Chris Fleming (born January 29, 1987) is an American comedian and actor best known for his
YouTube
YouTube is a global online video sharing and social media platform headquartered in San Bruno, California. It was launched on February 14, 2005, by Steve Chen, Chad Hurley, and Jawed Karim. It is owned by Google, and is the second most ...
series ''Gayle'', in which he stars as the eponymous character Gayle Waters-Waters. In June 2019, ''
Variety
Variety may refer to:
Arts and entertainment Entertainment formats
* Variety (radio)
* Variety show, in theater and television
Films
* ''Variety'' (1925 film), a German silent film directed by Ewald Andre Dupont
* ''Variety'' (1935 film), ...
'' named Fleming one of its "10 Comics to Watch for 2019".
Fleming is known for his unique, specific
character comedy
Character comedy is a genre in which a comedian performs as a character they have created.
List of character comedians
Notable character comedians include:
*Tim Allen – Plays a handyman in ''Home Improvement'' and his stand-up routines
*Rowan ...
and "powerful, ridiculous songs." Much of Fleming's comedy is aimed at deconstructing social norms, including masculinity.
He has been described as accruing an online
cult following
A cult following refers to a group of fans who are highly dedicated to some person, idea, object, movement, or work, often an artist, in particular a performing artist, or an artwork in some medium. The lattermost is often called a cult classic ...
.
A staff writer for
FSUNews covering an appearance at
Florida State University praised his stand-up's underlying message, stating, "Fleming does not seem to give too much respect to anything, including himself, which allows him to rid different social norms and constructs of their power."
Fleming has been described as a "progressive gender-bending role model."
Fleming has stated that xie accepts any pronouns, stating, "Anything works for me."
Early life and education
Fleming grew up in
Stow, Massachusetts
Stow is a town in Middlesex County, Massachusetts, United States. The town is located west of Boston, in the MetroWest region of Massachusetts. The population was 7,174 at the 2020 United States Census. Stow was officially incorporated in 1683 ...
and attended
Nashoba Regional High School. During his junior year, he began stand-up comedy at The Comedy Studio in
Cambridge, Massachusetts
Cambridge ( ) is a city in Middlesex County, Massachusetts, United States. As part of the Greater Boston, Boston metropolitan area, the cities population of the 2020 United States Census, 2020 U.S. census was 118,403, making it the fourth most ...
, studying under Rick Jenkins.
In 2007, Fleming performed stand-up during
HBO
Home Box Office (HBO) is an American premium television network, which is the flagship property of namesake parent subsidiary Home Box Office, Inc., itself a unit owned by Warner Bros. Discovery. The overall Home Box Office business unit is ba ...
's 13th annual
Comedy Festival
A comedy festival is a celebration of comedy with many shows, venues, comedy performers (such as stand up comics, sketch troupes, variety performers, etc.) and is held over a specific block of time. Normally, each festival has a diverse range of c ...
in
Aspen, Colorado
Aspen is a home rule municipality that is the county seat and the most populous municipality of Pitkin County, Colorado, United States. The city population was 7,004 at the 2020 United States Census. Aspen is in a remote area of the Rocky Mo ...
.
He received a degree in theater from
Skidmore College
Skidmore College is a private liberal arts college in Saratoga Springs, New York. Approximately 2,650 students are enrolled at Skidmore pursuing a Bachelor of Arts or Bachelor of Science degree in one of more than 60 areas of study.
History
S ...
in 2009,
and graduated one credit short of receiving a minor in dance.
''Gayle''
''Gayle'' is a 40-episode, absurdist comedy series on YouTube.
The series is written by Fleming and directed by comedian Melissa Strype, who also plays Gayle's daughter, Terry Gross Waters-Waters.
It was launched in 2012 and its final episode was published in 2015.
The series follows high-strung, eccentric suburban mother Gayle Waters-Waters and her ruthless journey to uphold social status in the small community of Northbread,
. Fleming developed the idea for ''Gayle'' through his stand-up comedy.
In 2019, Fleming described the origin of her character:
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
Euromarket Designs Inc., doing business as Crate & Barrel (stylized as Crate&Barrel), is an international furniture and home décor retail store headquartered in Northbrook, Illinois. They employ 8200 employees across over 100 stores in the Uni ...
and I saw a woman diving into a barrel of placemats. Like her legs were up in the air, and she was just digging through these placemats...it just kind of came from there...I just plucked her from a tree...I have elements of her in my psyche too; it's not gender-specific thing. 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.
