Comedic Dreams in the Windy City with Annie Taylor

April 10, 2015


Annie Taylor found a love of comedy from an early age and since then has made it her mission to share the joy she gets from comedy with others. The driven, ever-humble, Annie on dealing with early loss, turning things around in Chicago, and finding her stride, in this exclusive interview.






I am originally from Danbury, CT. I’m from a very large Irish family and was always putting on shows with my brother and cousins.


My parents nurtured my appreciation for comedy -­‐ they exposed us to things like Harold Ramis, SNL, Billy Crystal & Dave Letterman at a very young age.


I loved making my family laugh and always found a way to perform.


When I was in kindergarten, my teacher put a few of my classmates and me in a band called “The Lion King Band.” My best friend and were the lead singers and we performed during lunches and school picnics. We rehearsed during class and everything… it was very serious.


From there, I created another band, learned how to play violin, was in school plays and musicals, joined choir, competed in poetry slams and eventually found my way into improv.





First Entertainment Job


A few weeks ago, I got my first job coaching an ensemble team at The Second City Training Center. The story behind it isn’t very complicated… Brian Posen asked if I wanted to coach a team and I said yes.


At first, I was really nervous because I’m young and have impostor syndrome, but after my first rehearsal I knew that I was exactly where I’m supposed to be. Teaching isn’t new to me, but I usually teach high school students, who aren’t actively choosing to take my workshops.


Getting to share my love and appreciation of improv with a team of individuals who love this community as much as I do is an incredibly rewarding experience.


I’m grateful that I have the opportunity to return the love and support that I received from my coaches and teachers to my team.


Pete Holmes always says to “humbly and proudly return what you’ve been given” and coaching definitely gives me the ability to do so.





What was it like moving to Chicago from Connecticut?


Thrilling. As much as I love and miss my friends and family, I didn’t really fit in there. Chicago is where I was really able to be the best version of myself.


After my dad died, I had this identity kind of thrust upon me and in Chicago, I could shake it.


It’s not the first thing people think of when they see me. I spent the first four years here without being in the improv community, and they were just as great as the years since.


Major cities attract people who want to get things done… passionate people.


Add the improv community, and I have my home. I’m constantly amazed by all of the love, support and opportunities I’ve been given.


We’re family. It’s the best community there is.





What drew you to improv?


It’s an interesting story. When I was 16, one of my mom’s customers came into her store wearing a leather Saturday Night Live jacket. She chatted with him about how much our family loved Saturday Night Live and how it reminded us of my dad, who died three years earlier.


Turns out that he was Phil Hymes, SNL’s lighting designer. He invited us to the show and gave us the VIP treatment -­‐ we went backstage, met the cast, learned how the show works and had incredible seats.


That night, I learned how powerful comedy was.


Before my SNL experience, I was completely numb with grief. I was the kid with the dead dad who had this massive weight on her shoulders.


However, when I was in Studio 8H, that weight was gone and for three hours, I could just be a teenager.


I vowed that I would dedicate myself to making others feel that way. I became the biggest comedy nerd ever. During the summer, I commuted two hours into New York for improv classes and spent my 17th birthday waiting in line at UCB for ASSSSCAT tickets.


For the first time since my dad’s death, I had something to really live for… an identity.


A few months later, Phil invited me to a Friday afternoon rehearsal. I got to see how the show operated and met my idols, who encouraged me to go to Chicago.


“You’ll find your people there” -­‐ that’s what they kept saying. “Even if you don’t pursue comedy, you’ll find your people there.”


So, I decided to go to DePaul and pursue comedy on the side, however, when I got to college, I stopped improvising. I was only 17, which meant that I was too young to go through iO or Second City.


So I joined a sorority and completely forgot about improv for four years. That was incredibly important. I was able to live life, work through shit and became a whole person again. I even graduated and got a corporate job.


After awhile though, I was sick of answering to people from my hometown. When I left, I was dead set on being a comedian, and I didn’t even try.


I knew that I could live with finding out that I no longer liked improvising, or was no longer good enough, but I couldn’t live with never even trying. So I signed up for my first class in Chicago and fell in love with improv all over again.


I found my people.





You’ve performed improv, written sketches, assistant directed, and now are doing stand-­‐up, in which role(s) do you feel the most comfortable?


It’s hard to compare everything that’s on my resume because I do things for different reasons. Improv and sketch are my passions.


I’ll always feel at home writing, performing, coaching and acting.


They’re things that I love, believe in, and have been doing my entire life. I started assistant directing because I wanted to be part of a process without having to be creative. It allowed me to take a step back and learn how to be a better actor and writer.


I cannot recommend assistant directing a show enough… you learn so much through watching other people work.


Simple things like finding your light or how to carry yourself onstage and bigger things, like how to be a good person to work with. All things that are incredibly important to your success as a performer.


I started stand-­‐up just because I told myself I would never do it… so I did it.







