Photo © Sam Willard

On Friday, November 18, Jimmy celebrates the 5th anniversary of Improv Nerd with a special show featuring Scott Adsit at the Chicago Podcast Festival. We asked Jimmy about the podcast, his career, and how to succeed in improv.

P&C: Congratulations on five years of Improv Nerd! When you started, did you ever think you’d do over 200 episodes?

JC: Never. I never thought that. At this point I thought that I would’ve been a really big TV star; someone would’ve said, “Oh my God, this guy can really interview people. Let’s give him his own show.” So I probably would’ve done 100 episodes and gotten a TV deal.

P&C: Like Marc Maron?

JC: I thought maybe like a talk show, or a radio show. It’s interesting, because if I would’ve known what I know now starting out, podcasting – podcasting has just exploded – I don’t think I would’ve done it. Because I really thought when I started out, it was me and Marc Maron and that was it, who were doing interview comedy podcasts. And the longer I did it the more I realised there is tons of podcasts out there, really good ones.

P&C: There is. I’ve had this conversation with friends, where you’re doing something and you think, “I’m gonna do this!” But then you see or hear something and you think, “I can’t now, someone’s already doing it!”

But no one will ever do exactly what you would, because your worldview is unique. So I’m glad you started at a time when you didn’t think, “It’s been done already,” because then we wouldn’t have Improv Nerd. Was it because you had a specific goal in mind, that you wanted a TV or radio show?

JC: Probably, it was a goal of mine. But certainly I thought I’d be in the top 10 comedy podcasts. I really thought I was going to be Marc Maron, that popularity, so that’s really what I was shooting for.

I know for me it’s really hard to do something and not expect certain results. I have certain expectations. That is the hardest thing.

P&C: You’ve interviewed so many amazing people: Key & Peele, Adam McKay, Jill Soloway, Mike O’Brien, Mick Napier, TJ & Dave, Susan Messing, Ilana Glazer & Abbi Jacobson, and Bob Odenkirk, just to name a few. Even reading that list is mind-blowing! Who was your favourite interview, and why?
JC: There were so many…Bob Odenkirk was one of my favourites because I was a huge fan of Mr Show. We did the interview and got really personal about his Dad and about Second City, and he talked about having this incredible feeling because he wrote the sketch for Chris Farley, the motivational speaker, and it was originally a sketch at Second City.

And he talks about just this great feeling. And at the end of the interview he said – I’m paraphrasing – “That was the most personal interview,” and then he signed his book, “Thanks for ripping my heart out.” And to me, someone who [I] idolised and really looked up to, because he’s mentored a lot of people, that just meant a lot to me.

The other one that – any one [interview] I could really talk about – but Dan Bakkedahl. He’s on Veep and Life In Pieces, and has been a friend of mine here in Chicago and I talk to him a couple of times a month. His interview was like the perfect episode. He was very honest and candid about his successes and some of the things along the way, like being on The Daily Show and what happened at Second City – I think he, if I remember, punched a hole in the wall because he was so upset.

And the thing is, he’s got great perspective on that. He is just one of my favourite improvisers to improvise with, and it was just so much fun. Because when you interview people that you know, it can be a little harder because you want to respect the boundaries; a lot of stuff that will get into your subconscious because you talk to them on a frequent basis.

Abbi and Ilana from Broad City impressed me. They didn’t make a Harold team at UCB, which is a very big honour and something everyone shoots for, akin to making the MainStage at Second City. If you get there, it’s a ticket to stardom. And they made their own path. And the other thing that impressed me about that was, I think it was the second season of the web series, before it went to Comedy Central, they took their own money and invested in the production. And I always thought – including myself, I need to learn this – if we all did that, how much farther would we be? They really believed in what they had.

P&C: I agree, it’s investing in yourself and believing in yourself, even when you don’t know if it’s going to be a hit. And it’s not like improvisers are walking around with huge wodges of cash, but if you do it for the love of it, it’s amazing where it can go.