Fleming's mother co-stars as Bonnie, Gayle's best friend and biggest rival (i.e.,
frenemy
"Frenemy" (also spelled "frienemy") is an oxymoron and a portmanteau of " friend" and "enemy" that refers to "a person with whom one is friendly, despite a fundamental dislike or rivalry" or "a person who combines the characteristics of a friend ...
).
Gayle's sensitive
birdwatching
Birdwatching, or birding, is the observing of birds, either as a recreational activity or as a form of citizen science. A birdwatcher may observe by using their naked eye, by using a visual enhancement device like binoculars or a telescope, b ...
husband, Dave, does not reveal his face during ''Gayle''; his voice is provided by Fleming, while his legs are portrayed by Fleming's father.
The soundtrack was composed by Brian Heveron-Smith,
Tom Lowery, and Chris Hartford. The series is filmed in Fleming's hometown in Massachusetts.
''
Forbes
''Forbes'' () is an American business magazine owned by Integrated Whale Media Investments and the Forbes family. Published eight times a year, it features articles on finance, industry, investing, and marketing topics. ''Forbes'' also r ...
'' reported that, in the off-seasons of filming ''Gayle'', Fleming worked as an
SAT
The SAT ( ) is a standardized test widely used for college admissions in the United States. Since its debut in 1926, its name and scoring have changed several times; originally called the Scholastic Aptitude Test, it was later called the Schol ...
tutor.
Circa 2013, comedian
Margaret Cho
Margaret Moran Cho (born December 5, 1968) is an American comedian, actress, LGBT social activist, and musician. She is known for her stand-up routines, through which she critiques social and political problems, especially regarding race and se ...
grew an interest in the show. In 2013, she guest starred in the episode "Chibby Point" as
Yo-Yo Ma
Yo-Yo Ma ('' Chinese'': 馬友友 ''Ma Yo Yo''; born October 7, 1955) is an American cellist. Born in Paris to Chinese parents and educated in New York City, he was a child prodigy, performing from the age of four and a half. He graduated from ...
, whom Gayle kidnapped from a
Barnes & Noble.
In 2014, the ''Gayle'' team went on a US tour with the show titled ''Gayle Live''.
Although much of his hometown supports the series - with some neighbors even participating as actors
- Fleming claims:
There's one woman, who a lot of aylewas inspired by, who is NOT happy about it, at all... he'sabsolutely pissed ecause her full name is used for a background character I forget to change people's names sometimes, so a lot of my life has been trying to explain to people's faces that something that is very obviously about them is not about them.
Fleming has expressed regret that COMPANY IS COMING, a viral 2015 short featuring Gayle,
is the series' best known project and "what I get stopped at airports for."
He dislikes when Gayle is known purely as a "crazy mom character," claiming her character transcends the stereotype:
I've played that character for so long I have such love for her...there's so many different facets to her. That's just one part of her being. I hate that that's what people think of her in general. There's so many other beautiful shades to her psyche.
Sketch comedy
Fleming runs a YouTube channel under his full name; the channel has gained over 436,000 subscribers as of May 2022. In addition to ''Gayle'', Fleming has a variety of other content that ranges from music videos to car rants. He also posts videos on his Twitter and Instagram pages.
His 2015 video "COMPANY IS COMING,"
starring his Gayle character, went viral, accruing over 13.9 million views as of May 2022. In 2018, Fleming has lampooned this viral video as a
Faustian bargain
Faust is the protagonist of a classic German legend based on the historical Johann Georg Faust ( 1480–1540).
The erudite Faust is highly successful yet dissatisfied with his life, which leads him to make a pact with the Devil at a crossroa ...
with a demon named Davis, who says, "We made a deal; one viral video in 2015 for a lifetime of servitude! You promised me your soul for your video COMPANY IS COMING going viral, and now sorority girls from the
South
South is one of the cardinal directions or compass points. The direction is the opposite of north and is perpendicular to both east and west.
Etymology
The word ''south'' comes from Old English ''sūþ'', from earlier Proto-Germanic ''*sunþa ...
like you for all the wrong reasons!"
Fleming is known for his specific, unique
character comedy
Character comedy is a genre in which a comedian performs as a character they have created.
List of character comedians
Notable character comedians include:
*Tim Allen – Plays a handyman in ''Home Improvement'' and his stand-up routines
*Rowan ...
