HTLA- Episode 54: How I Got Started Comedian, Ashley Ray

Ashley Ray  00:00

LA to me is for writers. Like, I have done more writing in this city than maybe anywhere else in my life. [laughs]

Brian De Los Santos  00:06

[music in] I'm Brian De Los Santos and this is How To LA.

Brian De Los Santos  00:20

[music swells] The City of Angels is made up of some pretty exciting people from all sorts of backgrounds, with all kinds of interests. We're not just talking about arts and entertainment here. There are folks who make LA's culture and whole vibe unique, whether they're making music, or movies, or pushing for social change. I want to put the spotlight on some of this city's most remarkable people, folks I think y'all should know about, and demystify how they got to where they are in life, from musicians and actors to change makers and comedians. We're kicking off the New Year by sitting down with some dope Angelenos and getting into it. So, here's a new segment we're calling "How I Got Started." [music swells] Our first chat is with the fabulous Ashley Ray. She's a stand-up comedian, a podcast host, TV writer, and television critic. Originally from Illinois, she's lived and worked in LA since 2019. In her few years here, she's become a true Angelina, settling her neighborhood in Frogtown, and getting some traffic shortcuts down. [music out]

Ashley Ray  01:26

[outdoor ambi] [laughing] We're just people like- Hey! [Employee: I'm Spencer] I'm Ashley. [Spencer: Ashley?] [Spencer mumbles] Yeah, we're just gonna hang in the lobby and- do this interview.

Brian De Los Santos  01:26

We met up with Ashley at the Elysian Theater in Frogtown. It's a short walk from her place and she's been working on standup sets here regularly.

Spencer  01:40

[outdoor ambi] Did y'all wanna go in the theater to do it, or is the lobby cool?

Ashley Ray  01:52

Uh, what do you think? [Brian: Whatever you think is best.] ...in the theater? [Brian: Yeah, sure. I've never- I've never been here actually.] [Ashley, Spencer, and Brian speaking at once]

Brian De Los Santos  01:58

We take our seats [music in] in the little black box theater and talk about how Ashley got started in a field that isn't always friendly to queer Black women.

Ashley Ray  02:06

I started stand up in Chicago, and the best part about starting in Chicago is you can go all over the Midwest and the South. It's so easy to tour. You know, you can take trains, you can drive. Uh, so I would do shows like across Indiana, [music out] and Michigan, [laughs] and Wisconsin. [Brian: Very white.] Yeah, very white, and I think it makes you a stronger comic. I think it also makes you bold because there were times where I- You know, you're walking into the room as a Black female comic and if you're in a place like Indiana, Michigan, there are gonna be people who immediately are like, Women aren't funny, and Black people are just woke. This is just gonna be a unfunny woke person, and I hate it. Like before you even- They, you know, they just see your face on a poster, and [laughs] that's like what they assume, and so it's fun to sometime, you know, to prove people wrong on that, to make them laugh. Like you see kind of, the stubbornness melt off of them. [laughs] Growing up, I was always like, the only Black kid in the room. Like, it was always just me. My mom, sort of at a certain point in my education was like, I'm gonna send you to, like a private school with a bunch of white kids. I got a scholarship. [laughs] Uh, but she was like, I want you to know how to be around these white people, like don't let them [music in] intimidate you.

Brian De Los Santos  03:19

Ashley had always been a creative kid. She loved music, and improv, and spoken word, but when she got to college she felt like she had to focus on grades, and get ready for the practicalities of the real world. And then-

Ashley Ray  03:32

I- I just slowly started to break, like I just was losing it.

Brian De Los Santos  03:36

Ashley knew she had to keep performing and doing comedy. [music out] She managed to balance stand up with a job in media, but it was a hustle. Like, literally three different jobs.

Ashley Ray  03:47

[music in] I was able to like, get a job at The Onion writing commercials and stuff, and that was like when I realized- Oh, I actually can do like, comedy writing. I can like, use my degree, and do something and also still do like, sponsored content, and the boring stuff, [laughs] and have like, a real job. I was also doing TV reviews for The A.V. Club. I would wake up in the morning, uh, write my reviews of either Blackish, Insecure, Scandal, whatever. Uh, go to my nine to five job, get off at five, go straight to like, Cole's, which is the legendary Chicago open mic, so I could get my name like, first on the open mic list. I would hang out there like, all night. Do as many sets as I could. I would like, do my set at Cole's, go to another show, go to another open mic, go to a showcase. Do like, three in a night because you can do that in Chicago. You cannot do that in LA. [laughs] And then I would like, go to bed at midnight, and wake up at five in the morning, and do it all again, [laughs] and [stutters] like, I didn't hate my life. [laughs] I was doing all of that, and I realized I love doing this. I felt so lucky and happy, and I just kind of kept it growing from there.

