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Creativity isn’t tidy—it’s risky, chaotic, and full of surprises. It’s full of breakthroughs and breakdowns, moments of flow and moments of doubt. Join Mishu Hilmy for unfiltered conversations with artists, filmmakers, musicians, and fearless makers who thrive in the unknown, embrace imperfection, and create at the edge of possibility.
This is your front row seat to the self-doubt, unexpected wins, and messy emotional work of making something real. But craft isn’t just about feeling—it’s about problem-solving, process, and the devotion behind mastery.
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Mishu Hilmy
Welcome to Mischief in Mastery where we embrace the ups, downs, and all around uncertainty of a creative life and that steady and sometimes not so steady journey toward expertise. Each episode we talk candidly with people I know, people I don't know, folks who produce, direct, write, act, do comedy, make art, make messes, and make meaning out of their lives. You will hear guests lay out how they work, what they're thinking about, where they get stuck, and why they snap out of their comfort zones and into big bold
risky moves. So if you're hungry for honest insights, deep dives into process philosophies and practical tips, plus maybe a little mischief along the way, you're in the right place. For more, visit mischiefpod.com. Hey everyone, it's Michio and welcome to Mischief and Mastery. Today we're talking to Ray Tang, a Chicago-based writer, photographer, filmmaker, and performer whose stand-up credits include the recent 2024 SNL showcase at the Annoyance Theatre,
as well as at The Laugh Factory, Zanies, and Hollywood Improv. Ray is a Comedy Gazelle Vouch finalist in 2024, and she's represented by Stuart Talent Agency Chicago. Every Tuesday she hosts Pizza Mike, a beloved Mike featured in the New York Times travel section. Ray and I talk about experimenting across comedy mediums, staying playful while trying to find some degree of creative sustainability as well as figuring out what it means to be enough.
in the field of creating art and comedy, as well as a bunch of other stuff. If you want to learn more about Ray, you can check out RayTang.com as well as follow her on Instagram at RayTangerine. I'll have all that in the show notes. Hope you enjoy this lovely and delightful conversation with a friend of mine, Ray Tang.
We're working on a podcast recently, very, very of topic. It's the right wrong radio hour. So it's just a comedy show. It's different in that it's been scripted. So a lot of it is like scripted work and it's like every week. So it's a lot of work, but.
Mishu Hilmy (02:12)
What inspired this how big is the team so it's all fictional I take it or is it auto you know like what's I mean you don't have to reveal the secret sauce but so you're writing it it's scripted but it's you know yeah what's that been like how's the team how who are the voice actors what's going on
Sure, we actually invite a different person every week to help us write and do some sketches. It's pretty much live, we're recording it. Like we literally record the sound of the Yeah, it's pretty fun. It's really a game of how do you crack each other up, which has been kind of nice and interesting. But yeah, the team is just Brayden and I. Brayden and I have been a sketch duo for the longest time, but we wanted a way to do sketches every week, but we did not want to do the work of actually putting together a sketch show.
Wow, interesting.
Rey Tang (02:59)
Because with two people, that's impossible. And so yeah, we needed some way to get reps. So we figured this might be the easiest way to work with and learn from a bunch of people that we really admire.
Yeah, I love hearing that. It's like really sharpening the saw of like, you can't be in production every time. You can't have a fully produced 60, 90 minute two person sketch show every month. You'll probably die from exhaustion. So you created a nice nimble tool of drafting up these sketches and then finding friends who want to pop in and is it like a somewhat cold read of it or is, you know.
It's pretty much a cold read, except for me. need to know where the tech is, so I kind of take a glimpse ahead of time. But mostly it's a cold read. I never really know where people go.
Right, and you're recording this live in a place or like live on a platform like a Zoom or a Skype or a Riverside?
We're collaborating with our friend Elaine Golden right now. We set up a little studio in her apartment. She has a three-bedroom apartment, but it's just her. So she wants a roommate eventually, but right now that third room, well, we've combined forces and it's been nice to have a little collective going.
Mishu Hilmy (04:10)
Cool. And live as in you're just doing it in one take, not live as in there's gonna be an audience of strangers sitting in this third room. Great, great.
For sure. It's recorded in one go. right.
Wonderful. And we know each other and I think I'm familiar with a fair amount of your work. So you do a lot in the comedy medium, stand-up comedy, sketch comedy, and you also do work acting and directing. So are you pretty medium agnostic? Like what's been the pull of just playing around with all these different mediums?
medium agnostic. I don't know. I think you could romanticize it and say, she's a multi hyphenate. I think you could tell the honest truth and be like, she's scared and she's just doing whatever is going to make it work. I don't know. It's weird. I have ADHD. So that's definitely one of it. I get trouble focusing on things. So it's fun to just be, I like being bad at things. So it's nice to, it's always nice to learn a new skill.
Yeah, yeah.
Rey Tang (05:15)
Right. I think I have started to get to a point where I'm like I need to start figuring out what I'm actually good at and trying to condense a little bit. But yeah.
Right, so it's like a mix of, I think there's like the spirit of experimentation and sort of the spirit of the kind of allowing oneself to be vulnerable and an amateur and not know, but it seems like there's also part of you that's wondering like what is best to like lock into. So with that, like, yeah, you'll be playing around with the podcast and maybe that'll tickle something and grow into something really strong, but do you find that there are one or two key creative experiences that have been the thing that you're, you're no.
your whispers in your heart say, come on Ray, just focus, focus a little more on this.
Well, let's see. It's got confusing. So I'm very, I think I'm very good at hosting in standup. Like I'm very good at making a comfortable room. I think standup wise, I still have a lot of room to grow, but I do think I'm pretty good at generating like a nice warmth for the audience. So that's one skill that I do think I'm like, okay, time to buckle down there of like figure out how to make standup a more marketable skill for me. But also,
Yeah, I don't know. The world's kind of big right now in that way. I honestly, I want to like double down because I think that's important, but also, but also I like doing everything. So it's tricky. It's a tricky time. This is what happens when you're 25 and mentally ill, unfortunately.
