Episode #396
Kylie Brakeman is an actress and comedian who broke through during the pandemic, as millions have found themselves laughing and sharing her videos where she faces the camera as one of many high-energy characters just trying to make sense of the world we live in now. From the strength of her videos on Twitter, Instagram and TikTok, Brakeman has landed writing jobs on Peacock’s The Kids Tonight Show, as well as the Discovery Plus series Kicking & Streaming. Brakeman is showcasing her character live and in person at the 2022 Edinburgh Fringe Festival with Kylie Brakeman Presents: Linda Hollywood’s Big Hollywood Night. But first, she sat with me to talk about her life and career thus far.
Here’s a taste of Linda Hollywood for you:
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So tell me about Linda Hollywood, because she’s probably someone who — people who follow you from Twitter or Instagram or Tik Tok may have been introduced to Linda Hollywood, but maybe not.
Yeah, so basically I’ve only ever done like one video with her. She’s just like an agent-producer just general Hollywood cartoon type, driving down Sunset Boulevard, taking calls, saying like absolute showbiz gibberish. And, at first, the show sort of started out with her as an anchor, just as a way for me to showcase other characters, like OK, she’s a fun rock and host to come back to each time. But as I started developing it, it became more and more about her, and really diving into, OK, yeah, she’s a cartoon character and she acts this way and she’s like, very Hollywood, but those people do kind of exist and what is their deeper underlying problem, and who would they actually be? There’s still a lot of characters in the show, but they’re more axiomatically tied to her and her world. There’s a lot of new stuff. And so, it’s both things that I was doing before the pandemic onstage, that are just goofy, and then there are some that are adapted straight from videos and have been worked out for the stage. So it’s kind of a whole mix. I’m throwing shit at the wall and seeing what’s sticking right now. I’m having a blast.
You brought up a few things that I want to follow up on. The one thing you didn’t bring up is: You grew up in Hollywood or Hollywood-adjacent, right? You’re from Pasadena?
Yes, I am Hollywood-adjacent.
So how much has growing up in the shadow of Hollywood influenced or colored your perspective on show business?
Yeah, I think the proximity of course, it definitely does inform a lot of that and my parents — my mom (Kristen Hansen Brakeman) produces award shows and live variety shows, and my dad works in commercials. He does sound for commercials and he’s also been an actor and an improviser (EDITOR NOTE: Forrest Brakeman was part of an improv duo with Greg Proops!) and stand-up and all that. That’s their world a little bit. And so I was kind of raised on this lingo, and they’re not those types of people at all. Like there is the whole Hollywood working-class sort of genre of person that isn’t this. But definitely, being exposed to that and being exposed to that sense of humor and that sensibility was a huge influence on me. I also watched a lot of 30 Rock growing up and so that was another big influence on me. And I was like, Why aren’t these kids on the playground laughing at all these jokes about writers room? Why don’t they like this? And so, yeah, definitely being immersed in the world a little bit, and I still feel like an outsider. I haven’t like done that much. I don’t have that many credits, but just being around these people, it’s a constant source of inspiration. And I find the world so funny.
Funny that you would think of yourself as an outsider, because you grew up in Pasadena, but then you also went to college in LA, right? You went to Occidental. Then after Occidental, you went into UCB? So you were born and raised in the system.
It’s true. I just haven’t fully clawed my way yet. Is how I feel. It’s this weird feeling where the Internet has put me on this level of visibility that I definitely didn’t have before. But I sort of feel like I cheated. You know, like, I wasn’t on a show and then got 100,000 followers or had this long writing career and then people knew who I was. It’s like, I skipped a step. And now I have to prove it.
Well, you skipped a step, but then in some some ways you didn’t. Tell us what your career was like before the pandemic. Because you graduate from college. What’s it like trying to break into UCB in 2018-2019 when it’s already become this pipeline that everybody — not just people who grew up in LA, but everybody — is converging on L.A. and trying to get into the Franklin theater, trying to get into the Sunset Theater, both of which are closed. What was it like in those last couple of years at the UCB to try to break into the system?