Brian De Los Santos  04:50

So, how did she get to LA? [music out]

Ashley Ray  04:52

I worked at The Onion for like two and a half years, and at a certain point you- We, we could tell Univision was- They were gonna sell it. Uh, cuz this was during like a lot of upheaval in digital media, and I knew they were gonna sell it, and there were gonna be a lot of layoffs. I applied for other jobs, and I got hired at Google, and they were the ones who were like, Oh, actually, we have an opening in an LA office that we would love for you to take that position, and I had already come out to LA a lot. I loved it. I knew I liked it more than New York. I knew that I wanted to be focused on TV writing, which LA is better for. I had friends here already. Like, I kind of had done some shows in the scene. So, I knew some people, and I said yes to the job. They moved me out here. [laughs] I worked at Google for like three years, and the whole time I was also like, touring and a performing stand-up comic. [laughs] [music in] I would like, do these client meetings all day, and get out, and then go again. Just do as [laughs] many shows as I could. [Brian: I love that.] Just like, dressed in a business suit. [Brian laughs] Like, yeah. Like, as I just came from, you know, Chelsea Market doing this deal and now I'm here to tell you jokes about boobs and cum. I- I remember one of my coworkers saw like an ad for me performing at some theater, and she was just like, Wait, is this you? So, I- It felt like I was living this kind of double life, uh, that could only last for so long. It is demanding working at Google and at the same time, uh, I was doing more stand up. I was like, touring all over. Um, in 2021, I got like, the HBO Max queer comedian special, and- li- [laughs] like, the- When I went to shoot that I like, had meetings at Google all day. [laughs] [music out]

Ashley Ray  06:31

[audio clip] Like my friends would be like, Ashley, like, where you get your coffee? It has to be ethical. Where you get your news? It has to be ethical. Even where you get your porn!? It has to be ethical. You know what I would do? I would make my own porn in The Sims 3. [audience laughs] You can't get more ethical than that. I'm an unproblematic queen, I know. Thank you.

Ashley Ray  06:54

I started to just kinda make enough from stand up and writing. I started doing more, basically consulting and just actual TV writing. I got hired on my first show, Alabama Jackson, uh, for Adult Swim. Uh, with Wanda Sykes and Donald Faison. It was great, and it had one season. You can watch it on YouTube, and it got cancelled, and we'll probably never make more. I was a staff writer, and you know, I- I feel like it's rare to get those kind of opportunities when you've been in LA for like, two years. Um, so I just felt so lucky. [laughs] You know, like, I just felt welcomed in LA in this really, kind of exciting way. And from there, I- I guess I've just kind of kept growing. I'm always looking for fun things, and in LA [music in] you get that. I think, you know, the question for most comics who come up in the Midwest is like, New York or LA? And I knew LA. I've- New York is good for stand up, but LA to me is for writers. Like, I have done more writing in this city than maybe anywhere else [laughs] in my life.

Brian De Los Santos  07:54

Give me like, the feeling when you're like- Hey, Mom. I made it. Or whoever you want to say it, like- Hey, dude. I made it. Whatever. Yeah.

