My Top 10 Moments of 2016

Well, 2016 is almost over, and I want to thank you for all your support and encouragement over the last year. As you know, it’s hard for me to find joy in most things that I do, but when I take a look back at this year, even I am impressed with all of the incredible things that happened.

Here are my top 10 highlights of 2016:


  1. On July 2 in the afternoon, the most beautiful little girl, Betsy Jane Carrane, was born, making me officially a father. Now she’s almost six months old, and we have already given her six different nicknames. I love that little “Chunko” so much.
  2. In March, my father died. I was fortunate enough to have made amends with him before he died, and I got to say goodbye to him on his last day on this earth. I said I loved him. Lying in the hospital bed, he could not speak. He just raised his shaking hand to communicate that he loved me too, in one of the most intimate conversations I have ever had with him.
  3. With the support of Lauren, I went to Los Angeles in April to attempt the impossible and to try see if I could sell the podcast Improv Nerd as an actual TV show or as a web series on a digital platform. I had tons of meetings with executives and recorded five episodes of Improv Nerd in Feralaudio’s state-of-the art studios. Instead of being completely scared, I was actually excited and proud of myself for showing up, and so grateful for all of the support I got from friends who are “in the business.”
  1. While in LA, I was a guest on Dan Harmon’s popular podcast, HarmonTown. What was only scheduled to be a short appearance lasted almost an hour, and working with Dan Harmon and the rest of the guests was a complete blast. I really felt like a star.


  1. In January, I got to travel to Austin, TX, one of my all-time favorite cities for food, people and improv. While I was there, I got to teach improv workshops and do shows at The Institution, a theater run by Tom Booker, one of my old friends from my Annoyance Theater days.


  1. In March, I had the opportunity to travel to Pittsburgh’s growing Arcade Comedy Theater, where I taught improv workshops and interviewed and performed with Kristy and Jethro Nolen, whom I knew and loved back when they were here in Chicago. Pittsburgh is a surprisingly cool city, and it was so much fun reconnecting with Kristy and Jethro and seeing how much the improv scene is growing there.


  1. In August, I had the chance to travel to Miami, a city I had never been to before, and teach and do shows at The Villain Theater and interview Jeff Quintana for an episode of Improv Nerd. It was the first time I traveled after having the baby, so it was hard to be away, but it was also fun to feel single again.


  1. In September, Improv Nerd turned 5 years old, and we celebrated with an amazing show at the Chicago Podcast Festival in November with special guest Scott Adsit. The show was in front of a big crowd at the Athenaeum Theater, and it was awesome to work off the energy in the room and play with Scott, who had some great stories to share, including one about me from college when Martin DeMaat called me a “log.”


  1. This year really marked an increase in the number of big guests that I was able to get on Improv Nerd (partially thanks to Lauren pushing me to do more phone interviews). I got to interview some of the biggest names in comedy including Cecily Strong, Jane Lynch, TJ Miller, Mike Birbiglia, Jon Favreau, Jon Glaser, Jason Winer, Simon Helberg, Nia Vardalos, Kevin Nealon, Nora Dunn and Hello From The Magic Tavern.


  1. I also had a great year teaching some of the most talented improv students in Chicago. I am humbled and grateful for the level of students I had in my classes and improv workshops this year, all of whom learned how to challenge themselves, each other and me. Oh, and it was pretty cool that my Art of Slow Comedy summer intensives completely sold out, mostly filled with students from around the world. I’m international, baby!

What were some of your best moments of 2016? Tell us in the comments below.
Want to start off 2017 right? Sign up for Jimmy’s Art of Slow Comedy Level 3 class, starting Jan. 4. This class features a performance on the last day of class. Only 2 spots left!

My Top 5 Favorite Moments of Improv Nerd So Far

This September, Improv Nerd turned three years old. At this point, we have recorded 106 episodes. Over the past three years, I have gotten to improvise with and interview some of the greatest comedy minds out there today. And lately, I’ve been traveling across the country, bringing the show to different theaters and improv festivals.