Mishu Hilmy (06:327)
Mm-hmm.
Mishu Hilmy (06:45)
Yeah, yeah, I think there's like a bit of balance and permission, right? And maybe it's, I don't want to speak in tridapherisms, but like to trust the process or trust yourself as an artist to go, okay, I've done five more years and I've done, you know, trying things and I imagine some will organically fade off, right? Like there's maybe a period where like, you know, I'm 34 and I don't think I want to do sketches, you know, anymore.
It seemed like ideally the most gentle status to go, this is where I'm at right now, rather than is it out of, you know, fear or is it out of just like, I'm okay with that. I'm okay with being a little bit curious. I'm okay with like expanding this network and just being in the shit with, you know, on stage or on a podcast or with this creative cohort of poets who also do funny poems and they're just great to be around. And for you, when it came to like, I think we talked about it briefly after a shoot. Did you?
come from like a UCB improv sketch or, know, did you enter comedy through sketch or improv? I think we were talking about improvisation or maybe it was IO. It seemed like you dabbled in a fair amount of point of views or curriculums when it came to like comedy. Is that what your entrance point was, at least with, you know, comedy as a form or genre?
Oh, yeah, I started with the annoyance. The annoyance, was my first place where I really studied comedy and started doing classes there. And I still deeply love the annoyance. I did take classes at IO actually. I kind of take classes wherever because if it's because there's a lot of diversity scholarships and I happen to be the diverse person. So I try to try to learn my education that way. But yeah, I
I started with annoyance. think I got, really got my feelings hurt with improv a little bit. And I don't think I realized how hard people worked at it or like how much it was of like, actually they started when they were in like high school. I didn't, wasn't on my college improv team. Like just sort of like.
Rey Tang (08:52)
I kind of didn't put into perspective. Now stand up, stand up was sexy to me because it was like, you can work hard at this, people are starting at all levels and like people objectively get better and it's more open about that. And so I liked that. But yeah, now I'm thinking about going back into improv because I kind of would like to get better at it. I think that's where my brain's at where it's like, okay, I might not naturally be gifted or God's, like
God's blessing upon man, but like I think I could I think I could make some fun make-em-ups Yeah, I think too seriously about all this stuff and that bums me out. But anyways
yeah. Right. What's a cash? I was talking to someone a few weeks ago. Take the work seriously, but not yourself. So, you know, yeah, I swear, like the things that you love, you love and care about it. And I think there's a delight in getting better and thinking about how you can get better specific to improv. Like, I remember being in a similar space when I was in my 20s of like, I was so bad and I was like,
taking multiple classes at the same time to try and figure it out because I was so, so bad. Yeah, yeah, yeah. It took probably me too. Six years of like grinding and doing basement shows and bar shows to get to a degree of like proficiency and a sense of fuck it. But yeah, I don't know. I think the love of audience is what drew me to improvising and trying to fine tune my ear of like what is
totally unacceptable for a human person to say in front of a group of strangers or do a group of strangers. And improv is a very fast way of doing that because you have a little bit larger audience, right? You can have the same experience with stand up, but stand up can at the initiate levels can be a little bit like you're entering a cave of nine grumpy depressed men. Yeah. And they'll not laugh. So it's really hard to attune your ear or your impulse.
Mishu Hilmy (10:55)
At least I think early on with stand up because you don't have, know, 12 people on stage can get a little bit larger of an audience than say nine people have been doing it for X number of years.
I think you're right. think improv is more of a welcoming space for beginners. Like it's just, it's so much easier to go at it, not alone to start. I kind of admire people who start in standup because it's really hard. Like you really, either you're very sociable and you can build that community early on or you like, you're just doing it alone and that's really hard to do. yeah, kudos to that. Yeah, that's never quite been my experience because I started with the improv background.
And I'm thinking about going back into it, so we'll see what happens.
Nice. Yeah. I guess the thing with improvisation is because there's there's the institutional element where I can see where it is a hurting experience because it's like, yeah, people are trying to enter and access this institution and are doing what they can or what they've done to get those reps to be sort of a fixture of an institution, whether it's Second City Annoyance, IO or wherever versus stand up. I think is a little bit more like skateboarding culture, even kind of punky in that.
You can go to as many number of open mics as you want and no one will know. But then eventually if you practice, maybe have a bit of self-awareness, you can, you know, send some tapes over to bookers and it's still like this always an institutional element, but I think improvisation has a home base that feels very, you know, are you in or are you
Rey Tang (12:24)
Yeah, you can't really start a band and improv. Like you could start your own group, but it's rare for like an indie group outside of one of the institutions to do like really good. Most of them are like built by like IO, built by annoyance. it's well not annoyance anymore, but you know what I mean? Like it's right. It's it's less of a DIY culture, which which is me. But but well, I'm getting back into it. And anybody's listening to produce a show. Well, I love this shit.
I see no problems with the improv scene.
how are you approaching 2025 differently in terms of what's the healthy capacity for you?
Mishu, you tell me, I don't know. think, you know, I mean, I go to therapy and we're always checking in about that. So I don't want put myself down too much. Like, I definitely try my best to be sustainable in my practice. but it's also
it's, it's not easy. I always tend to go overextend and then pull back, overextend and pull back. That seems to be my cycle.