.
In 2020, he created "Sick Jan," a song and music video detailing his former
H&R Block
H&R Block, Inc., or H&R Block, is an American tax preparation company operating in Canada, the United States, and Australia. The company was founded in 1955 by brothers Henry W. Bloch and Richard Bloch.
As of 2018, H&R Block operates approxima ...
tax preparer who exhibited unusual behavior that intrigued Fleming.
In 2022,
''New York'' magazine interviewed him based on Sick Jan's similarities to Deirdre, a character in 2022 film
''Everything Everywhere All At Once''. Fleming stated,
Jan's not an archetype, Jan's such a specific woman. ... hestory of Sick Jan, the character herself, is so dense — maybe it's just that all tax preparers have a vibe of anarchy and Southwestern style. With Jan, obviously, it was one song, so I could focus only on the fact that she was chronically sick for three years and never addressed it. And also her desire to go to jail — her overwhelming desire. People talk about sexual tension in the video a lot, but it's just between Jan and the prison system. ... I remember putting her on speakerphone so my friends could hear her, because she would use this catchphrase while also coughing.
In 2020, Fleming stated that "Sick Jan" and "DePiglio" are his personal favorite of his YouTube videos.
In 2022, Fleming created a
mockumentary
A mockumentary (a blend of ''mock'' and ''documentary''), fake documentary or docu-comedy is a type of film or television show depicting fictional events but presented as a documentary.
These productions are often used to analyze or comment on ...
-style interview with an eccentric male character who explains his invention of the word "
umpteenth."
Stand-up comedy
In 2010, the 24-year-old Fleming moved to Los Angeles after signing with the talent agency who managed
Dane Cook
Dane Jeffrey Cook (born March 18, 1972) is an American stand-up comedian and film actor. He has released six comedy albums: '' Harmful If Swallowed''; ''Retaliation''; ''Vicious Circle''; '' Rough Around the Edges: Live from Madison Square Garde ...
.
Fleming has stated, "I was signed to a manager who seduced me to moving out to L.A., and as soon as I got there, she promptly became a chef."
In 2011, describing Fleming's brand of comedy, Jenkins stated, "Chris isn't a funny comedian; he's an interesting person who sees the world in a funny way. Chris's world is this rubbery, cartoonish, absurd place filled with over-the-top, self-important characters. It's a really cool world he shows us."

In January 2012, Fleming's friend, comedian
Gary Gulman
Gary Lewis Gulman (born July 17, 1970) is an American stand-up comedian. He was a finalist on the NBC reality-talent show ''Last Comic Standing'' in its second and third seasons. He released his first CD, '' Conversations With Inanimate Objects'' ...
, invited to Fleming to a party to meet successful L.A. comedians from Boston. Upon arriving, Fleming realized he was at comedian
Dane Cook
Dane Jeffrey Cook (born March 18, 1972) is an American stand-up comedian and film actor. He has released six comedy albums: '' Harmful If Swallowed''; ''Retaliation''; ''Vicious Circle''; '' Rough Around the Edges: Live from Madison Square Garde ...
's house, and it was a watch party of
the NFL playoff between the
Patriots and the
Ravens
Ravens may refer to:
* Raven, a species of the genus ''Corvus''
Sports
* Anderson Ravens, the intercollegiate athletic program of Anderson University in Indiana
* Baltimore Ravens, a professional American football franchise
* Benedictine Ravens, ...
.
While receiving a tour of the house, Fleming complimented its appearance, comparing it to a
Crate & Barrel
Euromarket Designs Inc., doing business as Crate & Barrel (stylized as Crate&Barrel), is an international furniture and home décor retail store headquartered in Northbrook, Illinois. They employ 8200 employees across over 100 stores in the Uni ...
; Cook was not amused by the joke.
Dressed in androgynous clothing and having no knowledge about football, Fleming felt "freak
dout" and claims to have lost his sense of
spatial awareness
Spatial contextual awareness consociates contextual information such as an individual's or sensor's location, activity, the time of day, and proximity to other people or objects and devices.Chen, Guanling, and David Kotz. 2000. A Survey of Context- ...
. He sat on
Bill Burr
William Frederick Burr (born June 10, 1968) is an American stand-up comedian, actor, filmmaker, and podcaster. He has released multiple stand-up comedy specials, most notably ''Why Do I Do This?'' (2008), ''Let It Go'' (2010), ''You People Are A ...
