Thinking about Class with Madison Shepard

INJ 83 | Life And Comedy


Madison Shepard is a stand-up, writer, and actor. She’s appeared on Comedy Central’s The New Negroes. She’s performed at The S.F. Sketch Fest, Broke LA, and Laugh Riot Grrrl Festival. She studied acting at Los Angeles County High School for the Arts and The Royal Central School of Speech & Drama, in London. Madison is soon to release her debut EP “Goodnight Silverlake.”

Listen to Episode #83 here

Thinking about Class with Madison Shepard

Our guest is Madison Shepard. Madison is a stand-up writer and actor. She’s appeared on Comedy Central’s The New Negroes. She has performed at SF Sketchfest, Broke LA, Laugh Riot, Girl Festival and she studied acting at Los Angeles County High School for the Arts and the Royal Central School of Speech and Drama in London evidently that cost a lot of money. Madison is soon to release her debut EP, Goodnight Silverlake. Welcome, Madison.

Thank you.

Madison, if you weren’t working, I know you don’t know this question because you didn’t know the name of the podcast.

I didn’t, I’m sorry. Danielle Perez and I have been friends for years, she recommended you. We’ve been best friends for years.

She recommended you and I was like, “Yes.” We’re even.

We’re great.

If you weren’t working as a stand-up, writer or actor, what would you be doing?

That’s something that I think about a lot because I’m like, “At what point do I throw in the towel?” I’m not there yet but if I bomb tonight, I may be like, “Maybe, I should go to school.” The thought did pass my mind that maybe I would be a massage therapist because I hate school and it’s a short amount of studying to become one and you can make your own schedule.

Would you be one of these massage therapists who talk to their clients?

No, but maybe happy endings, that seems to be where the money is anyway, like rub and tug maybe, I don’t know. I’ll come to you or you’ll come to me. Can we talk about that?

This show has an explicit rating. You’re safe, people have said much worse. Are you performing? What are you doing?

They have a comedy show at the Kibitz Room.

Are you doing a Nicole Blaine show? Nicole was a prior guest. Would you give her my best?

I will, with pleasure.

We’ll get back to your massage therapy, legal or not. Have you done the Kibitz Room before?

I’ve never done it before but I’m excited to do it.

Are you doing new material? Are you doing strong material?

I just did an EP of twenty minutes. It’s two showcase sets, the two that I do in Los Angeles. I am doing one chunk that is on that album and then stuff that I was working on prior to putting that setlist together for the album, it’s newer. I’m the type of person who will sit on material for a while and run the fuck out of it. There is newer material in the sense that it was written in the last months.

I only ask that because the particular night I was there, which I couldn’t tell you if it was a regular night or not, a fairly set of accomplished comedians come through.

Cameron Esposito is on this one.

I felt like they were doing a lot of new stuff, some people are doing some half-baked ideas.

I love the workout room.

The problem was the audience wasn’t picking up what they were putting down.

That could be a problem.

It was funny because comedian after comedian came up and faltered and then turned the room against them by complaining about the audience. That happens in LA more than in other places but it was fascinating. I wish I could remember the gentleman’s name who finished. He’s a comic from Memphis. He was great, he comes up there and crushes it and it was such an interesting experience, everybody was like, “What is wrong with all this stuff?” This dude then gets up, all shocks, and told a story about a porcupine living in his house and killed. It didn’t help me sitting in the front with my arms crossed, analyzing jokes as a scientist.

I oftentimes feel that people will shit on the audience and we also have to take. I always think it’s three or four things. It’s me, it’s something in my timing, my timing might be off, my delivery might be off, my energy might be off whatever. For the room, it might be too big, too little, too slow, it could be the audience. That is a fact they do not like what you’re doing or they might be sick of sitting in traffic, whatever. It could also be the venue and it could also be the luck of the draw. It could be anything.

When you point these out it reminds me of how people say to me, “You can’t study comedy. You can’t dissect it if you didn’t understand it.” Because if you’re a comic you feel these whims, a shift in the wind and suddenly the laughs evaporate, as a result it feels you’re a lot more ephemeral, a bit more magical, uncertain, random and so on. My response is that science is good at filtering out systematic, random and finding a signal in the noise in order to answer any questions.

There is a magic in performance, in general, because the nature of it is to channel something otherworldly and then to bring that through yourself and put it out into the world. There is something there that we can’t quite explain but jokes are mathematical and timing is mathematical. You can say anything, it could be a plain sentence but if you time it correctly, you make a joke out of it. It’s comics trying to big themselves to be like, “It’s the magic, you can’t study it.” You probably can and people should. Stand-up is relatively new, it’s an art form. Why not study it?