When Shit Girls Say went viral, and then Shit New Yorkers Say, Ilana and her brother were in it, and I remember seeing, “Coming soon: Broad City, an Amy Poehler-produced web series.” So it started with one little video they probably made themselves for 20 bucks.

JC: For me, I’m obsessed with, “What is the secret?” with each of my guests; what has made them successful? Everyone has a different path, but I’m always trying to uncover, if I can walk away with one nugget or one tip on how to be successful – not that I’m going to apply it to my life (laughs) – but I feel like I’ve done my job.

P&C: Absolutely. I think everyone’s looking for shortcuts, or ways to avoid some of the problems, or whatever.

On that subject, you’ve been improvising for over 30 years. What advice do you have for someone who’s impatient because they’re not, either great at improv yet, or famous, and they’re in their 20s or 30s?

JC: I would say one of the biggest things is building relationships. So if you’re in a class, you’re already networking. Because here’s the thing: opportunities, or guests that have appeared on my show, Adam McKay or Jon Favreau or even Mike Birbiglia – not that I knew Mike, but he’s in my sphere so I could reach out to Brian Stack and say, “Hey, could you help me get him as a guest?” – all of that stuff comes from being a nice person, a kind person, and being someone who’s fun to work with.

I certainly in my 20s, probably 30s, and even my 40s, had an attitude, was a comedy snob, I still struggle with that. But if you can focus on the relationships, as well as having fun as you’re moving up the ladder hopefully, it’s going to pay dividends down the road. If you’re were a jerk, it’s going to be a lot harder for you if a friend gets a job, let’s say on a late night talk show, to reach out to him and say “I’m putting this packet together, can you look it over?”

I think the other thing is something I struggle with, and it’s constantly asking for help. I love it when people contact me and say, “Can you talk to me?” or “I just moved to Chicago,” or “I wanna move to L.A.” That stuff is invaluable, especially if people are successful and have done what you wanna do.

P&C: Some people might be intimidated, because they think, “Oh, so-and-so’s probably too busy,” or “We’re not on the same level, and who am I to approach them?” So you’re saying don’t feel that way.

JC: I’ll tell you, I wish I’d continue to ask more and more, because I have a very hard time asking. But there’s always going to be…for me, there’s more fear that they’re gonna say yes than that they’re gonna say no.

I love Jeff Garland. He’s one of my favourite people, one of my favourite performers. I’ve interviewed him twice for the podcast, and probably a couple of times for public radio. He’s always very generous with his time. He was doing a show at Steppenwolf and I had contacted his press person, and they said “Jeff’s only doing interviews on certain days, sorry.” The next day the press person contacted me saying, “Jeff didn’t realise it was you, he’d be happy to do it, he’ll give you 40 minutes before his show.” And I gotta tell you, I felt a ton of shame. I was honoured, but I called my [therapist]: “He’d do that for me?” And that’s the thing, that I think for me, not asking, I avoid.

I’m in therapy, I talk about it on the podcast, [he says] “You’re not afraid they’re going to say no. You’re afraid they’re going to say yes.” Because what I’ve experienced, there’s a lot more feelings that come up when somebody says yes. There’s a lot more feelings when you get “This might become a TV show.” There’s a lot of feelings with “You might get a part in a Judd Apatow movie.”

P&C: Is it feelings of “Do I deserve this? Am I good enough?”

JC: That comes up, but also sadness, like “Why didn’t this happen sooner?” Anger, like, how dare anyone recognize that I’m talented? It’s really hard, I was talking to a friend, she’s a great singer, her name is Meagan McDonough, and we were joking. It’s true, whenever you get close to your vision or your goal, you wanna quit. I don’t know what it is, but you just, like, “Uhh, I wanna quit.” And there’s been a lot of times where I felt like I’ve gotta quit, and I’ve done it. And now I know, that’s just part of it, that’s just part of my process.