's armrest "like a
toy breed," eventually humiliating himself by sneezing "directly into the pleat of Bill Burr's khakis." During his 2020 ''Boba Everyday'' tour, Fleming describes the experience in detail.
On January 22, 2012, Dane Cook tweeted a photographic lineup of comedians at the party, including Fleming. Fleming displayed this photo at the end of the stand-up routine as photographic evidence of the described party.
Fleming lampoons their differences in appearance by displaying the Bostonian comedians with a
Dropkick Murphys
Dropkick Murphys are an American Celtic punk band formed in Quincy, Massachusetts in 1996. Singer and bassist Ken Casey has been the band's only constant member. Other current members include drummer Matt Kelly (1997– ), singer Al Barr (1 ...
song; then his own face accompanied by "
Last Christmas
"Last Christmas" is a song by British pop duo Wham!, originally released in December 1984 on CBS Records internationally and as a double A-side on Epic Records with "Everything She Wants" in the UK. Described as a "high watermark of mid-80s ...
" by
Wham!
Wham! (briefly known in the US as Wham! U.K.) were an English pop duo formed in Bushey in 1981. The duo consisted of George Michael and Andrew Ridgeley. They became one of the most commercially successful pop acts of the 1980s, selling more ...
In 2016 and 2017 he toured the United States with his stand-up comedy show titled ''Showpig''. When asked the meaning of the title, Fleming stated, "I fancy myself a
showpig – grease me up and send me to market!"
Describing his comedic process to
WBUR
WBUR-FM (90.9 FM) is a public radio station located in Boston, Massachusetts, owned by Boston University. It is the largest of three NPR member stations in Boston, along with WGBH and WUMB-FM and produces several nationally distributed prog ...
in 2019, Fleming said,
I burn the formula every time I make something. I really revel in making things that no one is asking for. I think it might be the nature of being anti-establishment
An anti-establishment view or belief is one which stands in opposition to the conventional social, political, and economic principles of a society. The term was first used in the modern sense in 1958, by the British magazine '' New Statesman' ...
is like, when people like something they're like "Oh we want more of this," I'm going to give them something completely out of left-field. I think that's a way to make inspired work. To follow yourself and not to follow what David Bowie called "The Gallery."
Fleming is likely referring to Bowie's advice for young artists, in which Bowie says, "Never play for the gallery...Never work for other people at what you do."
Fleming's stand-up tour entitled ''Boba Everyday'' began in late 2019 and was postponed until 2021 due to the COVID-19 pandemic. In October 2020, Fleming announced ''Forest Musings'', a virtual show. In August 2021, Fleming announced his stand-up tour, ''Tricky Tricky''. In May 2022, he announced a summer stand-up tour with venues in British Columbia, Texas, New York, Ontario, and Vermont.
When
''Vulture'' asked for the best comedy advice he had received, Fleming responded, "Rick Jenkins, owner of the Comedy Studio
n Harvard Square">Harvard_Square.html" ;"title="n Harvard Square">n Harvard Square taught me that, through clarity with your audience, even the most absurd idea can be accessible - also, that no idea is too absurd."
Gender identity
Fleming lampooned his audience's questions about his gender in a 2016 video titled "Am I A Man?" His response was, "Can I consider myself a man if, in a pinch, I can dry myself off with a hand towel?"
When asked for his
preferred pronouns
Preferred gender pronouns or personal gender pronouns (often abbreviated as PGP) are the set of pronouns (in English, third-person pronouns) that an individual wants others to use in order to reflect that person's gender identity. In English, ...
in a 2019 ''The Peak (newspaper)">The Peak'' interview, Fleming stated, "Anything works for me."
in his comedy, such as with his 2016 song "I'm Afraid to Talk To Men" and 2022 monologue "Men and Me."
Fleming routinely describes the way he is perceived by others in his stand-up. In regards to his appearance, he has compared himself to "a cocker-spaniel who is bi at best,"
In 2022, he stated, "If I'm at a restaurant with a group, the waiter will ask the women, me, children, then men. That's the order of operations...I've got a
in the summer of 2021.
It featured Fleming as the protagonist, a "mayor of a town off the coast of Florida (but technically a territory of Maine)."
.
didn't get picked up by the network that we made it for, so we're trying to get it somewhere else."
On August 3, 2022, Fleming shared screenshots of the pilot along with captions explaining scenes and thanking the actors.