I will die on this hill but I don’t want to. Maybe you can convince me otherwise. They’re critiquing the audience for not laughing is in any way a good strategy?

It’s like when you’re fucking someone and you’re like, “Why aren’t you coming?” It’s like, “What are you doing to engender that?” You can’t shout at somebody to come, you have to figure out a different way.

Madison, don’t quit being a stand-up. I don’t think I would come up with that analogy in part because as a professor I probably can’t go that off-color. Secondly, I don’t think I could come up with that analogy that quickly in order for the comic effect of that all. I was doing a bit of research on you, admittedly not enough but you made a comment on one of your videos about being raised by a white mom in the hood. Tell me about your white mom in your hood? What’s the story?

My mom is a nice lady. She’s not with us which is a joking remark, was like, “She’s not with us but don’t worry, she’s not dead, we could talk about her.” She’ll probably read this. She loves me and is incredibly supportive. My parents met doing a show, doing theater in Dallas. When they got together, they dated on and off and I came along. My dad was not prepared to be a parent and was super not around. My mom with a degree in theater and a half-black child had to make some choices living in Dallas, Texas which is still a segregated, racist place like there are places that she couldn’t have my baby picture on her desk. She could lose her job because she has a black child. The race is a big issue.

They’re still in whatever. She raised me in the hood in Oak Cliff. We didn’t know this at the time but was slowly starting to gentrify and it’s gentrified now but the roots and seeds for that were planted in the ‘80s and ’90s when I was a kid there. A lot of artists like my mom and a lot of queer people move there and slowly, it’s more she-she than it was when I lived there. You couldn’t get a cab to take you from the airport to Oak Cliff back in the day, it’s an expensive fare. They were like, “It’s late at night, I’m not going to the hood.” She raised me there by herself and my life was always these dualities. I lived in the hood but my grandmother lived in a trailer on her sister’s cattle ranch. I spent a lot of time being in the hood but I spent a lot of time herding cows, fishing, shooting guns and skinning the animals.

You have a red-blue dichotomy.

I took ballet, growing up I played the violin, I always did theater. My life has always been this way where it’s like both this and that. I’ve always been a little of this, a little of that my whole life. Growing up with a white mom, at the time when we moved there, it was a black neighborhood but by the time we left, the majority was Latino. That was also an interesting moment in my life in terms of racial identity and how I identified, where I fit in with this society that I was living in. I haven’t even cracked the shell of the crème brûlée of that, there’s so much there. I’ll probably write a book about it or something.

Do you have jokes about this?

I have probably fifteen minutes on my mom and growing up in Texas.

Most people don’t grow up in a place that changes while they’re there. I had the same thing, the reverse of sorts of the white neighborhood that experienced white flight and by the time I left was mostly black. As a white kid it was a good experience because the average white person doesn’t have that much exposure to people who are different. It’s like segregation and eye-opening, empathy-causing.

It also makes people realize that we’re all the same in a way like not to paint it with that brush, I realized that cultural and socio-economic and racial things do exist. However, as somebody who experienced that, I can tell you that I’m not mystified by Latino people because I grew up around Latino people. It left an imprint on me that was strong and I feel it has made my life better. It’s made my life more beautiful and enriched having grown up with people who are not exactly like me.

This gets discussed mostly when it comes to gender is that we tend to focus on differences, how men and women are different, for example. If you were to plot whatever the things that you measure in terms of differences, you see two bell-shaped curves with some people far on one side, far on the other side. Most people in the middle and yes there’s a gap between the means of those two things but there’s more overlap between the two than there are, mainly, because we’re living in the same world with similar types of problems. That said, culture, gender orientation, socio-economic status, etc., moderates a lot of these kinds of things.

This duality idea is an interesting one. When you start looking for it in comedy, you find it a lot in the sense that you find people who don’t quite fit in. They don’t fit in for a variety of reasons. Sometimes they don’t fit in because they don’t like to play by the rules. Another way they don’t fit in is because it’s a common comedy trope, fish out of water. Freaky Friday, let’s just make the daughter the mom and the mom the daughter and comedy ensues in that sense. You were living. I don’t want to say that your life is a comedy trope but trading places. It goes on, you can find this everywhere and the kid who’s fishing and hunting on the weekends and hanging on in this gentrifying neighborhood on the weekdays and vice-versa.

