My Fondest Memories of my Improv Career

This past week, I was working really hard and feeling depressed, because I felt like my work wasn’t getting me anywhere. So I went on Facebook to try to feel better.

And it didn’t work. It made me feel worse. Everyone I knew was posting about some part they had just gotten on a TV show or some amazing press they were getting, and all I could think about myself was that I haven’t really accomplished anything, I’m not famous, I suck.

But yesterday, my wife, Lauren, suggested I make a list of the five improv shows I’m the most proud of, and as I thought about it, I realized I have a lot to be proud of in my improv career. I hate when she is right, and I know that if I want to grow, I need to appreciate what I have done, instead of always beating myself up for what I haven’t….blah, blah, blah.

So today I’m going to tell you about some of my proudest moments in improv, and I’m going to trust that by talking about them, I will start believing that maybe life is going ok.

1. I’m 27, I Still Live at Home and Sell Office Supplies — Annoyance Theater
I have never had a bigger hit than my autobiographical one-person show — a brutally honest and humorous look at what happens when an ungrateful child moves back home with their parents and they fight about whose job is it to buy Diet Coke. The show was directed by Gary Rudoren, and critics loved it.  It played to packed houses for a year and half at The Annoyance Theater back in ’90s.

Fondest Memory: I was fat when I did “I’m 27…”, like around 270 pounds, and one night, ten minutes into the show, I spilt my pants right down the crouch. I panicked. I couldn’t leave the stage, instead I told the audience what had just happened and took the cardigan argyle sweater I was wearing and tied it around my waste like an apron and continued on. That night, I became a professional.

2. Jazz Freddy– Live Bait Theater
What a cast. What a time. Jazz Freddy was a long form group consisting of Pete Gardner, David Koechner, Brian Stack, Kevin Dorff, Noah Gregoropoulos, Miriam Tolan, Rachel Dratch, Pat Finn, Susan Karp, Stephanie Howard, Chris Reed and me. We were all young and hungry and we had something to prove. We all shared Pete’s vision of doing a slower, more thoughtful long form show in a theater and we ended up influencing a whole generations of improvisers who followed.

Fondest Memory: Years after Freddy had ended, I was at a press screening for the film Elf and was talking to the director, Jon Favreau, who by now was super famous. We were in a conversation, and this short little guy with thick Coke bottle glasses kept lurking around, and I thought he was waiting to get Jon’s autograph. After a couple of minutes he interrupts us and looks at me and says, “I loved Jazz Freddy,” and darts off. I felt proud and then embarrassed that he recognized me and not Jon.

3. Naked – iO Chicago
Stephanie Weir is hands-down one of the best improvisers and most talented people I have every worked with. The show was probably one of the first duo improv shows around at the time. It was just Stephanie and I, improvising one long relationship scene for one hour. It was Rob Mello’s idea and he directed both of us in it. She was brilliant and so easy to perform with. I wish that show would have gone on forever.

Fondest Memory: I was angry person in those days, much more angry than I am today, and I had been super jealousy of Stephanie’s talents, although I was unaware of it. My jealousy was coming out sideways during the show, and I was always making angry choices in my scene. After one show, Rob and Stephanie confronted me about it in the green room, and though at the time I felt a huge amount of shame and felt like they were ganging up on me, they were 100 percent right. Sometimes your fondest memories are the ones you learned the most from.

4. Godshow — Second City ETC
Godshow was Tim O’Malley’s show about redemption and recovery. It was a Second City review-style show about Tim’s life. He was the main character and narrator, while the four of us in the cast got to play multiple characters. I loved the story, and recovery is something close to my heart. Norm Holly directed, and I had been telling myself for years that I couldn’t do characters, but in this show I shined doing a wide range of characters – everything from a junkie, to a black woman to a British director to God himself.

Fondest Memory: One of the characters I got to play in the show was Martin DeMatt, one of my favorite improv teachers. Martin had died a couple of years before, and people who knew Martin said I was channeling him in the scene. One night before the show, Tim told me that Patty DeMaat, Martin’s sister, was in the audience. I was terrified. How was I going to play him? I didn’t want to offend her or have her think I didn’t respect him, so I dialed it down, a little less Martin, if that is even possible, and I remember briefly speaking to her back stage about it and she seemed really honored by what I had done.

5. Pent – iO Chicago
I was asked to join the cast of four improvisers for this long form show at iO that was started by Dan Bakkedahl. We would rehearse one hour before the show and Dan would show us a couple of moves and techniques from “Four Square,” a great long form show that he had been in. I used to always feel a little in my head whenever I played at iO, until Pent. It was so much fun rehearsing and improvising with these people, and I was sad when Charna broke us up. I performed with an all-star team after that for a short period of time, which was fun, but not like Pent.

Fondest Memory: There’s isn’t one show or rehearsal that sticks out in my mind. Instead, I remember the overall experience of the form and how it created a sense of freedom I had never experience in improv before. I also learned a valuable lesson when Charna broke us up. At the time, I was in my early 40s and was also teaching at iO. Pent was made up of all A-lister improvisers, and I learned that Charna’s decision had NOTHING to do with talent, and I’m glad that I learned that lesson, even late in my life.

Want to study with Jimmy Carrane? Jimmy’s next Art of Slow Comedy classes start April 12 (Advanced) and April 14 (Intermediate). Plus, he has a Two-Person Scene Tune-Up workshop on April 5! Register today.