I graduated in 2018. And then I was truly just bumming around, waiting for something to happen. Working in all these restaurants. And then in 2019, I got on a Maude team and then Characters Welcome and then a House B team: Mess Hall improv team, which is not Harold Night. It’s like where they put all the people who they were like, you might be able to do this at some point.
Did a House B team get a slot in either the Sunset or Franklin theater?
They got slots at the Sunset inner sanctum, which was their sort of Cafe space.
So you’re like performing to the people who are waiting to see the better show?
Yeah, yeah. It’s for the people who couldn’t get into ASSSSCAT. They’re like, you can go see Mess Hall over there and watch a bunch of people just like really trying to do the math in their head of what a Harold is. But it’s technically a house team. And so I was on three teams at once. Just kind of like walked right in, in a way. Like I did classes, but I was shocked at how fast it happened. But it was great. And I did feel like it was kind of oversaturated by the time that I got there. Like I’m told the prime time of UCB, where you could get a writer’s job from it or like, get opportunities from it was like maybe a few years before that time. It definitely felt like a bottleneck a little bit. I was emailing hundreds of reps just like ‘Hey! I’m on UCB teams now. Do you want to talk to me?’ And they did not care. That was not, didn’t really help that much. I met with a couple people right before the pandemic, like March 10. And then I followed up and they were like, we’re having Coronavirus. So we’re not going to talk to you right now. But yeah, then I started posting videos, just sort of as a way to prove to myself that I was still doing something and trying to create a sort of like visual resume, to send to people and be like, This is my body of work. I know that I’m not onstage anymore. I don’t have that theater endorsement of like a house team. But I am still working on stuff. And I never could have predicted this.
You have videos that predate the pandemic. Videos of you doing stand-up, there’s there’s videos of you doing sketches onstage, on video, Characters Welcome stuff. You had like the makings of a reel before the pandemic.
I did. I think it’s just this specific style that was like the right place at the right time. Because I mean, the sketch stuff that I was doing before then was very, like three-camera setups and it’s edited and there’s a setup and then you reveal the game and there’s then you beat it out, you hit it and then you get out and it’s three minutes. But now, that just is not what people wanted to see anymore and people wanted it to be like very stripped back, very lo-fi. It was this weird time where I think we’re out of it now a little bit, where like people just wanted to see your friend on FaceTime doing a bit, essentially. They didn’t want to work. The attention spans got so short where nobody could even watch through a setup anymore. You have to set it up in the in the caption and then deliver it like immediately or else nobody cares.
Right. I remember there were before the pandemic, front-facing character comedy was starting to become a thing in 2019. I remember every year Jason Zinoman, who’s the critic at the New York Times, he and I do a year-in-review kind of thing. And I remember at the end of 2019, we were talking about the rise of the front-facing camera people and at that time there were only like a few people think like Eva Victor was one, Alyssa Limperis was another.
Natalie Walker was the first person I saw, where I was like, oh, you can do that?
You just mentioned Natalie. What had you seen out there that made you go oh, I could do this without having a stage or a crew?
I think it was probably her. I mean, pretty much everyone you mentioned. A lot of those people started posting at the same time I did or that was at least like when I noticed them. I think there was this like, really golden time window where everyone was at home and so a lot of those people shot up at the same time.
But yeah, I just thought they were so funny. And I was like, well, I can’t really get together with people and write something and shoot it so I’m gonna do my best and I had done like, one or two videos that were front-facing before the mask one went super viral. And they got like a little bit of traction. My friends really liked them. And so I had the smallest bit of confidence to keep going, but I shot a lot in those early days of the pandemic that I didn’t post because I was like, this is horrible. But I eventually found it and I’m glad that I had quality control for at least a little while.
But how did you have that quality control? Was it all internal or did you run it past friends?