Mishu Hilmy (13:30.478)
Yeah, I mean, I relate to that. think I've gotten a little bit more mindful of it, but I remember, I don't know, it's like a certain compulsion. So like, don't want to necessarily use the word compulsion, but like, do you find that you would, you know, you're sort of driven or there's a certain ambition that's really kind of like creating an anxiety or needs, but I gotta, I gotta just do this now. Of course. Yeah.
yeah, yeah, it's a very egotistical thing. get, there's a lot of jealousy in there, I think, that is scary. Like, this person's doing that thing, I gotta step it up. Which people have told me they feel that way about me in like a positive way. And it just always is like very interesting to me because I'm like, actually,
I don't know. I don't think we can keep... I guess it's positive in that we're motivating each other to create art. I think it's a little scary when it's like, we're actually burning each other out. I'm going to choose to look at it in the positive way. But anyways, yeah, definitely peer pressure. That's all big motivator. And obviously love of the craft.
Interesting. Yeah. Right. Yeah. Yeah. I think I don't know. I don't think we spent too much time talking about it, but I it took me a long time to create this arbitrary definition. But a lot of like my output was really driven by what I would call like insecure ambition, where it's like, I just got to do this because there's a void in my heart. And, you know, the the success of this thing will fill the void. And it's like, oh, no, it never it never got full and it will never be filled.
So like, yeah, you mentioned kind of the ego, but when it comes to this, this drive, like you're aware of, like you're creating comparisons. So like, how do you, how do you deal with that default or that kind of the impulse to be like, got to compare. I'm not like, I'm not at X level. Everyone started improvising when they were 16. I was in my twenties. Like what's, you know, do you, do you sense like, do you have a way of reframing that?
Mishu Hilmy (15:33.92)
experience that initial impulse of, shoot, I gotta compare myself to others.
Well, I'm surrounded by very good people in my life. That's probably the most important piece. I have a lot of friends who will just check me. I have a girlfriend who does not do creative work and she will check me. My favorite thing was that I told my mom once, said, I got onto a, this is a humble brag, but whatever, mom, I got onto a showcase for SNL. And my mom goes,
What's SNL? And then she went, I don't know what that is, but I hope you have fun. I was like, wow, that really, none of this actually matters. I surround myself with good people and I'm, don't know, man. It's a weird, it's a weird time. Have you read Daisy Jones and the Six?
No, I'm not familiar with that.
Okay, obsessed with that author. It's like these fun little summer reads of like, famous band, famous starlet, but Daisy Jones of the Six is about this like fictional band, but like, it really plays on the whole idea of like ego and like, the need to be great. And then like, the need to be different, but also how it's filling like a vacuum. And it's just like, it's cool. Cause like in the fictional piece, they're just like, at the end, end up like, yeah, I'm a dad in like, middle of nowhere USA. And it's like,
Rey Tang (16:57.038)
In my head, I'm genuinely kind of like, that doesn't sound that bad. I used to worry about being a sellout, it's like, it'd be nice to just do community theater and somewhere. don't know. Wait, am I allowed to curse?
Yeah.
Yeah, yeah, yeah, yeah, can eat shit, die and fuck yourself and all that good. yeah, yeah, yeah, yeah. I relate to that. I think maybe six, seven months ago, I read for the first time, The Courage to be Disliked, which is a dialectical or dialogic, Adlerian conversation. So Adlerian psychotherapy is about
Yeah, yeah, all the carlins.
Mishu Hilmy (17:37.774)
I think really about observations. It aligns with nonviolent communication to a degree, but basically the thesis that I walked away with is the courage to be disliked is to essentially eliminate the desire to be special. like you will eliminate sort of suffering if you practice examining how much your motivations are to become, to be special, to be seen as special.
I am great, I am special, am other versus to like just practice being okay with like yourself and your community and you know that the fact that you live in a universe of interconnected communities is enough. that's been something I was thinking about around like, oh yeah, the ego wants to be special. I want to be, you know, a successful one of the greats or whatever. And like kind of the Adlerian counterpoint is like what happens if you practice not
being special and just being okay. That's,
that's a big one. Well, I do, I love that. To be able to be disliked, to be okay with being disliked is to okay with not being special. I love that. I think that makes sense because everyone's not gonna love you. You are not a special exception. that, well, that hurts.
Yeah, it's like a point of view, right? It's point of view to adopt or not adopt, but I've been finding it an interesting exploration to like, yeah, where is my impulse? Like, oh, shoot, I guess I do things to be seen as special or kind of for sure.
Rey Tang (19:14.976)
I do a lot of things for cloud. It is. Yeah. Yeah. That is that is gorgeous. I think there was a point. This is truly a therapy session that I had like a couple of years back, which I was like this was when I was very keep in mind I was Trey Trey depressed, but Trey depressed. But I I did say the words to my therapist. If I'm not special, why am I here? And that was very dark.
Ready to press.
Rey Tang (19:43.754)
and was like very much of a thing like, I had tied my worth completely with my career and that was scary. I would not be doing that again. But yeah, yeah, there's, there's my roommate says something that really illuminated me. My roommate, his name is Nick Park. Great, great creative in the Chicago community. He said, do you really believe that people don't have worth if they're not successful? And I honestly looked at him and I thought,
I know that should be obvious, but I genuinely think, no, I've never thought that. Like I've never thought that way before. Weird.
Yeah, I don't know like whatever sort of cultural, you know upbringing social upbringing family upbringing media consumption like upbringing It's like these weird unexamined implicit points of views that can kind of just start creating a weird damage or a propulsion of like compulsive behavior
Sure. You know, Mishu, hold me to this. Hold me to this. I think my goal really in life is to not have a day job. To be able to creative work as money and like do the creative work that I actually want to do. Not like, cause like I, I thought about this long ago. Like I don't think I could like settle in another creative profession. Like I know a lot of folks do that and it's not selling for them. It's like they actually found a new passion. But like, for example, I don't think I could work as an accountant for a TV show. Cup.
Right. Or doing copywriting for an ad agency. I mean, you might evolve to that point if that was something, but that's also kind of an adjacent thing. It's not script writing, it's not improv, but I'm getting paid the high five, low six figure salary for writing copy, but it's for capital one.
Rey Tang (21:28.75)
Oh, for sure, for sure. No, that I don't mind, but I think my goal, my dream is to probably make this career sustainable somehow.