P&C: Having the self-awareness to recognize that. I think Cameron and I have, just from being on the planet longer, we’re getting better at “Oh, I can see this pattern with me,” or this self-defeating behaviour.

Which dovetails into my next question: What have you learned, personally or professionally, from talking to these 200 or so people?

JC: I think the hugest lesson – and I was talking to my wife Lauren before the interview – I thought that everybody thought like me, which is, “Fame is the most important thing.”

And the thing that I’ve learned is, there’s a lot of people doing improv, a lot of very accomplished improvisers and teachers that really aren’t obsessed like I am about fame.

P&C: Did that surprise you?

JC: Yes, it totally surprised me. As an interviewer, just like as an improviser, you’re bringing your life experience and your point of view and your obsessions to the interview. It leaks out.

Growing up in Chicago around Second City, and seeing so many people that I started out with going to New York and Los Angeles and becoming huge in TV and film, I always thought you got into it – not that I originally got into it to be famous, though on some level I probably always wanted to be famous because I thought that would make up for my low self-esteem – but that that was the end goal. And to see people not only in Chicago, but to travel around and go into smaller cities and see these people that are creating these great improv and comedy theatres, and the work is really, really good, and that they’re super happy doing that, it really did surprise me.

P&C: Improv and comedy – and really, the world – is going through a sea change in 2016 with regard to awareness of and treatment of women, and also people of colour. Do you see things moving in a better direction now in the improv community?

JC: It’s hard for me to really give that perspective because I’m a white male. I would say that bringing it to the surface, that’s gone on for the last year, is really helpful. I consider myself a pretty sensitive and pretty compassionate person, and I think it’s helped me become more sensitive to these issues.

P&C: I was talking to Susan Messing about your episode on the subject, and I thought you handled it really well, even though you’re a guy (laughs). It’s a tough thing; we’ve got similar issues in Canada, and I’m sure England and Australia are having similar conversations…and this was all before Trump. (laughs)

JC: That episode…I was really afraid. It was a very angry time, and I was afraid that I was walking into something… I thought everyone handled it so well, and people’s points of view came across. Being a white male it’s not my issue to talk about. I can’t speak from experience, but I can give people a platform to discuss it. Hopefully the discussion keeps going.

P&C: When you started the podcast, there were very few improv resources available. When Cameron and I starting improvising, there was Truth in Comedy, your and Liz Allen’s book, Mick Napier’s book, and that’s pretty much it. Now there’s this plethora of podcasts, new books, blogs, e-books, improv camps, new theatres cropping up in small towns that never had that kind of thing before. Do you think having all these resources is making better improvisers?

JC: Yeah, I think it is. I will get someone contacting me periodically from somewhere in Europe, let’s say a very small town in Ireland, and they’ll say “Thank you so much for Improv Nerd, because it’s like getting a Master Class.” I think being in Chicago or any major city that has a lot of access to teaching, we probably don’t think of it as much, but there’s so much going on in Europe.

I do intensives in the summer and I get a lot of people coming to Chicago to take Second City and iO, and then they’ll study with me, and I’d say most of my students in the summer are from Europe. And what’s interesting is, Europe is like what Chicago was when I started back in the ‘80s. Will Hines has a book and Paul Vaillancourt has a book and Mick Napier just wrote a new book, and I think this is really good because [it helps] people in different countries where they don’t have access to the kind of training we have in big cities.

P&C: We all know improv has exploded in popularity, especially the past five years. Do you think it’s possible to become too popular, in terms of stage time and opportunities?

A friend of ours auditioned for a Harold team recently and he was number 600-and something. I thought, wow, you’re one of 600 for a chance to audition to maybe get on a team. And I guess that’s the reality because there’s so many people now vying for a place. So my question is, how big can this get? Are some people going to get frustrated because they think “I’ll just never have a chance”?

