I’m Comedian Chris Fleming, And This Is How I Work

I’m Comedian Chris Fleming, And This Is How I Work

Chris Fleming first became famous as Gayle Waters-Waters, the high-strung mum on Fleming’s YouTube show Gayle. Since then he’s branched out with music videos such as I’m Afraid to Talk to Men and monologues such as Teens Who Drink Coffee, and he recently wrapped up a cross-country US live tour. We asked him about his evolving comedy career, and he answered us, and he was funny.

Photo by Alexandra Genova

Location: Los Angeles

Current Gig: Comedian/Video Producer

One word that best describes how you work: Frantic

Current mobile device: iPhone 7, shattered screen

Current computer: MacBook Pro

First of all, tell us a little about your background and how you got to where you are today.

I started doing stand up and character-based comedy as a teen. I used to take a bus from Boston to New York City to do two minutes at a comedy club for well-dressed, cruel divorcees. A lot of guys wearing blazers and jeans – the universal uniform of somebody trying but failing to have an affair. Now I make online videos and tour a live show called Showpig.

Take us through a recent workday.

Had a call about a live taping I’m doing this month, freaked out, drove to vegan doughnut shop, ate doughnut in my car, walked my bichon. Edited a music video I directed for a folk band that’s not due ’til next month and avoided something crucial I need to have done by tomorrow. Then I sat down and tried to figure out why every time I’m in my backyard for the last two months a crow has dropped something at my feet, be it a half-eaten avocado or peanut shell, then I researched crows and found they remember human faces and give gifts to those who are kind to them. That’s strange, I don’t remember being particularly nice to any crow recently. Then I have a flash memory of my neighbour, who is identical to me, and I mean IDENTICAL, feeding crows in his front yard. Jesus Christ… I’ve been cashing in on this guy’s good crow ju-ju for months.

But in my defence it’s not like they’re giving me anything good – it’s not like shit from Sephora. It’s like when you’re young and your uncle gives you a map of St Louis.

Then I took a bath.

What apps, gadgets or tools can’t you live without?

Whenever I’m in a conversation I don’t wanna be in I say “one second” and go on my phone, like I’m texting or taking care of business, but really what I’m doing is basic equations on my iPhone calculator. Like seven minus one plus two equals… 8, OK. Then I rejoin the conversation. Also I have an app called AllPaws where I track Neapolitan Mastiffs in my area.

What’s your workspace setup like?

I rent office space in Madame Tussaud’s Wax Museum so it’s too loud to get anything done for the most part. Nah: I have a home office with a bunch of masks on the wall, and my office assistant is my bichon who I spend most of my day staring at.

What’s your best time-saving shortcut or life hack?

Who am I to be answering these questions about workflow – the creator of Thinx underwear? Only shortcut I can think of is getting so obsessively into something that I don’t realise I’ve been spending 14 hours on it and not eaten. Honestly feels really good. I read somewhere or dreamt that this happened to Beyoncé on the set of that Austin Powers movie but for 48 hours.

Who are the people who help you get things done, and how do you rely on them?

Melissa Strype is the only person I trust right now and her sister Shayna.

How do you keep track of what you have to do?

I believe in my heart that if it’s important I’ll remember to do it without needing to write it down, but this also leaves the people in my life, as the British would say, “very cross with me”. And involves me on the phone with GEICO every month begging them to renew my insurance policy free of penalty.

What’s your least favourite thing to do, and how do you deal with it?

Filling out forms of any kind, not well.

How do you recharge? What do you do when you want to forget about work?

I bathe. And I drive down this forest-y road near my house that doesn’t look like it’s in Los Angeles and I pretend I’m in Massachusetts.

What’s your favourite side project?

I’m making a song called Nightrider right now about a PT Cruiser.

What are you currently reading, or what’s something you’d recommend?

Naked Lunch, but I don’t understand it so I keep switching between that and a coffee table book of Prince photos.

Fill in the blank: I’d love to see _________ answer these same questions.


We’ve asked heroes, experts and flat-out productive people to share their shortcuts, workspaces and routines. Want to suggest someone we should feature or questions we should ask? [contact text=”Let us know.”]