How Jimmy Carrane became the World’s Greatest Dad(?)

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With his new one-man show World’s Greatest Dad(?), Jimmy Carrane will make it possible for Chicagoland to celebrate Father’s Day every Saturday night from June 15 through July 20 at Second City. The show brings Jimmy’s comedy and uncompromising honesty to a personal story that he’s revealing for the first time: his rocky, relatable path to becoming a dad at age 52 at the same time that his own complicated father was dying.

I can feel him recoiling now, but I’ll say it anyway. Jimmy Carrane is one of improv’s most renowned and best loved figures. He is willing to lay bare his offstage life and demons with a frankness that is both refreshing and rare. And hilarious. The result is always a profound connection with his audience. You cannot sit in a Jimmy Carrane show and feel alone. He is a comedy success story, but “I have a hard time hearing that,” he told me. While he may have doubts about his fame, his fans do not.  As Susan Messing said, Jimmy is “one of the funniest human beings on the planet.”

He is known for his “Art of Slow Comedy” classes and workshops which he has been teaching for over 25 years. Podcast and comedy fans also know him as the host of Improv Nerd where he interviews creative folks such as Key & Peele, Susan Messing, Rachael Mason, Kelsie Huff, Jill Soloway, Tim Meadows, Jordan Klepper, Cecily Strong, Rachel Dratch, Pete Holmes and even Top Chef Master Rick Bayless. Jimmy recently took a break from Improv Nerd, but fans will be happy to know that he was back in the studio last Monday recording the next episode with plans to release several more this summer.

Jimmy was also a popular host for seven years on WBEZ’s Studio 312, where his interviews included Jeff Garlin, Conan O’Brien and Cindy Crawford. On his roster of TV and film credits: Natural Born Killers, Early Edition and The Untouchables. His one-person show Living in a Dwarf’s House was a “Chicago Tribune Top 10 Show of the Year.”

Jimmy kindly spoke with me by phone about the real-life events that inspired World’s Greatest Dad(?), pain, and the unexpected healing power of parenthood (not that it’s all been easy).

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HOW IT ALL STARTED

Teme: Why comedy?

Jimmy: I was always funny as a kid. I lived on the North Shore and when I graduated from high school, I had no idea what I was going to do. Saturday Night Live was a show that really made me laugh and I didn't laugh at much on television. I don't laugh much in life, which makes it weird that I picked comedy. I knew Second City’s connection with Saturday Night Live so I started taking classes at the Player’s Workshop of The Second City in 1983. I was 19 years-old. When I found improv it was like everything that I had been shamed or punished for as a kid was now rewarded.

Teme: How so?

Jimmy: In school I was always a smart-ass and it got me in trouble. I was also the one who would call out things that were going on in the family and had a reputation for having a big mouth. But at Second City I realized, "Oh my god. I can use this in improv."

The big thing was that I came from a family where it was very hard to express myself. You weren’t allowed to express anger. Not being able to express anger turned out to be a great way to develop my sarcasm. Sarcasm was like a cousin of anger and I didn’t get in trouble for being sarcastic.

Teme: What happened as a kid when you expressed anger?

Jimmy: A lot of shame. I’d hear, "don't say that," or, "that's mean," or, "that's rude."

HOW TO FIND TRUTH IN COMEDY

Teme: One of the many great things about your comedy is your honesty. Does that honesty still ever feel unsafe?

Jimmy: Doing one-person shows brings up a lot of fear. It does bring up family stuff. I’m excited about this show and I'm also terrified.

Teme: How do you get past the fear?

Jimmy: A lot of therapy and a lot of getting help from people. It's a one-person show, but I have Gary Rudoren, a friend of mine who directed a couple of my previous one-person shows. He's helping me with the script. We did a preview last week and people gave feedback. What works for me is not doing it alone.

Teme: I’ve been to Improv Nerd and seen how you have an amazing ability to connect quickly on a profound level with your improv partner and with the audience. What's the secret?