Right. Yeah, yeah. I think I mean, I align with that. And then the conversation I have is like, I guess I take that as like a really optimal romantic version and to be gentle with myself if it takes X number of years or never happens because there's a certain romance or underlying belief that like I am somehow better or this is something this form of money is somehow better.
Which I think it's better in the sense that it's like aligned with something that's engaging, meaningful, evokes positive emotions and was hard, it was an accomplishment. And at the same time, there's also something to be said that I try to remind myself of like, it's also enough to just like have a humble, a steady, steady day job and you know, squirrel away, you know, an hour on a Thursday at 7pm to talk to my friend on a podcast. Like that's also okay. you know, maybe that's
Bye bye.
But ideally, ideally, the romantic vision is I earn my livelihood off of my creative insights, but I'm still OK. I'm still enough, even if that's not the case.
Rey Tang (22:48.558)
Yes, yes, I think that's correct. I think it is, this is where my mind's at. I think that's, it's a harder notion to make money off of creative careers in Chicago versus if you were in the two big cities. Which is not a dig on Chicago for the love of God. I'm not trying to dig on Chicago, but.
Right.
Rey Tang (23:18.006)
I do think that's why in my head, and that's the sort of reconciliation I've been thinking about, like, I don't know if I can fulfill that goal. I think it'd take me, I think it'd be very hard for me to fulfill that goal here, but I don't know.
Yeah, I think so. think I mean, it makes sense, right? Like, people migrate to different parts of the world because there's more economic opportunity. And similar with industries, right? If you want to be in the oil industry, you're probably not going to make a living staying in Chicago. So I think there's some degree of honesty in that, you know, the bi-coastal, whether it's New York or LA and potentially even Georgia, you can get more steady work.
versus in Chicago, you're kind of waiting for one of the NBC shows that happen to be shooting at the Cinespaces or maybe you get like an equity gig at Steppenwolf, but even that's like, you know, you have to be on stage every night and you're probably only gonna get, you know, a three month play and that's probably you walk away with like $12,000 or.
Yeah, my acting teacher said that actors in Chicago feel a little more desperate because of the lack of opportunities here. That's what inhibits us. I think there's a lot of truth to it. And this is really interesting because I don't, I'm not shitting on Chicago. I'm just saying the infrastructure is not here yet. Like, I mean, I would like it to be more than anything, but you would, you have to put in a lot more work.
Is that fair to say? You put in a lot more work here than, I don't know, like you could get discovered in LA or New York. Like it's just a different game there.
Mishu Hilmy (24:58.028)
Yeah. Yeah. I this is a great time to be anonymous, to cut your teeth and develop your point of view anonymously without the pressure and the cost of living in New York City or Los Angeles. You can really take bigger risks and fail and explore what is your particular itch or your particular point of view is. But at a certain point, that decision is like, OK, I think I have like 80 percent of what I sense what I want to be doing is. Maybe I take a swing there.
There's just, you know, it's volume, right? There's more, I think this is like a mostly a luck-based industry. think skill and talent and hard work have their place, but I'd say there's a fair amount of luck and how, you know, work begets work. And if you have more chances to, you know, work, then it's more likely at LA or New York versus how many, you know, most of your actor's access or the gigs your agent will be sending you out for is like commercial work. And that's fine. You can make
probably a hefty annual salary just doing commercials, but then it's like, all right, I'm in Chicago and I'm just doing commercials. So it seems like you have this mindfulness or at least you're navigating a thought of like, I don't know how long I can stay here if one of your aspirations for achievement in this life, the fun growth and challenging journey of being a human is like, I might need to go to a place where I can.
deal with a little bit more volume of those opportunities and say, you know, Chicago.
Yes, I think there is a pressure inside me of eventually moving. Currently there's personal reasons as to why I'm still here. But yeah, yeah, yeah. I've been thinking about it for sure for a long, long time.
Mishu Hilmy (26:48.218)
What would be the signal like how like what do think the signal is to be like all right now now is the time to pack my bags or you haul and head west or head east?
Honestly, the big signal would be like if I made an IO house team or made like second city something for a year, then that would be the signal of like, okay, I can do this. Which sucks because I don't know why I put my own value with an institution's decision. But hey, I'm the apples. That's what I am thinking about.
Mm-hmm.
Mishu Hilmy (27:19.95)
Yeah, it's a construct, right? Like I think I relate, maybe I relate because I navigated a similar thing when I was doing a lot more stage work and theater work. So it's a good construct of this, this will be an indicator of growth versus like I need an institution to prove that I've grown. I need an institution to prove that I'm worthy. I need an institution. I need SNL. I need daddy. I need mommy to say like, you're a good kid, which there's nothing inherently wrong with that. But it's also like,
an external construct rather than what's the internal construct of like, I stopped performing because I stopped feeling nervous on stage. And like that was an internal construct rather than, I didn't get my shots or whatnot.
I hear ya, and that's good. That's like... I used to... and this is not you, but this is just like... There was this guy who I used to work with in the suburbs who he used to be a theatre person in the city and then he kind of left, took a corporate job and like...
He still does theater on the weekends, but like he has a kid now, he has like a wife. I used to think of that as like selling out and now I'm kind of think of it as like, actually seems nice. Like I love this work a lot right now and I don't think that's anytime soon, but I'm like, honestly, if I get to that life stage, I mean, sure, there might be some regret, but I don't think I'd be like beating myself up over it. I actually think I'm enjoying like doing that.
but I don't know. think it just, what I'm trying to say is I think that decision is something that was right for him in that moment. Actually, me shitting on it is very immature, obviously, but also, but also that's beautiful. And it's like, if I was ever there, you know, not going to, if I was ever lucky to be in that position, like, well, I think I would feel pretty good about it.
Mishu Hilmy (28:59.843)
Right.
