History of Chris Fleming (comedian) in Timeline

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.

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Full Timeline Early Life & Education Career & Achievements

January 29, 1987: Chris Fleming is born

On January 29, 1987, Chris Fleming, an American comedian and actor, was born.

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.

2009: Graduation from Skidmore College

In 2009, Chris Fleming graduated from Skidmore College with a degree in theater and was one credit short of a minor in dance.

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.

January 2012: Meeting L.A. comedians at Dane Cook's house

In January 2012, Chris Fleming attended a party at Dane Cook's house to meet successful L.A. comedians, feeling out of place due to their androgynous clothing and lack of football knowledge, which led to an embarrassing encounter with Bill Burr.

January 22, 2012: Dane Cook tweets photographic lineup of comedians at the party

On January 22, 2012, Dane Cook tweeted a photographic lineup of comedians at the party, including Chris Fleming.

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: Regret over virality of "COMPANY IS COMING"

In 2015, Chris Fleming expressed regret that the viral short "COMPANY IS COMING", featuring the Gayle character, became the series' best-known project.

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: Definition of manhood

In 2016, Chris Fleming gave a definition of manhood.

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.

2018: Lampoon of viral video as Faustian deal

In 2018, Chris Fleming lampooned their viral video "COMPANY IS COMING" as a Faustian deal with a demon named Davis, highlighting the consequences of viral fame.

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: Character Origin of Gayle

In 2019, Chris Fleming described the origin of the character Gayle, developed through their stand-up comedy, highlighting the character's high-strung and eccentric nature as a suburban mother.

2019: Fleming's comedic process

In 2019, Chris Fleming described their comedic process to WBUR-FM.

2019: Preferred pronouns

In a 2019 interview with The Peak, Chris Fleming stated that "Anything works for me" when asked for their preferred pronouns.

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.

2020: "Sick Jan" and "DePiglio" as personal favorites

In 2020, Chris Fleming stated that "Sick Jan" and "DePiglio" were their personal favorite videos on their YouTube channel.

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: Description of perceived appearance

In 2022, Chris Fleming described how they are perceived by others, comparing themself to "a cocker spaniel who is bi at best", a "woman from the woods", and "an American Girl doll that got left out in the rain", noting their position in the "order of operations" at restaurants.

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."

2022: New York magazine asks about similarities to Deirdre

In 2022, New York magazine asked Chris Fleming about the similarities between "Sick Jan" and Deirdre from the 2022 film Everything Everywhere All at Once.

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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.