Usually most characters start with like a phrase that I think is funny. Or just something I’ll be saying to myself in the shower or in a car. And then I’m like, OK, well who would this person be? I think the mask one was me kind of going for clickbait in the way that I’m like, I don’t think I’ve seen anybody do this concept. yet. I think Blair Erskine did it like the next day or like a day before. And so it was like, it was starting. And of course everyone’s done it now. But I was like I bet. I bet this could be something.
The pandemic lockdown started in March 2020. And your mask video, that wasn’t until July. So that’s a few months of you being holed up without an outlet, experimenting.
And then a whole bunch of May and June where it was just like, the protests were happening and there was police outside our house every day. The helicopters were going crazy. Like it just felt really apocalyptic. And I think the tone of everything online was a very justified reckoning and everything and so I wasn’t making anything. I wasn’t doing any of that. And it slowly became like, OK, people are posting content again. There was another window. Yeah, it was it was it was just a scary wild time. I can’t believe the police shot something that was very scary. And I almost got trampled by a mob. And I’m like, wow, we’re going zero to 100 very fast.
That’s one of not-so-secrets of your successful videos is they go from zero to 100. Like the art of the jump-cut. A lot of your characters, you mentioned in the beginning with Linda Hollywood, that you’re drawn to these kind of spiraling characters and each one of the front facing videos that’s become really popular has that element to it.
Yeah, I think when I eventually got in the New York Times, they described me as a high strung Yankee, which was like, I had no idea. Because I feel like I’m self aware. And I feel like I know what my comedy is. But then I guess through the internet, I’ve learned that I’m manic and that I’m loud. I never knew that that was the label. But like looking back, I’m like, oh, yeah, that makes sense. Everybody’s high-strung, everybody’s at their wit’s end. Everybody’s like just a wine mom who has had enough.
Part of that is editing, though.
Yes, the jump cuts are a comedian’s best friend. Because even if you don’t write a joke, if you put a jump cut, if it cuts fast enough, it sounds like a joke. And so it’s a little bit of cheating.
How long did the mask video take?
To put together, about an hour.
Did you have it all written or were you did you have some outlines, and you’re like, I’m just gonna riff and see what sticks later?
I had like five lines written, and then I just kind of went out to our garage because I was self conscious. I didn’t want my roommates to hear me. And we were sort of living in this giant like, crazy cheap house that we got on this wild deal. And so we had this like haunted condemned garage where I filmed most of my videos in 2020. I just kind of sat there and just started talking. And yeah, I usually improvise about half. Usually, the improvised ones are a little better because they’re a little looser and a little less like stiff.
How much of it did you find that you wanted to keep vs. how much you’re like, oh, no, that’s garbage. But these ones are good?
Yeah, I think the earlier videos I definitely shot way more. I think like over time, I was able to do it in less. Like I knew how much to cut and then also the amount of time that videos lasted. gradually went down. People stopped watching things that were more than a minute 30 seconds, and then now it’s nothing I post is longer than 45 seconds. So eventually we’ll just be back to Vine. We just keep reinventing the wheel.
It’s funny you say that because TikTok is going in the other direction, lengthening the limits on their videos.
YouTube videos are 35 minutes now.
But they’re also shorter?
That’s YouTube shorts, which I can’t figure out. I don’t know how to succeed on YouTube. I’ve tried for years.
Although fun fact: If you look up your IMDB page, your shorts are all listed.
Someone went through and put me as the executive producer of Why I Won’t Wear a Mask and I cannot figure out how to take it down. I tried to take it down. I think my manager tried to take it down. I don’t know. I guess it’s there to stay.
You mentioned filming that in a big old house with roommates. What was their reaction when that blew up?
I think they were just kind of fascinated by it. They don’t do comedy. So I was kind of like that token friend who was doing weirder stuff. And eventually they were just like, OK, there she is. She’s filming her videos. But I’m glad that they did well, because that was a justification for like, OK, no, she has to do that, because she’s got external validation from it. They were very supportive.
What was the immediate impact of going viral? Was there one other than gaining followers? Was there any like tangible impact in terms of your show business career?
