29 Jun

Chicago’s Comic: Tucker Brookshire

Tucker Brookshire
Chicago’s Comic
Week of June 29th, 2018

Meet Chicago’s own comedian to watch—Tucker Brookshire.

Q: What inspired you to start stand-up comedy?

A: When I saw Dave Chappelle’s “Killing Them Softly” and Bill Cosby’s “Himself” I was hooked right away. I had always identified as being funny but the fact that you could be paid and appreciated for it seemed too good to be true.

Q: Describe your first performance?

A: I wrote about four minutes of material over the course of two years, moved to Chicago, took that material to an open mic, went dead last out of 45 comics, and then bombed so hard that I did not attempt stand-up for another five months.

Q: Do you have “pre-show” rituals? If so, what are they?

A: I like to do anything besides think about the fact that I’m about to perform. A lot of the time I will do things like list my favorite cereals in my head or have conversations with myself to distract from the fact that I’m probably not funny. I do this until my name is called.

Q: Where in the world is your favorite place to perform stand-up? Why is this your favorite place?

A: The Riff at the Diversey Bowl! I think stand-up comedy is at its best when the performer is being as genuine and authentic as possible. The Riff really pulls that out of the performer. I also like the basement of Brendan’s Pub, its a great lil comedy room.

Q: What shows, podcasts, blogs do you produce or co-produce?

A: Untucked—a bi-weekly web series about fashion and clothing.

Q: What are three of your favorite things?

A: 1.) My Family 2.) Stand Up Comedy 3.) Fashion

Q: What is your favorite sammich?

A: A Turkey Pesto Sandwich.

Q: What’s one thing people assume about you, that is or isn’t true?

A: Yikes. This is the type of question that keeps me up at night. I suppose that a lot of people may see me and think that I’m probably a douchebag or an asshole when in reality I think I’m a very kind and genuine guy. Honestly, people probably don’t assume that as often as I think, I am just very insecure. Either way I like to be on the safe side and assume the worst. Anyways, how about this weather we’re having…

Q: If you weren’t a comic, what other job would you love to do?

A: I would love to be a fashion designer. I’m very into clothes and fashion. My dream is to have my own clothing line, so I real-ly need comedy to work out.

Q: What are some comedy goals/dreams you have on your To Do List?

A: My only real goal is to perform comedy for a living, anything after that is really just a bonus. I would love to become a paid regular at both The Comedy Store and The Comedy Cellar. My biggest dream is sell out my own tour, and to perform on the same show as Dave Chappelle at least once.

Q: What quality, trait and/or body part do you really like about yourself?

A: I hate myself. Deeply. If I have to answer, I guess I’ve learned to love my hair. I am a red head and have been bullied for my hair for most of my life so I feel like we have been through a lot together. One of those—if they hate it, I love it—sort of things.

Q: What’s one thing you wish more people knew about you? [or anything else you’d like mentioned, i.e. your education, personal life or mission statement]

A: How proud I am to be a Brookshire. My family is full of the most morally profound individuals I will ever meet and I am lucky to be surrounded by such an amazing group of people. If I ever do anything significant on this planet I would like to show the world, through my own actions, what it means to be a Brook-shire. I also wish comics would dress better.

Q: How will you know you “Made It?”

A: When I don’t have a day job.


  • 7.13.2018: Bar 63
  • 8.6.2018: “Afterthoughts” – Laugh Factory
  • 8.11.2018: “Apocalypse Comedy” – The Crowd Theater


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