I would say that’s definitely true. A lot of comics are outsiders and in some way that’s how you get to have the overview which is good and bad. It’s hard sometimes when you have to have a strong POV on something. For me, I’m mixed. I’m black and I’m white but I’ve been with my rich cousins and I’ve been at the trailer and I’ve lived without electricity. I’ve seen the helicopters put the light in my window because they’re looking for somebody who’s jumping fences because they robbed a bank or whatever the fuck is out. Wild shit, that’s a common thing in comics. That and having a home where it’s one parent or divorced parents or two parents in the home but one is completely absent emotionally, spiritually, intellectually or whatever. That’s something that we all share.

It’s this idea of perspective-changing, comics don’t create laughs without being provocative. Having a different perspective that they can make in some way okay or they have the same perspective but they find a way to make it a bit agonizing. I get a kick out of watching comics who do this, everybody thinks X, I’m going to say Y and I’m smart enough and I’m likable enough. I’m everything enough to create laughs out of this thing, is that first blush? It’s not the right thing to be saying, not a normal thing to be saying, not to a normal perspective. Do you have a particular joke that feels like that? You’re essentially making an argument for something that the average person in the audience at first blush wouldn’t agree with.

To change somebody’s mind?

My guess is probably to get a laugh first.

I love misdirects. I have a joke that is going to be on the EP that is about new metal and how much I loved new metal as a preteen. I’d go through all the examples of why I loved it and who I was at the time.

You’re going to have to help this guy, I know heavy metal.

New metal happened in ‘95, ‘96 when Korn released their debut album.

I was heading into grad school, those years are a cultural blur for me.

It’s heavy metal and hip-hop together, it’s Korn, Limp Bizkit, Linkin Park, System Of A Down, Slipknot and all these bands.

I didn’t know what they were but I know those guys. I didn’t mean to interrupt, so that’s new metal?

[bctt tweet=”No one can take your Emmy bid seriously if you’ve never had to pay your own rent.” via=”no”]

I like to say things that are shocking but also true, you didn’t think I was going to go there like, “I used to cut the crotches out of pantyhose and wear it as a shirt and all this other stuff.” It’s hard to explain it but I’ll try it but the punch of it is I was angry and opinionated for somebody who hadn’t been raped yet. It’s true and accurate and probably true of a lot of women in the audience and men too. I don’t know if that’s what you’re asking for but I like that stuff. For me, I’m saying something true and it happens and it’s like a little flash of boom.

I had it when you said that.

I love a misdirect. I try to do them more. I’m trying to think of more. I had this joke about my ex-boyfriend blocked me on social media which is hard because how can I ask him to move out of my apartment, probably my favorite one. It’s quicker, it didn’t bring up rape but there you go.

That’s a fun one.

I like that stuff.

That seems like the kind of joke that you can build out in a bunch of different ways.

I did, I like that because it’s great, it’s an in. It’s a breakup joke, it’s letting you know this man still lives at my house, the next beat of that is I love True Crime but it’s a problem because I have this man sleeping on my couch. I keep thinking I’m going to see him stand over me with a knife and watch him still do not have enough commitment to take my life. It goes on like that. That was a lot of fun and painful too.

Was there a kernel of truth to that story about him not moving out and the blocking?

All of it, he lived with me. I was nervous and I love True Crime. He did want to commit to me that was a problem. That was the only part that was a lie about that.

The idea that people talk a lot about truth in comedy and the issue is like, “That’s half right.” The issue when people say, “It’s funny because it’s true.” It’s not the right way to think about truthfulness in comedy, the way to think about it is with regard to authenticity in comedy. That is the things that you don’t want to talk about are the things that are often funny, a truthful story of going to 7-Eleven and buying a pack of cigarettes is not funny even though it you could be perfectly accurate with it. It’s the thing that happened and it is real that you go, “I don’t want to talk about that.” That’s the thing that often makes good comedy fodder. The things that are embarrassing. The things that are painful. We’re going to pass on this massage therapist stuff. I hope you don’t give up comedy quite yet. The woman from Texas went to High School for the Arts here in Los Angeles, following in her family’s lineage of artists, it sounds to me that you had that artistic streak rather early in life exposed to ideas.

My mom was a playwright, I was at every rehearsal. I was at every read-through. I was at openings, closings. I was around a lot of theatre and theatre-makers growing up. I don’t think I had a choice but to turn into an artist myself. Maybe I could have but I don’t think that’s how I was groomed. I was groomed into being one as well, which is fine.