My biggest challenge is convincing myself that I deserve to be here. Throughout my life, I’ve heard “no” more than “yes.”


Whether it was captain of my middle school cheerleading squad, having a role in my high school’s musical or being elected for a second term on my sorority’s executive board, I’ve been told “no” more than “yes.”


So, I can deal with no… I’ve been developing those skills my whole life. It’s harder for me to learn how to deal with success.


In my first 5B class, we had to do a two person scene. When the scene was done, Noah ran diagnostics on us. In my scene, I played an art agent who started listing off all the ways my failing client was impacting my quality of life.


Silly things like “I couldn’t afford another week at the hospital, so I had to pull my dad off life-­‐ support” and “The price of milk went up ten percent so I had to convince my kids that they were lactose intolerant.”


After playing that game for a little, I decided it was time to go on with the scene and resolve my client’s problem.


After the scene was done, Noah goes, “You bailed on your game. Instead of resolving your scene because you think that you have to, listen to what the audience is telling you. You never think you’re good enough, do you?”


After meeting me for the first time, he summed me up as a person. Here’s the truth: most people don’t feel good enough.


We compare our bad days to someone else’s good days without realizing that everyone fails. We beat ourselves up constantly.


Even when faced with success, we convince ourselves that we aren’t deserving, that they got it wrong.


We need to listen to our audience instead. The people who love and support us, the directors who believe in us and give us opportunities.


Yes, persevering through failure is an important skill… but so is learning how to celebrate success.





Use of Social Media


I’m a social media intern at iO, which means that in exchange for classes, I help with their Facebook. This summer, I covered the closing of Clark Street and opening of Kingsbury. I got to catch some really cool shows and felt like part of the community during such an exciting time.


 I also use social media as a digital notebook. When I think of a funny tidbit at work, I throw it up as a status or tweet instead of writing it down.


I don’t have many followers, so it’s not like I do it for likes… but whenever I’m in a writing rut, I’ll scroll through my old posts and I usually catch something funny that inspires me.


It helps keep me sharp and forces me to write constantly.


The other night, I didn’t do my standup homework so I did a whole set off of my old tweets. It killed.


More than anything, it builds a digital community. Comedians are incredibly busy people and it’s hard to find time to catch up or seek advice.


However, with Facebook, you’re always connected.


My teachers post gigs, advice, workshops, articles and countless other resources to help develop my career.


There’s this argument that the digital age is obliterating human interaction, but I disagree. It keeps me connected, sharp and well informed.





Career Ambitions


To keep working hard. It’s funny because there’s so much you can’t control and so many different paths to take. A month after I was cut from my conservatory class, I got a coaching job.


Weeks after I said that I’d never do standup, I did my first set.


All I can do is to keep working hard, stay humble, continue to grow and surround myself with people who support me.


My dream is to create an HBO series. I love the combination of truth based comedy and real life drama.


My favorite shows are ones that I can relate to and see myself in, and that’s very much my voice as both a writer and performer. If I can make you say “Oh. My. God. That’s me!”, then cry, then piss your pants laughing, I’ve done my job.


I’ve also been “writing a book” for like five years. It’d be nice to finish that.





You’re currently training at the iO in level 5b, what are you learning in that level and for those that don’t know, what is level 5b?


5B is the last level of iO’s program, where you come up with an original improv form with your class. After the class ends, you have a seven week run in the DCT where you perform your form.


It’s a lot of fun and you’re able to apply all of the skills you’ve been learning for the past year.


For me, 5B is all about having fun. After training for over a year, this is our last class. I’m such a student -­‐ I’m the person with the notebook and backpack in class, jotting down every word and trying to absorb as much of it as I can.


However, when I went into 5B, I decided to stay in the moment and follow my intuition, trusting that I learned enough throughout the program to carry me through.





Top 5  Moments in Entertainment


1.  My first improv show. I was sixteen and had never even seen an improv show before. I was trained as an actor and writer, so I thought that improv was just a warm-­‐up for acting or a way to generate ideas for sketches. I thought that there was no way an audience would enjoy it… improv didn’t seem like a presentable art form to me.


All I remember from the show was bright lights and lots of laughter. It was the first time I did something that I really didn’t believe would work, and it did!


2. After my first musical, my dad handed me flowers with a note that said “I think this is the beginning of a great new career.” When I got my first paid gig the other week, I immediately thought back to that moment.


 3. iO’s opening. It was a room full of incredible people sharing their passion for improv & chatting about life. It was one of those nights where you feel like, “Oh yeah, I’m were I’m supposed to be in life. This is what the improv community is all about”


4. My first tech as an AD. This is how crazy the day was: work 6am-­‐5:45pm, class 7-­‐10pm, tech 10pm-­‐5am, back to work from 6am-­‐5:45pm, and rehearsal from 7pm-­‐10pm. It was my 40-­‐hour marathon that proved that I was able to withstand the craziness of theater without turning into a negative or whiny person. I was really proud of how I carried myself and remained positive throughout that day. I look to it as the night that I realized I could really do this.