Mishu Hilmy (29:12.876)
Right. Yeah. I think for me, it's like an annual practice of what is motivating me and what is enough. And if I didn't create that practice of at least consistently defining or redefining what the motivation is, then I might get stuck at like what
16 year old me she wanted. Yeah. And then I'm just like anxious all the time because you know, I'm not I'm not getting infinite blow jobs from strangers who work like, you know, that was what? Yeah, Yeah. Yeah. Yeah. Somebody vows. Yes. Yes. You know, so it's like, if I didn't have a sense of what was enough. And now I think also through like heavy reading about like psychology books, it's who is it? Martin Seligman's, I think, flourish.
my god. So many mouths.
Mishu Hilmy (30:01.442)
he refers to the acronym of PERMA. That's what kind of can help create like a happy life. Positive emotions, engagement, relationships, meaning and achievements. So it's like, all right, I practice gratitude. So my positive emotions are pretty consistent. have solid healthy relationships. So my relationships are consistent. Engagement, I have space to do creative work. My day job's okay, but if I'm not engaged with that, I'm engaged with this conversation with Ray. And then meaning.
you know, I believe meaning is your actions. So anything I'm doing is inherently meaningful because it's being done. So meaning is easy. And then achievement, that's, you know, the exploration. So how do I, how do I create constructs that like allow for that practice rather than external validators of, yeah, I, I got, I got on this or I got on that. But I just think it's like, it might be helpful to, at least I like to try to practice that of defining what's enough.
Yeah. Yeah, I think inherently that is like the fulfilling life idea and like, truly like, the idea of a sellout is really like you never took your shot. it's almost like-
Like, I think... You chose fear.
The true sad thing is just that if you weren't really in line with your values, but if you were like just going to the suburbs have a kid because you're like I actually want a family and live a little bit longer by earning more money. you know kudos to you. That's like yeah, that's not That's not anything like anything wrong with that Yeah, yeah I think as long as you're you're right as long as you're constantly checking out your motivations like if you move to the suburbs and you're like that was actually out of fear well then yeah, that is
Rey Tang (31:40.908)
you know, there's not much else to be said there. You just have to live authentically, which is...
Yeah, exactly. I think it takes courage to define the adventure that you want your life to be. And most of that adventure is out of your control. So what is control is like the perspective you have on when you're on the ride or on the adventure. So I found it for me, it's more easy to live with myself when I focus on the reason I love the entertainment industry or the creative industry is because I like I like people. like talking to, you know, smart, curious, passionate people like you, where we can catch up and, you know, get into the thick of it without the typical sort of
conventional or conformist fear of like, yeah, let's that weather. It's real nice. How about, how about them? How about that?
Were you the kid in high school that always liked a deep talk and never had
yeah, I was the cringe, cringe lore deep-
Rey Tang (32:27.01)
Ducks, probably smoking weed.
I was edged, man. was straight edged. Up until like college. Yeah, yeah, yeah, yeah. But that was, you know, probably just being sad or needing to be special. I need to be I need to be nonconformist. I'm yeah, I'm really grateful that we're kind of, you know, getting onto more of the sort of the sort of the emotional psychological elements. Like for me, it's people and process like I wouldn't be interested in
Well, me too.
Mishu Hilmy (32:57.176)
talking to you or doing this or being on set or writing, if I begrudged every email I had to send or like this hour we're on the phone or talking together was just dreadful, right? So I realized for me, those are the two core motivations that I have integrity with. I'm not really interested in impact and I'm not really interested in outcome, which are also perfectly valid motivators. I just learned over time, like I just don't, I could,
care less if my short film changes someone's life and they want to become a doctor because of it. I don't really care if my short film or my work makes me money or gets a bunch of laurels. Those don't motivate me, those drain me. But for some people that might be perfectly valid motivators. But that just takes that practice of tuning in on what you're excited about. And that always can change. It's like a magnitude thing.
I like my laurels, but I get it. I like changing people's lives. No, but I I think that's real. Figure out what you're looking for from your own perspective. Yeah, I never really thought about that. I'll give it more thought. Why does feel like I'm talking to my therapist? I'm always just like, you're so smart. I'll think about it.
Yeah, that's fine. And then I'm curious, what degree of risk taking do you inject into your creative aspects? Are you conscious of risk taking? I'm curious, what's your relationship with risk taking in any sort of creative endeavor?
Oh, I love risk taking. It makes me feel alive. Yeah, I'm always trying to do something different. I always there's this like quote. I don't remember where it's from. I think it be Monty Python, but it's like now for something completely different. Like, just like that idea. I don't know if that was a Python quote. But anyways, it's just like, yeah, it's just it's just like, I'm always trying to keep people on their toes. But um, yeah, like, yeah, I like being underestimated because then I can deliver.
Rey Tang (34:55.585)
Yeah, I really enjoy switching things up. Like recently I did a roast that was horrifying, very, very hard. One-liner jokes, which is not my strong suit as a comic. Yeah, I'm really putting down my own writing. I'm very proud of my comedic writing, but one-liners is its own thing. Yeah, they're very specific. It's a very hard and beautiful art form, but.
Mishu Hilmy (35:26.606)
exist anymore. yeah. And monologue jokes are typically like topical one liners or referential one liners versus I think maybe it's like the degree of self consciousness in terms of, you know, the cultural ebbs and flows of what genre of comedy people are tolerating. And I think we've been in a fairly decent period of like, either authenticity or self revelation rather than, you know, it's like, you know,
You got Mitch Hedberg, Steven Wright, Demetri Martin, and like that's where my reference levels of one-liner comics falls off. I'm sure there's some out there. I Neil Brennan had a one-liner section of his, one of his specials, but I don't, yeah, the kind of, those are like the three icons that I can think of, Mitch Hedberg and Steven Wright.
