white collar crime. We lived in the suburbs. Back then, you didn’t know anybody that went to prison from the suburbs. Thank God, that’s changed —  that was a joke from the show. I’ve had people come up to me afterwards and say, “My dad did something like that.” There’s so much shame that I carry for my dad and my family for what he did.

Jimmy Carrane/Photo by Jerry Shulman

Teme: Has the show changed from its inception until now?

Jimmy: Yes. You saw the show last year at Elgin Fringe Festival. There were parts of that show that I thought could be funnier, but I just couldn’t get there. Perhaps I was too close to it.  I needed some objectivity and a new approach, so I started to perform some of that material as standup. I didn’t know how it would go because I’m an improviser and a storyteller. Ken Sevara, who is a great comedian, asked me to do a show in Lockport. I was nervous, like, “Oh, this isn’t my crowd,” but it did really, really well.

Since then, I’ve made the material more comedic. I’ve added some pieces, like where Lauren and I take a Lamaze class and I can’t concentrate because a couple brought a cooler. I’m a food addict and was obsessed with what they were taking out of the cooler, so I didn’t learn anything in that class. I’m probably going to add a story about when I was a struggling actor living in a dumpy apartment and I got bit by a mouse. I made the fertility stuff funnier. In a lot of ways, it’s a better show.

Teme: How has the show impacted you?

Jimmy: My big goal is, can I admit stuff that’s hard to admit and laugh at myself? To me, that’s where comedy becomes healing. That’s the holy grail. I don’t always achieve it. Sometimes I’ll admit something and realize, oh, that wasn’t funny-I just creeped everybody out.


Teme: What are you thinking or doing right before you go on stage?

Jimmy: Well, I’m usually terrified. This time I think I’m going to be super terrified. It’s in the suburbs and a lot of people that I know who haven’t seen me perform are coming. Taking in that love and support is terrifying. I want to impress them. It takes me a couple minutes to settle down once I’m on stage.  That’s why the first four or five minutes, I’m talking faster than I usually do.  Maybe I’ll say a little prayer before I go on. Also, before I go on, I think of my dad because it’s really a show about him. I think he would’ve really liked this show. He was by far one of the most supportive people of my comedy. He paid for my comedy classes when I started out. He always asked, “What are you working on?” He instilled “Follow your dreams.” I followed my dream of comedy because of him.

My dad, I think, wanted to be a writer. He was a big reader and he taught me the importance of reading and writing. He sought in me something he couldn’t do, which was express himself. So I think he would be really proud of the show, even though I certainly get some good jokes off at his expense.

Teme: Do your siblings acknowledge your success?

Jimmy: Well, they haven’t come to the show and I really don’t expect them to.

Teme: Do they appreciate all you’ve accomplished for Chicago comedy and improv?

Jimmy: I think they do. It’s me who has a hard time appreciating what I’ve done. I struggle. I’m getting better at this, but I constantly compare myself to other people, and that’s another theme of the show. All these people I started out with in the ‘90s got famous while I’m teaching improv in Chicago, trying to get an Illinois State lottery commercial while they’re on Saturday Night Live. I’ve gotten better at that, but when you start comparing yourself to other people, you always lose.

Teme: You are famous. When I took your improv class on Zoom, people were there from all over the country seeking you out. But I did actually want to ask your advice about conquering the comparing and despairing because I suffer from that too, and it can be really bad. How does one ever overcome?

Jimmy: This week, actually, I had it after a couple shows and it was really bad. It’s shame. It’s homegrown shame. The one thing that I do is get on the phone and start talking about it and admitting it and telling my friends. Then the same thing happens that just happened when you said, “Well, I struggle with it too.” I find out someone else struggles with it and maybe they have some advice how they get through it. When I don’t feel alone with it, it dissipates. I don’t think it ever goes away. I think the old me is always there. But it’s better now that I have tools to deal with it. I have language to speak it, name it, claim it and let it go. That’s what I try to do.

Teme: That’s great advice. I definitely find that it ebbs and flows.

Jimmy: It gets easier, but it’s like jealousy. I’ve been jealous. It took me years to admit. Once I could admit that I was jealous of whoever it was who started out in Chicago … and it was everybody … Once I could admit that, my jealousy left. Does it come up? Yes, it still comes up, but I got to tell you something. I used to get jealous and I couldn’t do anything for weeks. It took me over. Now sometimes it’s just a couple hours, sometimes it’s a half a day, maybe a day, but at least I can keep moving forward.

The other thing that helped me with jealousy, and I feel kind of embarrassed to admit this, but was when I realized that the people who were doing better, or at least what felt like “doing better” – they were on TV and in films or whatever – could help me if I just ask them. “Hey, would you be on my podcast?” or I could call them for advice. When I realized that those people actually could help me, that’s when it also got better.


Teme: What makes laughter so healing?

Jimmy: In the show I talk about how I wanted to be famous. Growing up, my parents didn’t give me much attention. They gave me plenty of food, but they didn’t give me much love, so laughter was a sign of love. Also, laughter is a way of not taking myself too seriously and that helps me feel lighter as a person.  Another thing, too, is that when we laugh together in a group, we’re all one. That experience is very fun and powerful.

Teme: That’s a form of joy that seems specific to comedy. 