Ashley Ray  08:03

Definitely my mom, yeah. [Brian and Ashley laugh]. Definitely my mom. I think a big moment was- I started like, in Chicago as a comedian, as like a TV critic, a writer just dreaming of wanting to write for TV, and one of my first gigs was reviewing Insecure, the first season when it debuted. [theme music to Insecure: ...Yeah. Why you gotta be so insecure? Yeah...] And over the course of the show, I moved to LA. Like, it was probably the second season I moved to LA, and all of a sudden I was here like where Issa was, and I was driving, and I would watch and be like, Oh, I know where that is. I know where that is. And I've- I started to feel very like, Oh, I'm in LA. And I'd reviewed it all the way through to the end through the last season for The A.V. Club, uh, and after it ended Issa Rae sent me an email and- [laughs] [Brian: Oh my god.] Right!? I tru- [Brian laughs] I truly like, I remember getting the notification on my phone and just turning my phone over like, That is- That's a prank. That isn't real. I misread something. And yeah, she sent me an email that just was like, I want to thank you for your grace over these seasons. I want to thank you for understanding the show. I think a lot of traditional media was still really stuck in focusing on like, white-centered stories in media. Like Fleabag and Girls got so much attention, but Insecure was never treated in the same way as like this kind of, high-end premium show. And it was, and that's how I approached it, and just to see that she saw that and appreciated it- That to me was like the first moment of like, Oh my gosh, okay.

Brian De Los Santos  09:40

We gotta pause for that [Ashley laughs] real quick because that is a moment for me. I'm just like, Oh my god. I'm getting emotional just thinking about how you felt because I also like, I'm from LA. I'm homegrown. Um you know, Insecure for me, and like watching it with my boyfriend, and watching with other friends was like, this is to me- This is the LA that I have experienced. [theme music to Insecure: ...Why you gotta be so insecure? Yeah....] And I love talking to you because you're not from LA, but you capture LA, right? You're creative. Um, I feel like you also in your comedy, you've opened um, yourself up to just being yourself, and I think what LA brings to the table. It allows people to be unapologetically themselves. [Ashley: Yeah.] And I think that's what you bring to the table.

Ashley Ray  10:25

I came here, and I just loved it, [laughs] like right away. I- I truly don't understand the people who don't love LA. [laughs] [Brian: Thank you for saying that.] I just- [Brian laughs] I'm sorry to you out there. I don't understand you if you don't love LA. I just- I think it's so beautiful, and special, and different, and there's all these little communities where it's almost like, if you can't find yourself like, walk a few more blocks. Like, [laughs] you'll be in a completely different place. LA is such a great place where you can find your space. Like, as a queer woman, a Black woman, there's like Tao Comedy Studio. There's places like the Elysian that are so open to promoting different kinds of performers and letting you find yourself, you know? I did my hour here and was just [laughs] basically like, I want to try this hour. I might record and like play around with it, and they were like, Yeah, go crazy. Here's the stage. Those opportunities are out there, and it can be intimidating, and it can feel hard, uh, but you just really have to like, reach out and put yourself out there. I respect LA too much to be like, I'm a real Los Angeleno [laughs] because I, I think you have to work for that. You know, if I- W- when I have my kids here, then I'll feel like I'm a real Los Angeleno. [laughs]

Brian De Los Santos  11:35

Okay! Well, we'll check in with you when that happens. And we'll [Ashley: Yeah. Yeah.] come back to you, Ashley, but- [Ashley: In 10, 12 years.] [Brian and Ashley laugh]

Brian De Los Santos  11:41

[music in] And as we wrapped up our chat, I had to ask Ashley if she had any LA pro tips she wanted to share.

Ashley Ray  11:52

If you're- If you're on the 101, and you're goin', you're goin' south, and it's that scary part where it's like the Wilshire and 6- So look, I g- it's- People get so scared and they're like, This is the most terrifying thing about moving to LA. It is not hard, okay? [music out] If you get stuck in that far right lane where you're like, I have to get on Wilshire-6, you can get back on the Harbor Freeway! There's another, there's another- Like just- You're- You'll be fine, and actually, if you're getting on the 10 after that, you're- You should do it anyway because then you'll already be in the right to get on the 10. [Brian: I-] It's not scary. It's really- It's not complicated.

Brian De Los Santos  12:30

You said earlier that you're not really an Angelina yet. I think you are cuz you just gave everyone [Ashley laughs] a super-secret tip.

Brian De Los Santos  12:39

[music in] That's comedian Ashley Ray. She performs regularly at the Elysian Theatre. You can check out her newsletter and podcasts and all sorts of other work at LAist.com/HowToLA. And we'll be bringing you more interesting people every few weeks. So, stay tuned, don't forget to subscribe, and we'll see you later. Bye!

Brian De Los Santos  13:11

Support for this podcast is made possible by Gordon and Dona Crawford, who believe that quality journalism makes LA a better place to live. This program is made possible in part by the Corporation for Public Broadcasting, a private corporation funded by the American people. [music out]