Of Fathers and Fame and Jimmy Carrane

I don’t know how we got home from Elgin. It was a long drive, but all I remember is my husband and me, immersed in an altered state discussing Jimmy Carrane’s World’s Greatest Dad(?).  We were returning from this year’s Elgin Fringe Festival where we’d seen Jimmy’s reboot of the show he first launched in 2019 at Second City. Back then, you were lucky to get tickets before they sold out. Same thing now, and you’ve only got two more opportunities: October 16 at Mrs. Murphy’s & Sons Irish Bistro in Chicago and November 23 at the Metropolis Performing Arts Centre in Arlington Heights (links below).    

At the Fringe, with only a chair and a lectern, Jimmy took a rapt audience behind the scenes of one of the most transformative periods of his life. The forty-five minute show, which was punctuated by frequent applause breaks and laughter, can only be described as comic storytelling perfection.

Jimmy is an original member of the Annoyance Theatre and of the Armando at iO Theater. As an improv teacher known for “The Art of Slow Comedy,” Jimmy instructs students worldwide. As an interviewer formerly for WBEZ and now with his own podcast Improv Nerd, Jimmy has interviewed Conan O’Brien, Susan Messing, Rachael Mason, Joey Soloway, Jeff Garlin, Tim Meadows, Cecily Strong, Key & Peele and many more.   

In World’s Greatest Dad(?), Jimmy tells his own comedy origin story. He started out in Chicago improv in the 1980s with people who rocketed to fame – Tina Fey, Stephen Colbert, Mike Myers and Andy Richter to name a few. He roomed with David Koechner (Anchorman, The Goldbergs). To Jimmy, fame seemed like a magic elixir, the thing that would fix childhood trauma and a pervasive sense of invisibility. Still, fame eluded him. Bitterness, self-loathing and therapy ensued. The therapist’s surprise advice? Get married. Have a baby. Did Jimmy follow through?

The title of the show reveals only a fraction of the answer. World’s Greatest Dad(?) covers a series of events that would drastically change Jimmy’s perspective. Marriage and fertility treatments collided with the death of his complicated father, a harsh workaholic lawyer and real estate developer who was convicted of embezzlement. At his dad’s funeral, Jimmy saw the potential for a healing moment and planned a heartfelt eulogy, only to be thwarted and pounded back into silence by his family and the Winnetka police.

Jimmy says that he can be “a depressive guy,” but he is unparalleled in his fearless authenticity and ability to extract comedy and insight from this roller coaster we call life. His performances are so powerful – and funny – that I, just as an audience member, in less than an hour, emerged emotionally healthier. Jimmy’s story is riveting and liberating. When you hear it, you understand that there are multiple ways to interpret your life and there is always the potential to begin your own transformation now … or on October 16 or November 23.

Jimmy’s comedy is therapeutic for his audience and students, but is it therapeutic for him? And why did he decide to rewrite World’s Greatest Dad(?) now when it was already a hit? Will he finally take credit for his contributions to improv comedy or is he still plagued by feeling “not enough”?  Jimmy kindly spoke with me by phone to answer these and other questions about how he finds the comedy in healing and the healing in comedy.  

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A COMPELLING RE-LAUNCH

Teme: Why did you decide to rewrite and re-launch World’s Greatest Dad(?) this fall?

Jimmy: I originally did two runs at Judy’s Beat Lounge at Second City three years ago. But I wasn’t done with the show. There were parts of it where I was like, “This could be funnier or this part could be even better.”

Teme: What didn’t feel done?

Jimmy: Well, it just changed so much. The beginning didn’t feel right to me, so I’ve worked a long time on that and I actually took some standup classes. I decided to mix a little bit of standup with storytelling at the top of the show. I wanted a lighter, fun tone at the beginning because I could be a dark and depressive guy.

Teme: Which parts were hardest to write?

Jimmy: Anything around my dad was difficult. Even performing it, I always leave a little sad, a little melancholy. But again, I’m a depressive. But rewriting it this time I found that I had a lot more similarities to my dad than I thought when I originally put it up. I had a lot more compassion and in a weird way, I feel closer to my dad and he’s been gone now for six years.

Teme: You read my mind! My next question was whether the show transforms your relationship to your dad?