I forgot about Hedberg,
Yeah, yeah, that's a fun challenge. So how did that differ from your like typical writing process?
do like one liners. It was just a lot of like me writing set of premises and then a lot of figuring out how to twist it. It became very formulaic in a way that really tickled my brain. Like I was really deep into it. I was losing sleep over it because I was so... Valentine's Day, did not really... I was with my girlfriend, but I was not thinking about her all the time. was thinking about this white boy who I had to roast. It was really, really quite romantic for me and him, not for me and my girlfriend.
Mishu Hilmy (36:34.593)
yes.
Rey Tang (36:50.606)
It was very hard, but I love joke writing. So honestly, it was a really nice, that's what I was addicted to. I'm not in it to like make fun of people or punch down. Like I'm in it for the joke writing part. that's what makes an audience laugh. What is the science behind it? That's what's fascinating me. And still is, you know, fascinating to me in normal standup as well.
Right. the logic and mathematics of like, just a structurally sound joke are are are delightful. They take all that that brain that challenge that sort of proof element. And how can you surprise and like vary, you know, variations?
obsessed with it. I think it's what, It's very funny because I talk a lot with Tuxford. Are you interviewing Tuxford?
I gotta reach out to them. Yeah
God, that would be great. But Tux is very, very instinctual, like emotional, like their funny is just coming from them. Like it's just not, it's not my funny in that like, it's like, I think they're very funny, but I, it's just, approach comedy very differently. I always tell them, I'm like, you're the antithesis of everything I represent. I'm like, you can like, there's no such thing as natural talent and like, well, Tux or just oozes natural talent. It really.
Rey Tang (38:02.794)
Not to say they don't work hard, but it's just... They got talent, baby.
Right. remember when it came to like comedy, one of my favorite teachers who was at UCB, I think he's still in New York City doing work, Michael Delaney, he would say, you know, there's sort of two polarities. yeah, two sort of two polarities of comedy. There's, know, the funny bones and pitch perfect and then just mere mortals. Right. So you got funny bones. You got people like, you know.
Chris Farley, Will Ferrell, and Kristen Wiig. There's something about their being, their presence that's just funny. And then Pitch Perfect, you got some like Zach Woods and also Kristen Wiig. She's like, know, just turns a phrase that's comedically pitch perfect. Not that they didn't like work at it, but yeah, it's hard. It's hard when you just have like a certain energy or a certain tempo that's just like funny.
Yeah, it's what I don't have, which I've... Well, no, don't have it the same way Tuxword does. And so it's very interesting. But you know, I believe that anyone can be funny. And also, I love categories because they're in comedy because they're so... At the end of the day, we're trying to make something science that's not science. What is so funny about it is like...
I agree, yeah.
Mishu Hilmy (39:17.74)
Yeah
I'm futilely trying to figure it out, but on the end of the day, I come up with seven jokes that I like, carefully concocted, and it's the fart joke that works. Like, there's no obviousness with any of it, which is-
Right. And also like it's hard to experiment because it's like that was the one audience that night. The reference level of that audience, like you can't control for it. So you can structurally try and make sure it's like a drum tight joke. used to try and write like 10 one liners a day. I did it for maybe like a year and a half or two years. And it was just like that thing of brainstorming themes and trying to turn them. But it's I would I would like sometimes go to sleep and wake up.
with like a fully formed joke. It might not have been the best joke, but I just like woke up in middle of the night. Here's a one-liner.
Yeah, your brain's in it and that's a good place to be.
Mishu Hilmy (40:05.996)
And then your normal standup, like, do you have a writing routine or consistency? Like, what's, you know, what's your sort of genre right now? How are you approaching it? What are you kind of revealing, not revealing, you know, how's that process?
I do naturally tend to go towards storytelling. It's naturally more like, instead of doing like a true storyteller, like I'm no Alex Edelman in how he purchases it. I think it's more, I'm more like find the jokes of it and then hit those. no matter how jagged the path is, find the funny of it and then just hit those beats. And let's see. I've been told a lot of my comedy is more shocky, which I don't.
I'm not trying to do and I'm actually trying to move away from it a little because it's not, it's actually not very close to my style at all. Yeah, I'm not trying to be an edgelord. I really don't want to be. I just, I'm just trying to find the thing that makes you laugh. Yeah, I would say it's like personal jokes that naturally have, tinge into political because, yeah, because of who I am.
Right.
Mishu Hilmy (41:11.829)
Yeah.
Rey Tang (41:16.024)
But yeah, it's been fun. I think I'm more like of the current stand-up. It's not the one-liners, but more of like the, this is a funny premise, let's explore that for a bit.
You're not necessarily doing a full story, right? You're not building a five minute chunk to a 10 minute chunk to a 30 minute storytelling piece, but rather you might let the story kind of be the baseline of like, here's 90 seconds that I can extract as many laughs from this bit before I just turn to a sort of revelatory or a story chunk there, right?
I'm very much about just finding the laugh and leaving. I'd like to get to a point where I can sit in a serious moment, but you can't do that in a 10 minute set.
Yeah, it's hard when you got like, yeah, four minute, 10 minutes set. And when it comes to say like, writing, like, how, how have you gone about going, you know, rotating new works and you know, like, what's, what's your generation approach of thematic kind of elements? how are you just generating go, oh, this is what I want to talk about this week or this month.
I have a list. No, I know what you're asking. I don't have a discipline to practice. I do try to write every day. It's sort of like hit or miss on when I do it. It's either my lunch break or right before a show or typically after work or lunch break is my like peak hours. I don't really, I used to do it at work, but I actually like my job right now. So I am not doing it at work.
Rey Tang (42:49.582)
yeah, it really depends on the moment. I really try to take advantage of my lunch breaks. That's mostly when I start to write. I also take advantage of train rides. That's where do a lot of I'm obsessed with it. I was practicing a Russian accent in public on the CTA and that was weird. people were confused. Well, you try, you know. Yeah. yeah. And, yeah, working hard.
