Chris Fleming at Cadillac Palace Theatre

Chris Fleming Live Special Taping

Hailing from Massachusetts, the comedy icon began pursuing stand-up comedy in their junior year at The Comedy Studio in Cambridge, marking the start of their passion for the funny business. In 2012, Chris Feming released their acclaimed YouTube series, "Gayle". Starring as the eponymous character Gayle Waters-Waters, the world soon became drawn to their unique, relevant, and specific character comedy. From there on, Fleming's domination caught the global eye.

With a special tour coming up, this is your chance to catch their highly-praised stand-up comedy sets, amusing tales, and relevant social takes alongside their character comedy antics. Known for their progressive and gender-bending role in the funny business, Chris Fleming sure is an unstoppable force today.

The Icon Behind Gayle

The 40-episode YouTube absurdist comedy series is written by yours truly, directed by Melissa Strype who played Gayle's daughter, Terry Gross Waters-Waters. Launched in 2012 and produced through 2015, the online series became a massive hit, cementing their place in the comedy scene. 

Following the story of suburban mom  Gayle Waters-Waters' desire to maintain social status in the fictional Northbread community in Massachusetts, it's a tale inspired by people they've encountered in real life. 

"I did Gayle in my stand-up and she was inspired by a lot of folks that I saw growing up...It kind of cemented as ideas do in a very singular moment when I was in a Crate & Barrel and I saw a woman diving into a barrel of placemats," Fleming shared with WBUR. 

"It's fear of how you're seen in your community, that's what it is, that's the essence of it...Why I related to her so much is just that terror of how others perceive you."

Filmed in their Massachusetts hometown, the comedy series became a community effort - even some neighbors participating as actors on the show. 

By 2025, Fleming's YouTube channel had amassed over 465,000 subscribers, with a variety of content from Gayle, music videos, and social rants. In 2015, their video "COMPANY IS COMMING" became crazy viral with millions of views. Known for their unique character comedy, the icon creates various personas inspired by people around them, such as "Sick Jan" and "DePiglio" which are their personal favorites. 

When it comes to stand-up comedy, he's been described by Comedy Studio owner Rick Jenkins as - "Chris isn't a funny comedian; he's an interesting person who sees the world in a funny way." The comic is able to share a world that's become a "cartoonish, absurd place filled with over-the-top, self-important characters."

Performing stand-up shows this year, Chris Fleming is all set to take you on a wild ride through amusing characters in an absurd world. Get ready to laugh your socks off, so book those tickets now!