Jimmy: Part of it is my improv training and my approach. And thank you for noticing. I teach a style of improv called “Slow Comedy.” I teach that you can make connections without any words being said. In improvisation, people often want to blurt something out and then they run over that connection. If you take a couple seconds and take in what's going on with your partner, you can connect with them very easily. The other thing is just my years and years of therapy have made me a little more empathetic and I think that helps too.

“WORLD’S GREATEST DAD(?)” IS BORN

Teme: How did you decide to do World's Greatest Dad(?)?

Jimmy: Three years ago, my dad was dying. We had a very complicated relationship. At the same time, I was becoming a first-time father at 52 years-old.

At the time, I had done some pieces about my dad and about my daughter Betsy being born. I thought, "I haven't done a one-person show in a long time. I'm getting a really good response. This would make a great show."

Teme: You mention that your path to becoming a dad involved both fertility treatments and a disastrous funeral. I don't want to ask you to give away too much of the show, but I’d love to hear anything you can say now.

Jimmy: Sure. Well, we went to three fertility doctors until Lauren finally got pregnant. That was a very emotional time. In terms of the disastrous funeral, I don’t want to give away too much, but my dad had asked me to speak at his funeral. He wanted me to get up and make people laugh, which was a real honor for me to do. But after he died, my brothers and sisters and my mom tried to prevent me from speaking at his funeral. It goes all the way back to not being able to express myself.

Teme: You’ve said that you were never interested in becoming a dad. What changed your mind?

Jimmy: I've mentioned therapy three times already, but I'm in group therapy and I was complaining about my career to my therapist. I'd been in group therapy for about ten years. I really got into group therapy just to be famous.

I don't mean to name-drop, but I will. I worked with people that went on to be really big: Chris Farley, Andy Richter, Rachel Dratch, Tim Meadows. Dave Koechner from Anchorman was a roommate of mine. Stephen Colbert and I did corporate videos together. I'd moved a couch for Mike Myers. Tina Fey and I shopped at the same convenience store.  So I was obsessed with being famous, and I really believed that fame was going to make me happy.

So I'm in group therapy and I'm miserable, miserable, miserable after ten years. Even though things in my personal life had gotten much, much better, I was still unhappy. I was fifty at the time and Lauren was thirty-six.  My therapist said to me, “If you want more joy in your life, you and your wife should have a baby.” Bringing more joy into my life is what spurred me into thinking about becoming a dad at that age.

Teme: Would you say that happened?

Jimmy: It didn't happen immediately. That's one of the things that I'd like people to take away from the show. Is it okay to say that? I always feel like it seems kind of pretentious …

Teme: No, in fact, you read my mind. I wanted to ask what you'd like people to take away.

Jimmy: One thing is that it's okay not to instantly love your child when they come out of the womb. I think it took me maybe eight months to finally start to have some unconditional love for Betsy.

There's this myth that, "Oh, once your child comes out you're just going to feel all this unconditional love." When I heard that, I felt like, "I must be doing something wrong." But that isn't the case.  My friends were saying, “Aren't you excited to be a dad?!" I was like, "No. It's hard and I'm tired. Why didn’t someone tell me this?"

THE BEST PARENTING ADVICE

Teme: You’ve said that you don't have to be the greatest dad to be a good dad. What should people know about that?

Jimmy: I’m a perfectionist which is probably pretty common in the comedy world. Before we were going to have Betsy, I was like, "I don't want to screw her up!" I got two good pieces of advice. One person said to me, "You're going to make mistakes. You're going to screw up. Just know that.”

The other piece of advice that was super helpful was from a friend of mine who has three kids and is a great dad. He said to me, "There're going to be days where you're like, "Oh my God, what did I do?" That was really helpful to hear because I was terrified before Betsy was born. I'm probably still terrified, but not as much.

PRE-DAD, POST-DAD

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Jimmy Carrane

Teme: How would you describe yourself before and after becoming a dad?