Jimmy: It definitely does. As I said, I feel closer. There’s one part of the show and it’s a small part, but it’s when I read the “good list,” the positive stuff that my dad gave me. My dad’s response was always, “Don’t read your damn list. We all know it’s bullshit.” That’s when I realized that I have a hard time taking in good things about myself.

The other big theme is that my dad didn’t feel good about himself the same way I didn’t feel good about myself. I was searching for something outside myself to make me feel good about myself. I think that’s something that I had in common with my dad.

Teme: Has your family seen the show?

Jimmy: No, my family has not seen the show.

Teme: Would you want them to?

Jimmy: I don’t know. I have mixed feelings about it. There’s part of me that would want them to see the show and see how much I loved my dad and to understand me more. And then there’s a part of me that’s thinking, “Oh, they won’t get it.”

A RARE QUALITY

Teme: The mark of a great show is you can’t stop talking about it. Jeff and I were talking about your show all the way home and beyond. You have a ton of insight about success, purpose and love. As I was thinking about it more, I thought that healing is also a major theme and that you are a healer with your comedy – for yourself maybe, but definitely for your audience. Would you agree?

Jimmy: Certainly I love the compliment. So I’ll take it. If I can get to the place where I can laugh about myself, not necessarily in a self-deprecating way but I can laugh about, say, one of my character defects, then I know I’m on the path of recovery from it. When I’m writing, I’m thinking that if I can find that truth and make it funny, it will help me and hopefully it will also help the audience.

Teme: Was that your intention in writing this show?

Jimmy: No, I think I wanted to tell the story. This all happened in a year’s time. The funeral scene with my family, which is one of my favorite scenes to perform, was such a traumatic experience. Then a couple months later we have a baby. There was so much there to talk about. There was a long period of time when I didn’t feel like I had much to say. But after that passed, I had stuff to say for at least the next four or five years.

Teme: What makes comedy a good conduit for working through hard things?

Jimmy: For me, I need to get distance. That’s really important. I did a show about my dad going to jail and the whole courtroom scene, but it wasn’t the time to do it. I don’t think he had even been sentenced yet. I was still very angry and I had a lot of resentment. I put that [show] up, but I couldn’t find the funny.

So for me, it’s having distance on it and then getting help around it. In this show, I talk about my therapist, but it could also be recovery groups or friends and talking about it and processing it. Once you can laugh at it you see, “Oh, I am a control freak.” Or “Oh, I am passive aggressive.” Then I can go on a stage and admit that and have people laugh because I’ve come up with something that’s funny. To me, that’s like two years of therapy right there.

Teme: There’s something about laughter that’s so validating while also fostering connection.

Jimmy: I talk about it in the show. I got validation and attention from my dad by making him laugh. And then that became my role in my family. Then it became my role in life. And then you’re constantly seeking it. It can cause you problems like it has for me before. But there also is this feeling that if you can make people laugh about dark subjects and stuff that you’re embarrassed about, it can give the audience permission to laugh at themselves, I hope.

Teme: It’s so good as an audience member to realize you can laugh at hard topics and that I don’t have to pull myself down into the depths.

Jimmy: It’s been an asset and also a liability. I had a very dysfunctional childhood. I had a lot of trauma in my childhood, but being able to laugh got me through it. On the flip side, it’s sometimes a great way of not dealing with your feelings and being a little closed off. So it’s finding that balance, I think, that I’m trying to do in this show.

STARTING OUT IN IMPROV

Teme: How did you first end up at Second City? What was the moment that you thought, “Oh, this looks promising?”

Jimmy: When I was in high school, I went to see a Second City show with friends. I remember thinking that it looked like a lot of fun. Then I graduated from high school. I grew up in Kenilworth and went to New Trier, and basically cheated my way through high school. I was not a good student and I didn’t go away to college. I was feeling tons of shame. I think I wanted to do it just for my self-esteem, so I could tell people that I was taking classes at the Players Workshop at Second City.

I struggled because I was young. I was eighteen and the other students were in their twenties. I was always the youngest kid. But I really found my place. The fun of it and the people kept me going.

THE ART OF SLOW COMEDY

Teme: How did “The Art of Slow Comedy” come to you? What was missing from improv and needed to be addressed?