Yeah, great.
Rey Tang (43:19.756)
Yeah, and it's never coming from a... I don't know, I always try to... I'm never really telling the truth on stage, is what I think. I don't think any stand-up should be fully telling the truth. I think that's weird and...
It's like therapy. Tell your doctors and your rabbi.
We're here to make it funny. But like if it's a very weird truth, like you should, you should be honest. I think there's a line obviously, like I'm not going to say I got hate-crimed just for fun, but like, like, yeah.
yeah.
Yeah, think, you know, truth and comedy is probably one of the worst, worst buzzwords that Sharma of all. agree.
Rey Tang (44:01.478)
I hate you, I think that's stupid! Ruth, I'm telling you what you want to hear to make you laugh!
Also like truth is too abstract when you're improvising or where you're on the stage like It's too. It's just too philosophical versus at the improvisational level. It's like I think you're more you're you're you'll have a stronger scene or entry if You think recognition like in this moment? What's recognizable? Right, what's the truth of this moment? Like that's right. I'm gonna taxi. Okay
Oh, yeah, you know what I hate in taxis is that screen that has all the ads. So, okay, I'm just gonna start the scene where I'm like trying to turn off that fucking taxi, taxi TV. So just think more of recognition. And so I think standup is probably also similar of like, how can you create recognition? But that's also the beauty of standup. Like you have the idea and you don't know if an audience will relate to it. So then you go and like, oh no, this is not.
universal experience that people can connect with. I better just let this premise die.
Yeah, I got a couple of those. I had one about poly people. It was a joke about how poly people are the most boring people I've ever met. Just like the idea like everyone thinks they're very wild, but actually they just want to play D &D.
Mishu Hilmy (45:26.154)
Yeah, yeah, yeah. But, was too... Tunish, tunish.
It was Duneesh. Like I can't play that to McHenry, Illinois, you know?
Yeah, yeah. And then I'm curious, like when it came to you mentioned earlier, the sort of the feedback you got from friends or people who have seen your sets that they're like, you're you're a little bit, you know, maybe you're either not necessarily agility, but darker or raunchier or whatever the kind of descriptors they had. when you get that kind of feedback, like how how do you integrate that or shift and go, well, I don't want to be known for being sort of
to in your face or whatever it is, like how have you been navigating that type of feedback?
something my mom used to tell me when I was really like just starting and screenwriting again there's just a period of time where you're gonna suck at it and it's right part of the process yeah but my sucking at it was I was a high schooler and I was writing about death and like marriage like very like life-altering events and my mom told me when you get older actually the things that interest you aren't the big things and so I think with comedy it's something similar is what I'm realizing
Mishu Hilmy (46:25.09)
Yeah.
Rey Tang (46:36.236)
And that the shocking thing is what makes you think is funny and makes you laugh when you start off. But eventually, the best bits in my head are not the shocking ones. The best bits are like, what's up, pussycat? At the diner that Malaney does. They're the smaller ones. They're what life is. So I think it's just time. I'm going give it some time to be like, when I mature a little more as a performer, I'll be able to mine smaller things.
I think I
Mishu Hilmy (47:05.836)
Right. Totally. Yeah, think I, gosh, I don't remember this teacher at Second City. I know his name was Norm, but I can't forget his last name. I think he referenced- McDonald's? Wow. Norm MacDonald. Yeah, yeah. Norm Norm Holly, yeah. I think he mentioned like, that's either him or Michael Gellman. Maybe they both had this similar phraseology, but that's a blood in your, blood in the mouth joke. You just like hit the audience with a punch line that's like.
so shocking or so surprising, you will get a reaction. Some people might laugh because they're uncomfortable. Some people might laugh because they're shocked. And some people might laugh because they don't know what to do. But what you've just done is now for the rest of the show or your set, they're dealing with blood in their mouth, right? Like that's kind of like what the tempo or tenor you set up for the audience. And like, how do you become more mindful of like, am I wittingly or unwittingly just doing shock punchlines or blood in your mouth punchlines versus
what's something that's a little bit different than my default. And then I also remember, I think George Wentz, who was a Second City alumni, he was on Cheers, he played Norm, but he did a at the Chicago Humanities Fest. And someone asked him about Second City during the Q &A, and he said, you know, I was on Mainstage for, don't know, like two, three years. And what he learned from his time on Mainstage was he would do the same show, the same sketch show over and over and over again.
And what got the biggest, richest laughs were not how big or broadly he could play the moment, but how much smaller and smaller and specific and subtle he could be. And I think that applies to almost every art form. You know, when you're first starting out, you want maybe those broad, shocking punk rock edge lord strokes. But I just thought it was interesting. Like, wow. Yeah. He got to iterate. He got to practice.
What a playground, what an experimental zone, a testing ground for him and probably others. You're up there, know, twice a night and you get to realize, shoot, it's actually when I become more specific and smaller that I can destroy the audience.
Rey Tang (49:12.217)
I like that. That's a fun tip.
Are there things that, so you got this podcast, anything else that's kind of on your mind creatively that you've been thinking about, hung up on?
I'm so I'm 25. 25 is the age when you realize the people who are ahead of you are younger than you. And it is the oddest feeling in the world. Because on one hand, my therapist, therapist brain knows it's like, yeah, age doesn't matter. You know, they've done this longer. They've cared about comedy, maybe forever. Or maybe they didn't. And they're just a star, you know, like none of that.
really matters to you. But on the other hand, it's hard to see somebody who's younger than you. It's weird. don't know, I know it's just, know, mathematically it's just gonna keep being this way, but it's weird. It's a really weird feeling.
Right, I guess I'm curious, I understand I relate to the thought, we've all been there, but what value, do you have a belief system that says the age of success matters? Yeah.
Rey Tang (50:20.902)
yeah. yeah. Am I not supposed to say that?
That's fine. It's fine. But it's like, it's like, and is that belief system? Like, is that valuable to you? that has that been helpful?