Jimmy: I didn't know this, but Lauren told me, "Before Betsy, you were really a depressive. You were really dark. Now it seems like you're less obsessed and more fulfilled." She was absolutely right. If you would've told me all that back when my therapist said, "You and your wife should have a baby because it will bring you more joy," I would've been like, "You've got to be kidding me!"

Teme: If you could go back in time, what would you tell your pre-parent self?

Jimmy: The same advice I would tell somebody starting out in improv: enjoy the process. Improv and having a baby are both scary because they involve fear of the unknown. I’d tell myself, "Hey, let’s have fun! It’s going to be great. You don’t have to freak out as much." I find it ironic that I teach improv which is about play and having fun. Even though I've been doing it for so long, I still teach it so I can learn to have fun from my students.

Teme: That’s great advice. I often forget that. I'm a bit of a doomster, so I sometimes feel if I let my guard down and have fun, something horrible is going to happen while I'm forgetting to be vigilant.

Jimmy: Growing up I learned that you don't trust fun. Just like you said, when you're having too much fun, something bad is definitely lurking around the corner.

Teme: What is the scariest thing about parenting and what is the most reassuring thing?

Jimmy: The scariest thing for me is that in parenting you feel all your feelings. It's like your feelings are on steroids. So you feel joy really intensely and you feel excitement really intensely. But you also feel fear and anger really intensively.

Last night, Betsy took a nap in the afternoon which is weird because she doesn't nap any more. She usually goes to bed by 8:30, but she didn't fall asleep until 11:30. As a parent, the anger and the rage that come out because you can't control this kid is like you've never felt before.

On the other end of the spectrum is joy. We went to a fair the other day and had the fun of her wanting to go into the candy castle. That joy is off the charts. If it were just you going into the candy castle you wouldn't experience the same thing. So it's those intense, intense feelings that are really scary.

The reassuring part of parenting - and improv has helped me tremendously in this – is that if you're adaptable in the moment with your kid, things are going to go much better. There have been times where we all got in the car looking forward to going out to dinner. Then all of a sudden, she's crying and our plan had to be diverted.

Improv taught me that there's not one way from point A to point B. You may initiate a strong premise, but you don't know where it's going and that's helped me in parenting. You’ve got to think on your feet because 50% of the time plans aren't going to happen because of the needs of your child.

YES, AND … IMPROV CAN HELP YOU GIVE YOUR CHILD A HAPPIER CHILDHOOD

Teme: Which improv principles work well in parenting and which don't?

Jimmy: The one that I love the most is mirroring. Mirroring is just doing what the other person is doing. It creates a connection with your child. When my daughter cries I'll go over to her and say, "Can I cry with you?" Sometimes she'll go, "Yes." Now that she's older, she'll say, "Adults don't cry. I don't want you to cry." But I found it really helpful to cry with her because it’s joining her just like you would do in improv. I found that when I mirror her, she wouldn't cry as long.

Teme: Oh, wow, because she felt heard and understood?

Jimmy: Yeah. The improv principle of "yes, and" also works in some areas, but sometimes you just have to say "no" and you have to set boundaries with your kids. So I would say "yes, and" can be used judiciously because it doesn't always apply.

Teme: Which improv principles do you want to teach your daughter as preparation for life?

Jimmy: Lauren said the other day, "When Betsy plays, she's very, very serious." And that's me. In improv I'm very, very serious. I haven't figured out that improv is fun. I hope she has some lightness when she's playing. I hope she has some lightness in her life. I think improv brings that. The one thing improv teaches is don't take yourself too seriously and I hope she gets that.

I’ve also noticed that when we go to the park or to a restaurant, she's most interested in watching the people. She's more of an observer and she's absorbing things. People think improv is verbal and you’ve got to be quick. But improv is listening, and listening is observing and taking things in. She's developing that skill, which makes me very proud.