In honor of our three-year anniversary, I wanted to share my top 5 favorite moments over the last three years. They are in no particular order, but they are the things that have had a lasting impact on me. What has been your favorite moment from the show so far? Let us know in the comments.

  1. Interviewing George Wendt
    As a fat, insecure 19-year-old kid from the suburbs, I would drive my parents Buick station wagon into the city of Chicago to take improv classes at The Players Workshop of The Second City. On the wall was grainy head shot of a young George Wendt. At the time, Cheers was on NBC and was quickly becoming must see TV. I related to the lovable loser of Norm Peterson and to the actor who played him, George Wendt, who started out at The Player Workshop before making it to Main Stage at Second City.I wanted to be a character like Norm on a sitcom like Cheers and have a career like George’s. He was an inspiration, something I aspired to be. When he agreed to be on Improv Nerd Live in Chicago more than 30 years later, over Facebook, I was so excited and scared. The show was incredible. Apparently I wasn’t the only one who loved George Wendt, because the place was packed. That night, it seemed everything had come full circle. Listen >
  1. Meeting Key and Peele
    It’s always cool to get a guest right when they are about to blow up. We interviewed Key and Peele in a conference room at Second City. Everyone in the improv community knew how great the show was on Comedy Central and it would be just a matter of time before it would become a huge hit. During our interview, we talked about a lot of things: the show, the critics, adjusting to being in charge, being biracial. It is probably one of the most passionate conversations I have had over the last three years. I remember when I was done, I was exhausted and thought I had offended them, especially Keegan. Months later at the Detroit Improv Festival, Keegan was my guest again, and he assured me everything was OK between the two of us. As someone who suffers from chronic jealousy, I am proud to say that I could not be happier for their success, and having the chance to interview them was a dream come true. Listen >
  1. Getting Picked Up in a Lincoln Town Car
    One of my dreams has been to have my own talk show on TV where I get to interview people in depth, like Charlie Rose. I envision myself living in a big house and being picked up in a Lincoln Town car to be driven to the studio.Although I haven’t scored a TV deal yet out of doing this podcast, I have had experiences where I felt like a big deal. One of the best was when I got to interview Horatio Sanz, who I always thought Horatio was one of the funniest people I knew when I was starting out in Chicago. What made it even sweeter was that the interview was held at my alma mater, Columbia College in Chicago. The day of the interview, Columbia sent a Lincoln Town car over to my house and picked up me and Lauren, and we did the show in packed auditorium. Afterwards there was a reception, and I got my picture taken with the president of the college. I felt like a star. Listen > 
  2. Performing with the Improvised Shakespeare Company
    These guys are great, and I highly recommend anyone to see their show. I was so excited to have Joey Bland and Ross Bryant on as our guests to represent the group, even though I was terrified to improvise in the style of Shakespeare. I had never even read a Shakespeare play before, so a few days before the show, tried reading Shakespeare out loud to my wife, and I had no idea what any of it meant.Before the show, I told Joey and Ross how scared I was, and they said don’t worry. They did not lie. In fact, they really took care of me and it turned out to be a lot of fun. During one of scenes I uttered the phrase “oil of my loins,” where that came from I have no clue, but the audience loved it. And when I heard everyone laughing, I realized I had survived something I thought was going to kill me. Listen > 
  3. Intern enters the scene during the Amanda Blake Davis episode
    This was the strangest thing that I think has ever happened to us. One of our interns, who had Amanda as a teacher at Second City, decided during the improv scene with me and Amanda, that he was going to do a walk on. Which he did. To say I was surprised is understatement. Traumatic is the best way to describe it. I had no idea how to handle it or why it had happened. But afterwards, this event became a learning experience for me, because I realized that I hadn’t really been taking ownership of the show. I had never set ground rules for the interns, and believe it or not, I was supposed to be the leader, even though I had little experience in being one. This episode woke me up out of my sleep and made me realize people were looking to me to lead them. Listen >

Let us know what your favorite moment of the show has been so far!