You have one life. You might as well do something interesting with it.

I suppose. I could use it with some more money though.

I was having this conversation. I have a bit of a love affair with Los Angeles and one of the things that I like about this city and other cities like it, the one coming to mind is Dubai. I spent some time in Dubai teaching there and I’d like the same thing about those places, it’s a place that people go to pursue their dreams, as imperfect as those dreams may be. The person I was discussing it with, she said, “I think it’s sad all these people coming here and failing.” The answer is, “Of course, that’s unfortunate.” Plenty of them fail because it’s a big funnel and a few spots, but I credit folks for that type of optimism, that type of risk. Belief in yourself, giving yourself a chance as imperfect as the context in this situation may be. Sometimes given how overmatched some people are that they may be unskilled and unaware but yet that optimism, I find it uplifting, I find it inspiring.

It’s beautiful and it’s also tragic in some ways. Hollywood is filled with stories of people killing themselves over their clippings. Killing themselves off of the Hollywood sign. There’s something that’s hard about it and is grading and grinding but if you can stick it out then it’s not so bad.

We were talking about a comic before, who I’ve known for a long time. I knew him when he had a car then I knew him when he didn’t have a car and I knew when he had a car again and now has a TV show. There are ups and downs and that kind of stuff. You went to an arts high school. My only experience with arts high school is the television show of Fame. Is the portrayal of arts high school in Fame, this is maybe before your time, is it accurate?

There are parts of it that are.

INJ 83 | Life And Comedy
Life And Comedy: Hollywood is beautiful and tragic.


Is Glee an arts high school?

No, they’re just a regular high school. I found arts high was hard because it was the first time I was around that many white people. Also coming from Texas and I moved to Los Angeles on September 4th 2001 and my mom hadn’t moved here yet. Within a week 9/11 happens and the nation goes crazy, it was a weird time for sure to be a kid. My school is good. A lot of the teachers who taught there also taught at different universities all over Los Angeles, USC, UCLA, CSUN, all of that so my days were broken up with four hours of academics and four to six hours of arts training every day for four years. By the time I left, I had a college-level actors training. I did the Suzuki method which is a lot of stomping and whatever. I’d done a lot of voice training. I was trained in Shakespeare, Chekhov, commedia dell’arte and all these things. It was enriching. I also took as little academic classes as I could get away with. I took a lot of film classes and TV classes. I won an Edinburgh scholarship while I was there for TV production, I thrived. I hate school but I did like arts education. I loved it. It was hard and challenging and unfair a lot.

Why so?

There were class issues. We were living in hotels, my mom and me until I was a junior. At the end of the junior year, we got our first permanent address in Los Angeles but before that we were living in roach motels all over the city having to move around a lot. There were times when I was the only person employed in the household. I was a high school student and working part-time. That was tricky often and the highlight of my weekend was eating moon pies or some dumb shit, then I’d be sitting next to somebody who’s like, “We took my boyfriend’s helicopter out.” It was hard in that way and this is still true for artists. If you do not have to worry about the day-to-day problems of like, “Where am I going to sleep? Where am I going to eat? Where am I going to bathe? Do I have enough money to support myself?” If you are financially stable, you don’t have these added pressures on you right and that takes away time from creating art, from getting better, from getting stronger in your chosen field. I felt a lot of the kids who were better-off and frankly well-connected in the industry, some of them were at the Emmys. Those kids had a different career trajectory than someone like me, I’m not coming from a deficit but I’m coming from a lower place. Financially, I felt it was a huge struggle in my training and class is still a big issue for me.

When you said unfair, I wasn’t sure where it was originating from but I completely agree.

As a kid you don’t understand this. As an adult, I still don’t.

To reflect back, what you’re saying is we have a tendency to romanticize the struggle of our sport, science, business, etc. When you take a good hard look at it, it’s the lack of constraints that are more beneficial than the presence of constraints, generally the case. If you’re well-rested, if you’re well-nourished, if you’re healthy, if you’re free of worry and anxiety that leads to more creativity than the opposite. I forget where I saw this and I can’t remember if it was about professional sports but if it was basketball or football. We have this tendency to think about football players coming from underprivileged backgrounds because most football players are black and in the professional ranks especially. However, someone did an analysis and finds a surprising amount of them come from more middle-class families. You start to unpack that and you go, “Why would that be the case?” “Middle-class families have more resources.” You can dedicate more time to the sport because you don’t have to get a job.

You can hang out after school.

