Rise to Success: Career Highlights of Chris Fleming (comedian)

By Popular Timelines Editorial Team · Updated: March 6, 2026

Discover the career path of Chris Fleming (comedian), from the first major opportunity to industry-changing achievements.

Chris Fleming is an American comedian and actor recognized for their YouTube series Gayle, where they portray the character Gayle Waters-Waters. Their unique comedic style has garnered attention, leading Variety to acknowledge them as one of the '10 Comics to Watch for 2019'. Fleming's work primarily revolves around absurdist and character-based comedy, often utilizing physical humor and distinctive vocal delivery to create memorable and unconventional performances.

Sections (3)

Full Timeline Early Life & Education Career & Achievements

2007: Stand-up performance at HBO's Comedy Festival

In 2007, Chris Fleming performed stand-up comedy at HBO's 13th annual Comedy Festival in Aspen, Colorado.

2010: Move to Los Angeles

In 2010, Chris Fleming moved to Los Angeles after signing with the talent agency who managed Dane Cook, later finding their manager had become a chef.

2011: Description of Fleming's comedy by Rick Jenkins

In 2011, Comedy Studio owner Rick Jenkins described Chris Fleming's comedy as seeing the world in a funny way, filled with over-the-top, self-important characters.

2012: Launch of Gayle series

In 2012, Chris Fleming launched the absurdist comedy series Gayle on YouTube, which was written by Fleming and directed by Melissa Strype.

2013: Margaret Cho guest stars in Gayle episode

In 2013, comedian Margaret Cho guest-starred as Yo-Yo Ma in the Gayle episode "Chibby Point", where Gayle kidnapped Yo-Yo Ma from a Barnes & Noble.

2014: Gayle Live US Tour

In 2014, the Gayle team embarked on a US tour with the show Gayle Live.

2015: "COMPANY IS COMING" video released

In 2015, Chris Fleming released the video "COMPANY IS COMING" starring their Gayle character which went viral.

2015: Final episode of Gayle published

In 2015, the final episode of Chris Fleming's YouTube series, Gayle, was published, marking the end of its 40-episode run.

2016: Release of "Am I A Man?" video

In 2016, Chris Fleming released a video titled "Am I A Man?" lampooning their audience's questions about their gender.

2016: Release of "I'm Afraid to Talk To Men"

In 2016, Chris Fleming satirized their relationship with masculinity in their comedy, such as with their song "I'm Afraid to Talk To Men".

2016: Showpig stand-up comedy tour

In 2016, Chris Fleming toured the United States with their stand-up comedy show Showpig.

2017: Showpig stand-up comedy tour

In 2017, Chris Fleming continued to tour the United States with their stand-up comedy show Showpig.

June 2019: Named one of Variety's "10 Comics to Watch for 2019"

In June 2019, Variety recognized Chris Fleming as one of the "10 Comics to Watch for 2019".

2019: Creation of I'm the Mayor of Bimmi Gardens pilot

Around 2019, Chris Fleming created the WarnerMedia/Adult Swim pilot I'm the Mayor of Bimmi Gardens.

2019: Boba Everyday tour begins

In late 2019, Chris Fleming's stand-up tour Boba Everyday began but was postponed until 2021 due to the COVID-19 pandemic.

October 2020: Announcement of Forest Musings

In October 2020, Chris Fleming announced Forest Musings, a virtual show.

2020: Detailing the experience during Boba Everyday tour

During their 2020 Boba Everyday tour, Chris Fleming described in detail the experience of attending a party at Dane Cook's house in 2012.

2020: Creation of "Sick Jan"

In 2020, Chris Fleming created "Sick Jan", a song and music video detailing their former H&R Block tax preparer's unusual behavior.

August 2021: Announcement of Tricky Tricky tour

In August 2021, Chris Fleming announced their stand-up tour, Tricky Tricky.

2021: Shooting of pilot in Atlanta, Georgia

In the summer of 2021, Chris Fleming's pilot I'm the Mayor of Bimmi Gardens was shot in Atlanta, Georgia, featuring Chris Fleming as the protagonist along with Victoria Pedretti, Perfume Genius, and Ms. Pat.

May 2022: "COMPANY IS COMING" view count

As of May 2022, Chris Fleming's 2015 video "COMPANY IS COMING", starring the Gayle character, had over 13.9 million views.

May 2022: Announcement of summer stand-up tour

In May 2022, Chris Fleming announced a summer stand-up tour with venues in British Columbia, Texas, New York, Ontario, and Vermont.

August 3, 2022: Sharing screenshots of the pilot

On August 3, 2022, Chris Fleming shared screenshots of the pilot for I'm the Mayor of Bimmi Gardens, along with captions explaining scenes and thanking the actors.

2022: Mockumentary-style interview creation

In 2022, Chris Fleming created a mockumentary-style interview with an eccentric character who explains his invention of the word "umpteenth".

2022: Release of "Men and Me" monologue

In 2022, Chris Fleming satirized their relationship with masculinity in their comedy, such as with their monologue "Men and Me."

2024: Full pilot released on YouTube

In late 2024, the full pilot of Chris Fleming's I'm the Mayor of Bimmi Gardens was released on YouTube.

May 2025: YouTube channel subscriber count

As of May 2025, Chris Fleming's YouTube channel has over 465,000 subscribers, featuring a variety of content including Gayle, music videos, and car rants, with additional videos posted on Twitter and Instagram.