Hi! I am Gary Jackson, data scientist, former standup comedian, and founder of HIP TO BE SQUARE COMEDY in Knoxville, Tennessee.

I was part of the Asia comedy scene (Hong Kong, Singapore, Kuala Lumpur, Tokyo, Manila, and Cebu, Philippines) between 2009-2016 that Amazon did a documentary called "I Need You To Kill" starring Tom Segura, Chad Daniels, and Pete Lee.

My home club for nearly a decade was Take Out Comedy Hong Kong founded by Jami Gong. I have performed with Paul Ogata, Tom Cotter, Trevor Noah, Ronny Chieng, Roy Wood Jr., Russell Peters, Tony Baker, Tom Segura, and many, many more.

I was able to perform all over the world including London, Cape Town, Johhannesburg, São Paulo, Tokyo, Manila, Perth, Sydney, Melbourne, Jakarta, Singapore, Kuala Lumpur, Atlanta, Philadelphia, DC, New York City, Nashville, Raleigh, Dallas, and Las Vegas.


I founded a comedy club in Cebu, Philippines in 2015 called "Comedy Cebu", the first point of view comedy club on Lapu Lapu Island (the place where Ferdinand Magellan was killed and some say was eaten).


On March 16, 2016, I was jailed for assaulting an audience member in Hong Kong during a comedy show. I published an article entitled, "The Truth Hurts" about the experience. I was nearly sentenced to five years in maximum security prison but was released after nine weeks.

I nearly gave up standup comedy but in 2017 I moved to Colorado Springs and opened up "Comedy Mayhem At the Mezzaine".


Next I moved to Asheville, North Carolina and focused on data science and blockchain. Prior to OpenAI's ChatGPT, I co-wrote the technology for Esquire Singapore's April 2019 Artificial Intelligence issue that was half written by human and half writen by my startup called I was interviewed by multiple television stations discussing how the technology worked including WLOS in Asheville.

In order to prevent Artificial Intelligence from writing misinformation or creating deep fake videos during the 2020 Presential Election, I co-founded a startup called Blockstamped that uses blockchain to prevent false narratives.


Just before the pandemic, I met my wife and began to commute back and forth between Knoxville, Tennessee and Asheville. As the pandemic grew worse, I fell more madly in love with my wife and the Scruffy City. On October 21, 2021, I married my wife at Capitol Theatre in Maryville, Tennessee.

After getting tired of headliner comedians only playing big venues, I reached out to Spaces In The City and worked on a partnership to start bringing hot, new international standup comedians to the intimate venue called The Square Room.

Our club was created to mix together the best standup comedians from around the world with local Knoxville talent. So bring your friends and your family, and laugh until it hurts.


  •   4 Market Square, Knoxville, TN 37902