Yeah, well, I went on a lot of panic walks because I just kept watching the numbers go up and up and up in a way that was just like, jarring. And then I did get representation from it. I got a lot of interviews with podcasts and websites and stuff like that. And then I interviewed for a few shows to write. And then it’s just kind of like, a general visibility thing. People reach out to offer you things. more easily now. But to write for The Kids Tonight Show, which was like a spin off of Jimmy Fallon’s show, but hosted by 10 year olds. It was very cute. It was a very adorable time. But yeah, it’s been great. There’s just like a lot. It’s this new category of visibility that I definitely didn’t have before. And I was just trying to work out and I know that like if the pandemic hadn’t happened, and if I was still at UCB, I would probably still be in the same place careerwise, because it just seemed like the well had dried up over there in terms of opportunities, because there were so many talented people.
Did the Kids Tonight Show film and work in 30 Rock?
That was in 30 Rock. Yeah, so it was it was just, it was amazing. And it was my first time in New York and I got to live there for two months. And it was very like, girl from a small town is in New York City. Even though the town I’m from is Los Angeles. I still felt that like, whoa! the buildings are so tall, like tiny girl feeling.
But as you’re writing for 10 year olds, but you are describing yourself as a 10 year old, quoting 30 Rock, so it’s kind of comes full circle, right?
It’s full circle. You never expect it.
But you also wrote for a series called Kicking and Screaming.
Yes, that was a Discovery+ show with Grace Helbig and Mamrie Hart.
I know both of them from before they became YouTube stars. Did you learn anything writing for them and working with them in terms of how they have been able to pivot and parlay their internet stardom?
I think the main thing that I walked away from that with was, how they had a very specific style of improv and riffing off each other that was just like, perfecting the art of this YouTube reaction thing which I think people don’t always consider. But they were so efficient at getting it out, and because so much of it is that, like there were scripted parts that I wrote, but they were just so good at bouncing off each other and knowing what they had to do to get it done.
You mentioned recently on Twitter that in 2022, you’re posting more videos on Instagram versus Twitter, because it helps your career more to be on Instagram. I know that you’ve also done stuff with Cameo and Patreon. So just from the business side of being an internet comedian, how has that changed just in the last couple of years like where the business is?
I can make money on Instagram just by getting bonuses. It’s not a lot at all. I’m not rolling in it in any way. I can’t pay my rent with it. But it does, having more followers on Instagram. I’m learning like, if it puts you in front of brands. You can’t really do Spon-con on Twitter as much. Twitter doesn’t really have much in terms of monetization at all. And TikTok, I was on the Creator fund and then I got off of it and then my views went up, so I’m like, I guess I just won’t make money on this thing. But I think it is like a visibility like ability to get yourself in front of brands type thing that helps you on like a monetary level. I think that Twitter is still good for career stuff because I think a lot of like Hollywood people are on Twitter, but it’s a different type of video that succeeds on Instagram and sometimes TikTok, as opposed to Twitter. I feel like on Twitter, people don’t really want to see something that’s not cerebral low effort. I think on Instagram, you have more freedom to be a little louder, to be a little more broad and to do something that’s like a little more sketch comedy, as opposed to Twitter videos, which I still try and do. I’m just trying to follow what’s fun right now because I have the followers and so I just want to have the freedom to just post whatever I want creatively and not worry about like, Oh no, my views will tank if I do this, because now I at least like have the established people. So it’s a good place to be, to be able to throw out stupid things. And somehow 100,000s of people still see it.
Yeah, you just had another one about a screenwriter date?
Yeah, yeah. Henry Typewriter. Man who talks to you at Starbucks.
Of course, you had that intentionally viral Tweet asking if anyone would be willing to watch Star Wars for one hour for $1 million.
I can’t believe I did that. There was one day where I was like, I’m going to Tweet in the style of those viral Tweets that get 200,000 likes. I Tweeted like 20 Tweets that day that were all just in the style of like: ‘That feeling when socks are warm > > > nothing.’ Just real clickbait-y. Like the most basic things you could ever Tweet. And that Star Wars one. I got so close. I got 150,000 likes. I was like, there is such a chance I pull this off. It was one of my proudest moments. I’m like, This is nuts.
