Hip To Be Square Comedy Bringing Big Names to Knoxville Comedy Scene

Square Room, Off Market Square
Gary Jackson, Hip to Be Square (Photo by Heather Ryerson)

(Ed. Note: Today’s article is by guest writer Heather Ryerson)

Knoxville is quickly making a name for itself as a music city. We have a large and beautiful maker and artist community. Film fests are making their way into our theaters. One man feels it is time to bring the comedy scene to the forefront and he’s doing it on Market Square at the Square Room.

Gary Jackson, an Alabama native, has a degree in computer information systems. He has worked in internet development, data science, and other things that I cannot pretend to understand. His LinkedIn page will make your head swim with all his accomplishments. His day job in data science has allowed him to travel worldwide and encounter a wide range of people and cultures. He is still working in the world of tech and AI. You can hear more about his work in this field on March 26th at the TEDxUTK Conference with other local professionals to discuss the world of technology. 

Back to comedy. What began as a challenge to an open mic night after work in Pakistan (Yep. He has even worked with the CIA.) has become a passion for him. While comedy may not seem the natural side hustle for a data scientist, once Gary was bitten by the comedy bug, he couldn’t let it go. You can hear more about what he believes is the connection between comedy and data science in a YouTube video here.

Gary’s story is fascinating, and we didn’t have enough time to cover even half of the stories he has to tell! For example, his boss asked him to go to Hong Kong to accompany him on a job. He said yes, as I’m discovering he does a lot! For the cliff’s notes on his comedy background, read more here. After moving to Hong Kong, he promptly searched out Jami Gong of Take Out Comedy, the first full-time comedy club in Asia. Jami grew up in NY and, after visiting Hong Kong upon his grandmother’s passing, moved to take comedy to Asia.

Jami mentored Gary in his comedy trade, and Gary, among others, contributed to the rising comedy scene in Asia from 2009-2016. He was even part of a documentary produced by Apple TV called I Need You to Kill, based on the rise of comedy there. Gary has worked with recognizable names like Paul Ogata, Tom Cotter, Trevor Noah, Ronny Chieng, Roy Wood Jr., Russell Peters, Tony Baker, Tom Segura, and many, many more. He has performed stand up across the U.S. , as well as all over the world, including gigs in London, Cape Town, Johannesburg, São Paulo, Tokyo, Manila, Perth, Sydney, Melbourne, Jakarta, Singapore, Kuala Lumpur, to name a few.

Square Room, Off Market Square (Photo courtesy of Gary Jackson)

He also opened comedy clubs in the Philippines and Colorado Springs. He now brings his talents and connections to Knoxville as the founder of Hip To Be Square Comedy @ the Square Room! Gary has worked with Comedy Central, Spaces in the City, and Downtown Knoxville Courtyard Marriott/Residence Inn to make this move happen.

Before moving to Knoxville, Gary was firmly planted in Asheville, NC, with no plans to leave. Through a dating app glitch that told him he and his latest match were in the same town, Gary drove the 2 hours from Asheville to Knoxville to have dinner with a girl. Knoxville and Brenda worked their magic and he moved to our fair city and married the girl.

Gary has a heart for paying it forward to local comics and feels a need for mentoring, connecting, and training a new generation of comics in the city. To do this, he wants to bring in seasoned and well-known comedians who can bring the attention to comedy that it deserves and allow local acts to hone their craft and help them connect with a bigger audience. In the first show, featuring well-known comic Paul Ogata, he will have local openers  Beth Tomkins, founder of True Grit Comedy, Madison Duren, and the host himself, Gary Stephen Jackson.

Gary believes comedy doesn’t have to be raunchy to be funny. His goal is to connect with the heart of the crowd through personal stories and levity. He believes that people all want the same few things. We want to fall in love, know that we are not alone and belong somewhere, and everyone is seeking a reason to laugh.

As an optimist and cheerleader for all the good in the world, I must agree. The more of Knoxville I experience, meeting people, learning about businesses through this incredible platform, the more I believe Knoxville has something unique. We have a thriving community of people who want to support each other and bring a smile to the community around them. From buskers in Market Square to KISS caboose drivers, from food artists to dream jewelry makers, we all have a chance to be the reason someone smiles today.

March 24-25th is Gary’s turn to make Knoxville smile!

Shows at The Square Room will be one weekend a month, March through August (You’re welcome, sports fans!) in 2023. There will be 4 shows each weekend: two on Friday nights and two on Saturday nights, 7:00 pm and 9:30 pm. The 7 pm shows will be rated PG-13, and the 9:30 shows will be rated PG-13 to R. 

Here’s the lineup for 2023:

PAUL OGATA (Comedy Central, The Late Late Show, Showtime, Amazon, and Celebrity Family Feud) March 24, 25

CAMILLE SOLARI (Comedy Central, Arsenio, Oxygen, Amazon, and TMZ) April 28, 29

MYQ KAPLAN (Comedy Central, Last Comic Standing, Late Night with Seth Meyers, Late Show with David Letterman, The Late Late Show, Conan, The Tonight Show with Jimmy Fallon) May 19,20

TIM YOUNG (E! Last Comic Standing, MTV, and TLC) June 30, July 1

DWAYNE PERKINS (Comedy Central, Netflix, Conan, Amazon, The Late Late Show, Jay Leno) July 28, 29

CAITLIN PELUFFO (The Late Late Show with James Corden, Late Show with Stephen Colbert) August 18, 19

  • Tickets at the door are $35
  • Preshow online tickets are $30
  • Group discount – $100 (4 persons)
  • UT Knoxville, ETSU, Pellissippi Student, Military discounts (with valid student and military ids) – $20 

Buy tickets here. Keep up with the latest news on their website, Instagram, Facebook, and Twitter. Still need more? Contact Gary at 1-865-333-4577 or hiptobesquarecomedy@gmail.com.