No, no, no, no, it's not a good thing. But you asked, do I hold that value? The first thing I do when I, this is the sick thing. The first thing I do when I find out if somebody's famous is I Wikipedia them immediately. Like I was like, okay, I got a few years or okay, losing time. deeply sick things I do.
Yeah, yeah, yeah.
Mishu Hilmy (51:00.558)
I relate to because it's I think I peg it to what I would call for myself, my behavior, the formalist or the institutionalists mind view of like, I need to get as much information to create a narrow path, right? Okay, this person, they were 28 when they got on SNL or this person, they were 32 when they got, you know, got their second Sundance feature or whatever. And it's like, I'm trying to capture all this information just like, tell myself I'm on the right path. But
Ultimately, it's it's sort of a boring path where if I'm like, got to follow exactly the way what Adam McKay did, or I got to follow exactly what Tina Fey did or whatever. But at least that's what my my impulse to do it was to create sort of, you know, waymarkers, a roadmap to say this is the journey I should have rather than like, OK, Charlie Chaplin and Buster Keaton innovated cinema before I even existed like and also the
industry will never be as structurally sound as it was from 1920 to 1948. So like, why am I so hung up that this 22 year old just got a palm door or whatever?
Yeah, yeah, yeah. It's a really odd experience. And it's just like...
it's, mean, so listen, at the end of the day, I'm well adjusted enough to be like, I know this is wrong. And I know like, you know, like I'm aware, I'm well aware that like actually thinking this way can only lead to ruin. And like, I, what you're saying about forming the roadmap is relatable, but, yeah, it's, it is, there is something though. I think it's just the first time I've really experienced it. It's like,
Rey Tang (52:47.566)
Oh my gosh, these people are coming straight out of college and doing amazing things. That is like a very odd, because you know, I, not to toot my own horn, but I'm very happy with how my career has gone. I feel like I've done a lot of cool things, but I just, man, it's hard not to be, for lack of a word, mentally ill. Like, you know, like not have a skewed word, but a skewed worldview, you know?
Right. Yeah. I think it's just being aware of the defaults, right? Like being aware of those impulsive viewpoints. And I wouldn't even peg it as wrong. I would just kind of go like, well, what is this motivating, right? To be really focused on folks' age or a cohort or a generation or two behind me. All right, I'm paying attention to this. Well, what's this trying to inspire? The most optimistic viewpoint is, it's inspiring movement, right? Maybe it's me telling myself I want to take different risks or I want to try different mediums I want to
be more consistent or perform more consistently versus like this is a wrong viewpoint. However, a sustained viewpoint like that maybe not lead to ruin, but might lead to motivating behavior that's mean to yourself and out of your control, right? Someone being 20, crushing it is really out of your control rather than like, what is in my control? Did I write today? Did I think about an idea? Did I do that?
But I I feel that I think it's, it's, I think it's a fear base to have as the door closed, or as the window closing, or as the window now shifted three miles to the west, and I got to like run all the way over there. So it's fear, because we talked about opportunity, right? LA, New York, or whatever. I think there's an element of fear of has has the ship passed? Am I
no longer in vogue? Am I old news or whatever kind of thoughts? Am I irrelevant? Going going back to that thing of being special. But really, that's answer. Yeah, yeah.
Rey Tang (54:48.75)
We're irrelevant now.
There's also, there's like, I'm irrelevant, but you're not irrelevant to the people that matter to you, but.
I think that's real. think, yeah, yeah, that's another really good way looking at it too.
Yeah.
If I ever get too heady about all this, I just think there are people that love me and I'm going to go hang out with those people now, actually. Even if I hate myself a little bit, there are people that love me and I'm going to hang out with those people. Like, at some point. Yeah.
Mishu Hilmy (55:10.839)
Yeah.
Mishu Hilmy (55:16.778)
Mm-hmm. ahead.
Well, just sometimes you lose sight of yourself. So it's nice to be with people who can.
Totally. And that's why I think like, you know, when I do think of that idea of perma, it's like, well, accomplishment achievement is something that gives a fully fleshed human experience, human life, just as much as relationships, just as much as meaning, just as much as engagement, just as much as positive emotions. So I need to not judge that part of me that also values accomplishment and the challenge of it. And at the same time, how do I define my relationship to the way I approach those challenges, you know, versus when I was 20 and compulsive and
I couldn't eat a dinner without thinking of what would be a good improv exercise. What would be a funny improv team name? would be, how do I get on this person's radar? Like, man, I wasn't not thinking about comedy. would wake up thinking about writing or comedy and it pervaded.
I get that. But yes, it seems like something you figure out eventually.
Mishu Hilmy (56:17.752)
Well, yeah, I'm glad to hear it. I'm here to chat about it anytime. Ray, it's been a delight. Thank you for sharing your time, and I look forward to the next time we talk and hang out.
Thanks for having me.
Mishu Hilmy (56:37.518)
Before sending you off with a little creative prompt, I just wanted to say thank you for listening to Mischief and Mastery. If you enjoyed this show, please rate it and leave a review on iTunes or wherever you listen to podcasts. Your support does mean a lot. Until next time, keep taking care of yourself, your lightness, curiosity, and sense of play. And now for a little mischief motivation. All right, here's a little mischief prompt. Hope you do it. I used to do this actually a lot every day for a few years.
where I would set a timer for 10 minutes and write as many one-liner jokes as possible, choosing to aim for quantity over quality, trying not to edit. So no edits allowed until the timer ends. I think this taps into divergent thinking as well as quantity over quality ideation, which, I don't know, research shows that it can help destroy or take down perfectionism and just increase originality. So divergent thinking, just throwing out as many ideas as possible without judging them.
getting quantity first so maybe you can find an unexpected gem later and that could be years later. So that's a little mischief prompt. Hope you enjoy. Get out there, do some joke writing.