Do you care at this point if something really hits or if it just pleases enough of your friends?
If it’s something that like I, and luckily, there’s usually a correlation of, if there’s one that I really believe is good and funny, it usually does well. But there are some that I’m like, OK, I’m just throwing this one out there, and then it’ll get the standard amount of people who will typically respond. So it’s kind of a freedom thing. I know that something will never like tank tank anymore, which is kind of good kind of bad. But yeah, I think most of the time what I find funny is like is going to do better.
Has your attitude changed on that? Because at various times you’ve been involved with Patreon and Cameo, which can feel like more like doing art for commerce’s sake. The business part of show business. What was your experience with those platforms?
Cameo, I think was more effective for me when it was still COVID — still, the feverish nature of the Trump years and it was a lot of people just being like, Can you do the Trump robot to my dad? It’s good and every once in a while, I still get them sometimes. Cameo did pay my rent for a few months in 2020, which was good. I never expected to be able to like actually make money doing it. Patreon I never got the hang of. I think I just felt guilty taking people’s money after a certain point, even though I didn’t have a job. I was not doing financially that well, but I just I think I have this weird thing where I’m like, I can’t — ultimately I could go live in my parents house if I absolutely needed to. I can’t take your money.
And to bring it all back to where we started talking about Edinburgh, preparing to do a monthlong run of a live show. How does it feel? Knowing that most of the people who come to see you will only know you from these short jump-cut bursts that you can’t quite replicate in person, or can you?
Or can you????!!! That is the question. You can’t.
You can’t speak that way for an hour?
I can’t keep it up. But yeah, it’ll be interesting because they’ll get to see a different side of me. The side that I started with and the side that is more, a slower pace. And more like setup, reveal, game, keep going, character stuff that’s — it’s just so much different than what’s online. I went to do a half-hour version of it, just the very beginning of testing it out. My boyfriend’s in a sketch group called Business Casual and they do shows as well. They and I split a bill in Albuquerque, which is a place I’ve never been, but I got like a lot of people from Instagram being like hey, so great to be there, so great to meet you, so great to see the show and it just really, I don’t know, it just touched me that someone would watch my stuff and like it enough to show up in person. I think it’s also a very L.A. mentality of like, nobody wants to see shows here. In theory you do. You say, oh yeah, I’m coming! Come to my friends show. You’re absolutely not. You’re not driving there. Wherever it is, you’re not driving to it. And so to be in an environment where everyone is specifically there to see shows, I’m very excited. I’m very curious to see what will happen. I’ll be interested to see if it shows up. If the audience translates that if they hate it or if they’re like yeah, that’s what we expected from you.
So how have your own expectations for your career changed since you graduated from college?
I’m definitely harder on myself now. I think there’s also just like this, this weird blanket realm of possibility thing, where it’s like, oh, if I worked really hard on that, I could probably do that. Or if I just put all my energy in this and it’s just this like, sort of endless options choice thing. And so you’re paralyzed by it. So you do nothing. I don’t know. I think before, my only goal in the world was to get on a UCB House team, and that was like it. If I’ll do if I do that, then that’s all I need, like ever. And then I did it. And then it’s like the floor is just raised every time, and then you get something and then you go, Oh, yeah, well, I expected this. I deserve this. That’s the absolute least I could do. But what I really want is this, and then you get that and then you’re like, well, that’s nothing because I already did that. And so I have to get something else. It’s really neverending but it is definitely like I feel like I want more from myself, if that makes sense.
It does. I mean, it’s a very human impulse to always want more. To never be fulfilled, which can be kind of sad at the same time. Can’t I just be happy with what I have? I can definitely be very happy with this conversation. So Kylie, thank you so much. I look forward to seeing you and your show and Edinburgh.
Thanks for having me.
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