5. My most recent birthday party. I’m a huge believer of a cohesive Chicago comedy community that includes all theaters. I was elated during my birthday party this year because the back bar of Corcoran’s was Pilled with people from iO, Second City, Annoyance, ComedySportz, pH and friends aren’t in the improv community… all having fun and enjoying time together.


I had this moment where I stepped back and was just like, this… this is what it’s about.





You’re new to stand-­‐up, how are you enjoying it?


It’s fun, it’s a great way to test out my monologue jokes for sketch packets. Sometimes, I get too into my head because I’m definitely a clean comic.


I appreciate all types of comedy, but I’m just not interested in making dick jokes.


Which means that I have to work really hard to make people laugh, especially as a female comic. I never really felt underrepresented in the improv or sketch world, but I constantly do in the standup world.


It just motivates me to work harder and prove everyone wrong. I can be a funny chick who doesn’t make dick jokes.





Tell us about your comedy festival experience. In what ways has that been beneficial to your comedic development?


Performing in festivals is a lot of fun, and most times it’s just that. Fun. Coming together in a space where we can share our common love for comedy and celebrate each other. I don’t know why so many performers put such pressure on themselves during festivals.


Just go out there, have fun, and enjoy this moment. I guess that goes for all shows.


We performed at this festival, OstrichFest, in the middle of nowhere Wisconsin last summer and I learned so much about improvising through that experience. We watched a couple groups go up and try intricate long form pieces and the audience simply didn’t get it.


So, we decided to do short form, and it killed. Chicago is saturated with improvisers performing for improvisers, so we often forget what is appealing to the general public.





Career Preparation


When I was younger, I was in musicals, plays, choir and took violin, voice and acting classes. As a teenager, I did the improv boot camp at Second City in NYC, then developed my own weeklong workshop and taught it at my high school.


In Chicago, I’ve trained at iO, Second City and was in the genesis league at ComedySportz.







 Everything I am is because of those who contributed to my development as an improviser, writer, director, and human.


The amount of time, care and love that Jay Sukow invests in me is astounding. He’s family to me and I can only hope to live up to his legacy as a teacher and mentor.


He taught me to surround myself with people that I love and trust, and encourages me to follow whatever it is that scares me. Most of my eye for directing comes from him, as I spent countless hours assistant directing his shows and watching shows around Chicago with him then discussing what worked, what didn’t, and how we’d change it.


Along with Sukow, my love and appreciation for comedy is thanks to the endless lessons and support from Craig Uhlir, Dana Quercioli, Adal Rifai, Katie Rich, Jay Steigmann, and Brian Posen.


Also, my family. They’re who taught me how important it is to make others happy, which is the foundation of comedy.





Current Projects


I’m currently assistant directing a show called Let’s Not Fight, which is at pH on Sundays at 7:30 until April 26th.


I have 5B shows at 7pm starting at the end of April in the DCT, and am coaching an improv team that has shows at 10:30pm on Thursdays in Donny’s Skybox from April 30-­‐May 21st.





Anything else you’d like to share with our readers?


Don’t get bitter and enjoy every second of this journey without rushing to get to any sort of destination.


There’s this trend among improvisers to have to do everything so that someone will notice them and say, “Hey! You’re doing that!” We rush from show to show to show because we’re on six different teams and we all start to look exactly the same.


When you feel like you need to do something, you lose the joy and passion that is so important to carry onstage with you.


Check in with yourself and make sure that you’re still enjoying every moment.


Take it one show at a time so that you can contribute all of your energy and talent to your team. Also, be professional in everything you do.


Don’t be late, don’t have an ego, don’t act like you know everything. We don’t. We’re young, and the best people I know still consider themselves students.


Always look for an opportunity to learn. A bad show, a job you didn’t book, a team that falls apart… they’re all learning moments.


Be a good person. I only want to work with good people who are interested in having fun and creating something collectively.


Also, learn something new. Have a role in a show that isn’t performing or writing. Take a step back and remind yourself of how cool it is to just be here.





Where can people go to find out more information about you and your work?


Follow me on Instagram and Twitter: @annierosetaylor


My blog -  Controlled Chaos




Thank you for reading! If you enjoyed this interview, please share it.


Help us continue to provide quality interviews & content by following us on Facebook:





Contact us Today at - to become the exclusive sponsor of this interview.










Please reload

Featured Posts

Chelsey Crisp, on Acting, Roles on ABC's "Fresh Off the Boat," Latest film "InLawfully Yours," & Work with the Improv Group -...

May 10, 2016

Please reload

Recent Posts
Please reload

Never Miss An Update

  • Black Facebook Icon
  • Black Instagram Icon
  • Black Twitter Icon
  • Black Pinterest Icon