JC: If the improv community gets bigger, if you’re number 626 and you audition and you don’t get in at one of the big institutions and theatres and schools, that doesn’t mean you’re not good. We mentioned Broad City; they didn’t look at UCB as their gatekeeper, they created their own thing.

There’s so many people that I’ve had on the podcast who’ve said, “Once I gave up wanting to get into Second City, the opportunity presented itself and I got in to Second City.” So, when I hear that I think, that’s a lot of people doing improv, doing comedy, and I hope that just because they don’t get in there that they give up.

What I’ve seen since I’ve started is that people have become a lot more savvy. Here in Chicago, it used to be that people would do three or four MainStage shows. Now if somebody does two MainStage shows that’s a big deal, because they already have representation in Los Angeles, a manager and an agent. There’s people in Touring Company at Second City that are being scouted and are getting managers and agents. So it’s really changed.

When I started, if you were thinking about going to L.A. or you were going to get a headshot and do commercial auditions when you first started out, you were selling out. Del really preached an artist mentality, and a lot of us took it to heart, for better or for worse.

The other thing I think is interesting, because I not only come at it as an improviser and a performer, [but] as a teacher: I have seen the teaching side of it, not only here in Chicago – iO has exploded in terms of its training centre, the Annoyance, Second City just did a 25,000 beautiful square foot expansion of their training centre; there’s other theatres like Under The Gun, and Kevin Mullaney and Bill Arnett and Dina Fackliss teach independently here in Chicago, which is really super encouraging, and I of course teach here in Chicago – so that movement’s going on. But also what’s going on as far as corporate. I do it for team building, [how to] be more creative. I’ve seen it with doctors, people teaching doctors how to have better bedside manner. Or social anxiety… So the teaching aspect probably is endless in terms of where people can take this.

P&C: That’s a really good point. Cameron teaches Play Anxiety Away. A lot of students don’t necessarily want to be improvisers, or perform onstage. But some of them fall in love with it so much they end up going through the regular Second City program and even Conservatory. And others are like, “I just wanna be able to leave my room without breaking into a cold sweat,” which was Cameron’s story. The diversity of classes available now is probably tenfold what it was a decade ago.

JC: When I go and teach workshops across the country, I’m seeing a lot more people coming to improv later in life. And that’s where it’s like, they don’t care about being famous, they don’t care about getting the writing job on The Daily Show. They’re doing it because they want to express themselves, and they want to be part of a community.

The two greatest things about improv is, one, it’s very accessible, anybody can do it, and two, you feel like you’re part of something, even if it’s a class of 12 people, you feel like you’re part of a community, something bigger than yourself.

P&C: Totally agree. OK, last question: What does the future look like for Improv Nerd and/or for you outside of that?

JC: Oh, God…

P&C: No pressure.

JC: Well, every 10 years I do a one-person show. My first show was called I’m 27, I Still Live At Home and Sell Office Supplies. So I’m hoping to start to work on that. I have a lot of material from my daughter, who just turned 16 weeks, and the whole experience. So I don’t know what the show will be about, but I would love to do that.

As for Improv Nerd, I did go out [to L.A.] in the Spring and try to pitch it, and I got some interest about it. It would be great if someone would just turn it into a TV show and I’d get eight episodes and get the biggest names in improv and it would be on Seeso… That would be great because I love interviewing people. So, I don’t really know, but that would be my vision.

P&C: Thank you for speaking with us, and for doing Improv Nerd and putting your passion out there, because it’s inspired a ton of people. And I also want to give a shout-out to your blog, because your blog fucking rocks. I love that you express things that I think many of us have felt at one time or another. Love your writing, love your honesty, so thank you.

JC: Thank you.

Jimmy Carrane is an improviser, interviewer, teacher, author, and long-time member of the Chicago improv community. As creator and host of the Improv Nerd podcast, he’s interviewed just about everybody in the comedy cosmos. He has written three books on improv, and his blog is a must-read for improvisers.