IMPROV REFLECTIONS: DEL CLOSE AND MARTIN DeMAAT

Teme: What was it like to study improv with  Del Close and Martin DeMaat?

Jimmy: I was influenced by both of them very much. Del was a very intimidating personality. He was a bigger than life character and he had worked with all these famous people. I really wanted to please him. Del was like a father figure and I wanted his approval.

His classes were not touchy-feely and being supportive. He could be mean. But he was about truth in comedy. Del believed that you can just tell a story without embellishing it and get a laugh. I saw it work.

I studied with Del in the ‘80s. It seemed like there were only thirty of us improvising back then in Chicago. It didn't get much respect. When you said improv, people would be like, "What? Stand-up?" This is Chicago. We had Second City. You’d think people would know that. But they didn't. Del really made me believe that whatever I did as an improviser was an art form.

Martin DeMaat was such a kind, gentle improv teacher. I did some of my best work there because he made it so safe and supportive. Martin believed that improv was beyond just a performance. He believed it was a way to look at life. At the time I thought, "This is hokey. Let’s cut this crap out. I just want to be famous."

But the more I’ve taught improv, and certainly with having a kid, I see that my brain is wired like an improviser. For good and bad, I look at life through that lens.

Teme:  What's the good and bad would you say?

Jimmy: I look at everything as a collaboration. Everybody's ideas are good ideas and I need to take them. It can cripple me sometimes. Like when I got feedback from the preview of the show, I had to decide what resonated with me and what didn’t apply. The good thing is that you always get a better product when you stay open to other people's ideas.

AN HONEST APPRAISAL OF FAME AND HAPPINESS

Teme: If you were interviewing yourself what would you ask?

Jimmy: My question would be, “Why don't you think you're a success?”

Teme: How would you answer?

Jimmy: I don’t think I’m a success because of how I look at life. I want to focus on the negative. One of my biggest character defects has been, although it's certainly gotten better with having Betsy, is comparing myself to other people.

I would also say that the fame part of it has gotten in my way and fame isn't all you are. Lauren gets frustrated with me because I'm so obsessed with fame. She says, "We have this great relationship. You have a great life." Which I do. And she says, "Don't I make you happy?" And I'm kind of like, "Well … I don't know." I need to look at the positive. It's not all just fame and career. That's why I don't feel like I'm a success.  Also, as you brought up, I'm afraid of feeling joy.

Teme: What makes fame important? I think you are famous. But why did fame become something that was so large?

Jimmy: I looked at it like the Holy Grail. If I got famous, it would take care of a screwed up childhood and my low self-esteem. It would solve all my problems. I think our culture reinforces that. I think also I picked a field where when you see people go on to be famous. Every year I was in Chicago, somebody would go on to New York or Los Angeles. It was like I was being held back a grade again.

How I feel about myself is at the core of it. When I feel good about myself, it's not that big of a deal. But I'm not going to lie to you. If fame came to me, I would welcome it. But hopefully I'm not still as obsessed about it.

When I started out, a friend of mine, Tim O’Malley, used to say that as improv teachers we could really impact people in the classroom. As I started to develop, to become a really good teacher, I started to realize I am doing really good work and having an impact on the people in my classes and workshops. That’s helped me. I don’t think I enjoyed teaching the first ten years. Now later in my life, I really do enjoy teaching. I'm not part of a system, so I can teach the improv that I like to watch. That is really fulfilling. The most rewarding thing is when people in my classes go on and create their own shows. Often they’re still friends many years later. That's like being a proud dad right there.

Teme: So if you could have anything for a Fathers’ Day gift what would it be?

Jimmy: Oh my God. What would it be? A Fathers’ Day gift ... Well, I always appreciate money. Maybe a check for $10,000.

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“World’s Greatest Dad(?)” is at Second City’s Judy’s Beat Lounge, Saturdays at 6:00 p.m., June 15-July 20, 2019. Tickets here.

More about Jimmy at JimmyCarrane.com.

Sign up for Jimmy’s classes and workshops here.

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