Jimmy: TJ and Dave are masters of slow comedy. I always loved them. I started taking improv classes in the ’80s. I never liked the fast, “Let’s be funny!” approach because that wasn’t my kind of humor. I always loved the slow humor. I started teaching it because each generation seemed to want to go faster and faster and faster. I wanted to teach the kind of improv that I like doing.

People say to me, as if I invented it, “Oh my God, this is the greatest thing.” I think it’s because they don’t have to be funny. They don’t have to be witty or clever. They just have to react to their partner. Then what happens, especially with people who come to improv later in life, is they’re tapping into their emotions and their life experience without even realizing it.

Teme: Does “The Art of Slow Comedy” have healing properties? I feel that you added something important to the Chicago comedy scene with your approach.

Jimmy: Improv is not therapy, but it definitely can be very therapeutic. I’ve been teaching the “Art of Slow Comedy” for 20 to 25 years. Five years ago, I was interviewing Sam Wasson, the author of Improv Nation. I asked him, “What’s your favorite kind of improv?” He said, “I like improv where it’s very slow because you can feel your emotions.”

Here I had been teaching all this time and I hadn’t realized until that moment how it worked. I think, Teme, improvisers get on stage and we want to talk. But by slowing down, we’re actually connecting with that other person at an emotional level. We may not know it, but tapping into your emotions is where the healing appears.

Teme: What has been the most memorable student breakthrough or transformation so far?

Jimmy: Oh my God, there are so many. I was teaching the “Art of Slow Comedy” at Second City. I had a student who was really quiet and introverted. He finished level one and I thought, “Well, I don’t think this guy’s going to do it. I don’t think he got it.” So then he does the second term. And that guy just blossoms. I don’t know what it was. I can’t explain it, but he just got it. You never know in improv when people are going to get it and when people aren’t. To be honest with you, Teme, I don’t think I really got improv until probably the last five years. And I don’t think I understood teaching – and then I got really, really good at it the last three years.

A DAUGHTER’S INFLUENCE

Teme: You’ve said that improv influenced your approach to parenting.  How has parenting informed your approach to improv?

Jimmy: What I’ve seen with my daughter is her ability to play. She goes from one thing to the next very quickly because children have short attention spans. They’re not interested in doing it “right.” Sometimes I’ll be like, “Well, wait a second, Barbie should be doing this.” But my daughter doesn’t care. She’s created her own universe. The question is, can I play in that universe?  With teaching, that translates into shutting up and allowing students to play more. That’s really the big takeaway. And also – and this took me a long time and I still struggle with it – to meet the students where they’re at. My approach to improv needs to sometimes be in the back seat.

Teme: You must see your daughter responding and thriving as a result of your insights and avoiding the destructive messages that kids too often get.

Jimmy: Yes. I’m very conscious of that. I’m not a perfect dad by any means. I mean, yesterday I got mad. This weekend I got mad a couple times. It was very interesting. Actually, the other night I got mad at her, and she said, “Daddy, I was mad at you.” And I said, “Thank you, Betsy, for telling me.”

In my house growing up, you couldn’t get angry or you could get angry, but you got shamed for it. I couldn’t express myself. I’d like to do something different for my daughter. I think that’s what got me to improv. It let me express myself. I didn’t know that was why I was doing improv when I was 18 years old. Everything that I had gotten punished for or in trouble for saying was now being rewarded in improv. I was with like-minded people. I’m sure a lot of them had the same kind of parents that I did.

Teme: I think one of the worst things about adulthood is your mind gets so cluttered by rules and expectations. Things that get in the way of joy or just experiencing life. Kids are so much better at that.

Jimmy: And you brought up how doing the shows is healing. I really feel like teaching improv for me is healing. Deep down, I’m a very rigid person, very controlling and risk averse and fearful and filled with anxiety. I think we’ve covered it all in those five. Improv and teaching improv is healing for me because I have to let go of those things and be good at it.

NO SHAME IN THAT FAME

Teme: Fame comes up as a big theme in your show. Why was seeking fame so important? What did you think fame would solve?

