Hailing from Massachusetts, Fleming, 34, got his start in the Boston comedy scene while still in his teens, growing his fanbase with the cult Youtube comedy series Gayle, in which he played the energetically unhinged suburban spitfire Gayle Waters-Waters. His 2019 international stand-up tour, Boba Everyday, was postponed at the outset of the pandemic. Yet live comedy’s loss became the internet’s win as Fleming revamped his material for Twitter and Youtube, blessing timelines with songs about nihilistic tax accountants and impressions of U.S. senator Amy Klobuchar expounding on how she “knew Sheik was Zelda the whole time” with bottles of Zinfandel taped to her hands.
On March 23, Fleming is performing his new virtual show Chris Fleming: Through the Baleen; “I like the idea of me being in the belly of a whale just doing the show. Entertaining the krill, you know, it’s like I’m like a cruise ship entertainer, but for krill,” he says of the concept.
Here, Fleming talks to Sharp about masculinity, TikTok, and the role of the clown.
Often, creators grow ambivalent about the thing they’re known best for. Is that the case for you and your Gayle skit “Company is Coming,” or are you pleased it’s out there being an ambassador for your comedy?
Well, I think the most popular thing casts the widest net, which also catches the most annoying people who talk to you at the airport, so that’s my only issue! No, I’m really proud of that video. There were years where I was like, ‘Oh, I can do more than this. Why do people not appreciate anything else?’ But now that I’m older, I look back and I’m like, ‘Oh, that’s really funny.’ It’s the first thing we shot for the fourth season, and I knew that [the series] wasn’t going well, we had like no following. And I was like, ‘I really need to swing for the fences.’ I’m very proud of it.
When the pandemic began you were in the swing of touring your stand-up show Boba Everyday; how did you recalibrate your approach to work the face of lockdown?
I was planning on touring that show internationally, and I’ll write a show and then be like, ‘Oh, sweet, I have a show that works live and it’s really fun to do.’ So that was very depressing [to have the tour cancelled]. What I did was just cannibalize it. I either made videos of the bits, or released some of the songs, like ‘Sick Jan’ and ‘Boba Manifesto’ and a Sufjan [Stevens] song about nail clippers, and stuff that I really love doing live. I just released it all and it felt like I had truly nothing left. I had nothing left to my name because after I did ‘Sick Jan’ for some reason I was like, ‘Wow, I don’t think I’d ever want to write anything again. I love this so much.’
I felt really dull and just like, ‘I need to figure out what the fuck is going on with myself right now.’ So, I didn’t really start writing again until fall. You have to keep making stuff, unless you want to work in a tropical fish store, which I kind of do.
You’ve had some big hits recently, like your Klobuchar bits, which seemed to resonate with a wide audience. Do you think your comedy met more people where they were at this year?
You know, all of a sudden people were like, ‘OK, you can be part of the club.’ All of a sudden, you’re getting retweeted by people that completely ignored you for the first 15 years of your career. It’s all so arbitrary. But sometimes things shift randomly, and this year has been one of those moments for me. I mean, the Klobuchar thing, I’m very surprised about. Sometimes I make things and am like, ‘I’m going to need to take this down in two minutes, no one’s going to understand what the hell I’m doing.’ But after the second primaries with Amy Klobuchar, I stayed up until 2AM writing a whole screenplay about her. I don’t know why. She just really, really inspires me. Every time I see her in the news, I’m like, ‘I need to make a video in the next 20 minutes!’
You’ve said in previous interviews that the best piece of advice you’ve received was from Rick Jenkins of Cambridge’s The Comedy Studio, who told you that “Through clarity with your audience, even the most absurd idea can be accessible” — How do you interpret that advice and apply it to your work?
I went to school for theater and I found that a lot of the arts can hide behind abstraction. I think in stand-up, you can’t really afford to be over people’s heads because you need the laughs to survive. So, if you want to do interesting stuff and stuff that’s authentic to you, it’s just to your benefit to be as clear as you can because it’s not cool for people to not get it.
The media has a bit of a Millennial vs. Gen Z fixation right now, and in your own way you’ve played off of that in a recent bit – do you think the two generations have different senses of humour?
I think most of my audience is Gen Z, and you know, I think I think Gen Z is totally funnier. I mean, I just joined TikTok, and it’s so funny, I need to be prepared at the drop of a hat to just be sent to bed for the weekend by someone roasting me, like some guy being like ‘This guy looks like he’s into karate’ or something. It’s like, ‘Yeah. All right, take me home, boys. Yep. Yep. I’m done.’ I feel like Gen Z can handle anything and I feel like Millennials cannot.
In honour of the fact that you recently joined TikTok, I want to ask you a question that’s become a trend on the app to answer: What is the most benign and mundane yet absolutely unhinged thing that you started doing during the pandemic?
I have been doing a lot of very, very simple equations on my iPhone calculator. I used to do that in social situations, but now I just to do it by myself. There’s something soothing about math.
In the culture right now there’s a rift between people who think no joke should be off limits and those who think in fact comedians need to realize that there are lines it’s harmful to cross. As somebody who doesn’t flirt with offensiveness to be funny, do you feel outside this debate, or do you have your own stance on it?
I think the people that are like ‘Oh, you can’t do anything anymore…’ It’s like, those are old jokes, they’re hack jokes, someone has already made them. People who think that cancel culture has gone too far – I don’t think so. I think it forces you to not be a lazy writer, to keep coming up with original stuff. That’s why people would rather say [something offensive] is edgy, because it gets an easy laugh and it’s much easier than having to actually come up with a unique thought. And if you’re not talking from your experience, and you’re also hurting people – what are you doing? I am quite careful. I really don’t want to upset people because that’s not the not the role of the clown. I don’t think of myself as a thought leader. The whole freedom of speech thing is such fucking bullshit.
Some of my favourite bits you’ve done riff on how uncomfortable and baffling you find conventional manhood – I’m thinking “Wildly Unlikeable Guy,” “Adventure Dad,” “I’m Afraid to Talk to Men.” What about masculinity makes it such a rich source of comedic material to you?
I think struggling with it myself. I think that’s just my therapy. Writing about it.
They say masculinity is a prison – do you feel a kind of sympathy for people who can’t see beyond it?
Oh, big time. ‘Wildly Unlikable Guy’ – if you spend enough time with that kind of guy, you do kind of love them in a way. And I almost feel protective of them and like, don’t want other people to see that they’re not good. So, yeah, there’s certainly a lot of love there.
Where do you want to see your career go from here?
I really hope things open up so I can do live performing again, I very much need that right now. I’m going crazy without doing that – I didn’t realize how important it was. As much as I feared doing it, I’m kind of lost without it.
Chris Fleming’s virtual show Chris Fleming: Through the Baleen is on March 23, 2021, 5PM PDT. This interview has been edited for length and clarity.