[14] The series is written by Fleming and directed by comedian Melissa Strype, who also plays Gayle's daughter, Terry Gross Waters-Waters.

The series follows high-strung, eccentric suburban mother Gayle Waters-Waters and her ruthless journey to uphold social status in the small, fictional community of Northbread, Massachusetts.

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.

In 2013, she guest starred in the episode "Chibby Point" as Yo-Yo Ma, whom Gayle kidnapped from a Barnes & Noble.

Although much of his hometown supports the series, with some neighbors even participating as actors,[13] Fleming claims:There's one woman, who a lot of [Gayle] was inspired by, who is NOT happy about it, at all...[she's] absolutely pissed [because her full name is used for a background character].

[16] Fleming has expressed regret that COMPANY IS COMING, a viral 2015 short featuring Gayle,[22][23][24][25] is the series' best known project and "what I get stopped at airports for.

In addition to Gayle, Fleming has a variety of other content that ranges from music videos to car rants.

His 2015 video "COMPANY IS COMING,"[23] starring his Gayle character, went viral, accruing over 13.9 million views as of May 2022.

You promised me your soul for your video COMPANY IS COMING going viral, and now sorority girls from the South like you for all the wrong reasons!

In 2020, he created "Sick Jan," a song and music video detailing his former H&R Block tax preparer who exhibited unusual behavior that intrigued Fleming.

... [The] story 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.

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

[32] Upon arriving, Fleming realized he was at comedian Dane Cook's house, and it was a watch party of the NFL playoff between the Patriots and the Ravens.

[31][33] While receiving a tour of the house, Fleming complimented its appearance, comparing it to a Crate & Barrel; Cook was not amused by the joke.

[31] Dressed in androgynous clothing and having no knowledge about football, Fleming felt "freak[ed] out" and claims to have lost his sense of spatial awareness.

[31] Fleming lampoons their differences in appearance by displaying the Bostonian comedians with a Dropkick Murphys song; then his own face accompanied by "Last Christmas" by Wham!

"[37][38] Fleming's stand-up tour entitled Boba Everyday began in late 2019 and was postponed until 2021 due to the COVID-19 pandemic.

[41] In May 2022, he announced a summer stand-up tour with venues in British Columbia, Texas, New York, Ontario, and Vermont.

In 2016, Fleming gave the following definition for manhood:My concept of a man is someone who whacks their elbow a little bit at a Bertucci's and has no hang-ups about freaking out—zero qualms about going full Streetcar Named Desire at 2 PM...[45]Fleming satirizes his relationship with masculinity in his comedy, such as with his 2016 song "I'm Afraid to Talk To Men"[46] and 2022 monologue "Men and Me.

In regards to his appearance, he has compared himself to "a cocker-spaniel who is bi at best,"[45] a "woman [...] from the woods"[31] and "an American Girl doll that got left out in the rain.