Jimmy: One was low self-esteem, low self-worth. It goes far back. Growing up, I felt invisible. I was one of five kids and I didn’t feel that my parents saw me. So that’s one thing that I’m certainly dealing with.

The other thing, and this comes out in the show, is that my dad was somebody who wanted to become famous as a big real estate developer. Have a building with his name on it. So what I learned was the only way you’re going to get self-esteem in this world is if you accomplish something outside yourself. Those would be my two votes on why fame has been so important to me.

Teme: Have your feelings changed? Does fame still feel necessary?

Jimmy: It doesn’t. Again, the healing aspect of this show … When I first started this show, I’m not going to lie to you, I was like, “I hope I get a Netflix special. I hope I get a TV show. I hope I’m famous from this.” But now, getting to rewrite the show, I’m in a different place.

The ’90s in Chicago was an amazing time. One out of four people was becoming famous. It was Stephen Colbert and Carell and Chris Farley and Mike Myers. Later it was Bonnie Hunt, Amy Poehler and Tina Fey.  I mean, it was always there and it was very hard not to compare yourself. I’ve gone to smaller markets to teach and I don’t think they have that same thing that Chicago has- if I wasn’t famous, I was a failure.

Getting married, becoming a father, really changed that. There’s something about a child that switches your focus and fulfills you in a way that I never thought. And also constantly working on myself. Sometimes the same feelings, although it’s not as bad, will spring up. I’ll see somebody, one of my friends get something and I’ll be like, “Ah, I’m such a loser.” But now it’s like, okay, it stings a little, but it doesn’t control my life like it used to.

Teme: I think it’s human to feel that way. But you are famous. A lot of people go through Chicago comedy, but not a lot of people change and elevate Chicago comedy. You’ve done that.

Jimmy: Well, thank you. It’s hard to see, but I appreciate that.

TAKE-AWAY

Teme: What do you hope audiences take away from World’s Greatest Dad(?)?

Jimmy: When I put the show up the first time, people came up to me to share, “My dad did some sketchy things. He didn’t get caught.” Or, “My dad got in financial trouble and he actually killed himself.” There was so much shame. I was floored by that. I still feel some shame about my dad going to jail, but I also realized that this show has been more helpful to others than I thought.

I hope audiences will look at their relationship with their parents. I have a complicated relationship with both my dad and my mom and I’m still working on it. But there’s a taboo around saying that. I hope people will look at their relationship with their parents and see both the good and the bad, and not just the bad.

I’M ENDING WITH A QUICK MASTER CLASS

Teme: You are one of my all-time favorite interviewers. What is your advice for doing great interviews?

Jimmy: Wow. I don’t think I’ve ever been asked that question and I’ve always wanted to be asked. I’m going to give you a couple of points I’ve always wanted to share. First is to listen. It’s the same principle in improv. A lot of times I’ll write out questions and then I’ll ask the question, but then all of a sudden something will spur me to ask a different follow-up question. You may think “Oh, that’s not the second question that I’ve written out!” Go with your instincts.

Second, reveal something about yourself so the guest feels comfortable revealing something about themselves. You don’t have to go into it for a long time. Sometimes I think in these podcasts people make it about themselves. I always think it’s about the guest.

And getting back to instinct, trust your instinct. If you have passion about something, if you’re curious why Happy Days was shot on film in the first season, and then it went to a live audience, ask that question. You can always edit. But if a question means something to you and you’re excited about it, that’s how your personality comes out. And it’s different from everyone else’s. 

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Tickets for World’s Greatest Dad(?):

Sunday, October 16: Mrs. Murphy’s & Sons Irish Bistro, 3905 N. Lincoln Ave., Chicago, 3:30 p.m. Tickets: $15. Purchase here.

Wednesday, November 23: Metropolis Performing Arts Centre, 111 W. Campbell St., Arlington Heights, IL, 7:30 p.m. Tickets: $30. Stage tables $35. Purchase here.

Stay up to date with Jimmy at jimmycarrane.com.

Listen to Improv Nerd here.

Take a class with Jimmy and sign up here. Jimmy will continue to offer classes in person and online.

See Jimmy in the new Apple TV Plus series Shining Girls.

Jimmy and I spoke about Jimmy’s career and World’s Greatest Dad(?) in 2019 here.