Jimmy: You’re absolutely right. Joy is something that I struggle with. I think the reason I teach improv is so I can experience joy. I’m not somebody who laughs a lot. So maybe vicariously, the audience is teaching me how to laugh and how to have joy, as do my students when I teach improv. I put a lot of pressure on myself. I get in my own way of really having the best time I possibly can up there on stage.

Teme: As time goes on, are you able to feel more joy?

Jimmy: My daughter is going to be seven. She’s so super playful and silly. She’s also at that age where she’s becoming self-conscious and a little embarrassed. The other day, she said to me, “Dad, I don’t want you to take me to soccer because you make funny voices and you’re too funny.” But the playfulness of these years has really helped me because I’m very serious in real life. My wife Lauren and my daughter are much more playful than I am. I probably take comedy a little too serious at times.

Teme: That’s a reason I love comedy. I can be way too serious. I really need that outside inspiration to laugh.

Jimmy: You’re two or three steps ahead of me. When I watch comedy, sometimes it does make me laugh, but I’m so in my head analyzing what works that it’s very hard to lose myself in it. I would probably rather analyze something than laugh. That’s a serious problem.

Teme: Why do you think that is?

Jimmy: Laughter is letting go of control. When you can let go of that, you experience joy. Joy is something that I’ve tried to avoid my whole life. So it’s probably my protection against feeling joy.

Teme: Why avoid joy?

Jimmy: I never trusted joy growing up in my house. We grew up Catholic. If you had too much joy there was always fear. If you’re too happy, something bad is going to happen.

Teme: I recognize that. I’ve had a happy couple of months for whatever reason and I’m pretty convinced that means I’m going to fall down the stairs and break my neck any day now. So yeah, I totally hear that.

Jimmy: Also, feeling joy was like you were bragging. If you came home excited that you got an “A” – not that I ever got an “A” – you were bragging. We didn’t want to make other kids feel bad, so don’t talk about it.


Teme: Do you have a favorite story about being a dad?

Jimmy: I think one of my proudest dad moments is kind of a full circle thing. When I grew up, one of the things my dad taught us was to have good manners. When Betsy graduated from kindergarten, she got the Miss Manners Award. I thought, here’s something good that my dad gave me that I’ve been able to pass down to my daughter and we have a certificate that proves that. I felt very proud about that moment.

Jimmy Carrane/Photo by Jerry Shulman

Teme: What gift are you hoping to get on Father’s Day?

Jimmy: I asked for a weed wacker, so I think I’m officially a father. I’m not cool anymore. When you’re fifty-nine and have a seven-year-old, you let go of being cool. Not that I ever was, but I kind of thought I was. I always wanted to be popular and I always wanted to be famous. I wish I could go back. I’d be like, that stuff doesn’t matter! Just be as real as you possibly can.

Teme: You’re so right. Real is the best.

Jimmy: And it’s also the hardest thing to do because I want to look nice. I want everybody to like me. I don’t want to tell them that I’m hurt. I don’t want to tell them that I’m angry. I just want to be liked.

Teme: Yep. That’s my inner voice, too. Is there a gift that you would not like to receive on Father’s Day?

Jimmy: Being woken up at seven o’clock!

Teme: Do you and your daughter have any rituals that you especially treasure?

Jimmy: She’s very imaginative. She’ll create scenarios and sometimes it can get me in trouble. I’ll go along with it and will be like, “Yes, we’re going to get a pony!” Then Lauren will come in as the editor and be like, “You know you’ve got to tell her that we’re really not going to get a pony.” Once I’m in it, it’s really hard to break out of it. I’m getting better at that. Betsy’s like, “Yeah, I know he’s kidding.” She’s starting to pick up on that, and that makes me feel really proud because maybe she’ll get some of her comedy training from me.

Teme: Is your daughter on the road to becoming a comedian?

Jimmy: Well, I think we’ve screwed it up because we’ve given her too much love and attention to go into comedy.


Teme: I definitely want to let everyone know that tickets to World’s Greatest Dad(?) is a great Father’s Day gift! What else should we tell them?

Jimmy: When I was growing up, there was a lot of pain, there was a lot of anger and unexpressed anger, but there was also a lot of laughter, and that got me through a lot. So this show is going to be funny. Making my dad laugh was the greatest thing in the world and it’s something that I never outgrew. If you have a dad and you bring him and you get to laugh together, I can’t think of a better experience.

Maybe something in the show reminds you of something that your dad did that you want to thank him for. Maybe you’ll talk about the good things and the not-so-good things. There’s something healing in that. Through laughing there’s always a chance that you get closer.

Teme: That shared experience is really powerful.

Jimmy: Oh, yeah. Sometimes comedy shows can be one big inside joke that we’re all in on.

Teme: One of the most fun experiences in the world is being included in an inside joke.

Jimmy: Oh, my God, there’s nothing better than an inside joke. It’s like you’re creating a shared language. A comedy show is all about creating that community with the audience. It’s all about being connected through that shared experience.


World’s Greatest Dad(?) is at The Laughing Academy, 3230 Glenview Rd, Glenview on:

Friday, June 16 at 7:30 p.m.

Saturday, June 17 at 7:00 p.m. and 9:00 p.m.

Purchase tickets here.

All tickets sold out except for the 9:00 p.m. show on Saturday. I always recommend checking with the venue if you would like to attend a sold-out time. Sometimes additional seats become available.

More about Jimmy at jimmycarrane.com. I highly recommend his classes, blog and podcast.  

Jimmy was also kind enough to speak with me in October 2022 and June 2019.

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