A game that is built on being highly physical and athletic, you benefit from eating better and having better coaching, facilities and all these kinds of things. If it’s present there I don’t see why it wouldn’t be present in the arts. The second one which you’re absolutely right about is the role of parents. I’m getting old enough where I’m starting to see the kids of famous people in the arts and entertainment. They may not always be as good as the parent but they’re there. It’s like the parent is able to open doors for them, make introductions, the brand name and then also the parent is there to cut a learning curve. Plus, the resources that these wealthy parents have, better training or opportunity, you don’t have to go bag groceries down at the supermarket.

I tweeted this rather saltily but I can’t take your Emmy bid seriously if you’ve never had to pay your own rent. If mom and dad have always paid your rent and you’ve never had to worry out the 27th of the month like, “Am I going to do it? Do I have to choose between gas and food?” I can’t relate but maybe that’s just me.

This is an interesting question, how much should the art be judged by the advantages or disadvantages of artists? We do have a tendency to enjoy the stories associated. On my Twitter feed, whenever a famous person’s name pops up, I’m always worried they’re dead but sometimes it’s just their birthday. It was Bruce Springsteen’s birthday, he did not die. He’s 70 and he’s strong like a horse or an ox. In any case, that’s a guy who came from pain, it’s a nice story, his music coming from pain, that enhances the story associated with it but no one gives a shit that his music came from pain if his music is not good. I’m curious about that. It’s a nice added element to watching or listening.

It’s about showing your work on the mathematical equation. What was your process? If your process didn’t involve sweating it a bit, for me as an artist and also somebody who consumes, I care a little bit less. Your career milestones mean a bit less. I know that for every one of you there are thousands of people who are better than you or are good. Because they didn’t have those same opportunities aren’t in your position. I also think that it’s the nature or the thing, sure we’re all individuals but at least in the industry we can rotate a new one. There’s a quote from To Wong Foo, Thanks for Everything! Julie Newmar. It’s about sex but anytime one of the lights goes out on Broadway you can just unscrew the light bulb and screw a new one back in. It’s like that in a way but that’s me, I’m focused on class.

Given your background, that clearly makes good sense and obviously it’s finding its way into your work.

I should say I have a lot of shame and weird feelings about being poor and having to lie about that. Covering up that and I’m exhausted by that. It felt like it warped my experience as a person growing up in the world. I’m starting to talk about the actual nitty-gritty facts of it a bit more, that’s also why it’s at the forefront of my mind.

I’m glad you’re doing it. As if Los Angeles County High School for the Arts wasn’t enough, you went to London and studied the Royal Central School of Speech and Drama. Tell me why. Did this have a magnifying effect? London is one of those places that’s an expensive great international city, diverse but also one that’s class-focused. Tell me a little bit about that.

After high school, I didn’t get my first speaking role until my senior year. I was in the choruses for every show. We did four or five productions a year. Even though I would get callbacks for all the leads, I would be given no opportunity. I don’t know how much race and how much people’s parents are donating time and resources to the school. I don’t know what the equation was but it certainly wasn’t talent. That soured me on theater, acting. I didn’t see a way for me to get ahead or even have an opportunity. Also during this time, we have a lot of body positivity now but there was not that then. I was a size ten, a size eight and being told that I was too fat to act, to tell stories. It was all a fucked-up time in my life.

After high school, I got a job. I didn’t go into college until I was 22 and I said, “I had quit the theater.” I slowly started getting back into doing theater doing some stage managing. I did a lot of work with Shakespeare in the Park here in Los Angeles and slowly tiptoeing. I was like, “The actors who I liked in this theater company, they went to school and got strong classical training and I want to do that too.” Because I love classical theater and I love poetry, it’s mathematical, it’s timing, it’s the things that I love about words. I ended up applying to this school based on knowing alumni from the school and some of the famous alumni from the school. Judi Dench, Laurence Olivier, everyone who’s in Black Mirror, all the many people who I went to school with are in Harlots and all this other stuff. It should have been a red flag when they were like, “How are you going to pay for school? Can you tell us your financial plan?” during the callback for the school.

[bctt tweet=”If your process as an artist didn’t involve sweating it a bit, your career milestones mean a bit less.” via=”no”]

I basically got loans for education but not for living. I was going to have to work and I did work. My mom was supplementing that. My stepdad lost his job, so they stopped sending me money and school became fucking hard. You’re at school from 7:00 in the morning to 7:00 at night, then you have homework which is memorizing and analyzing texts for hours. I was working on the weekends and stuff. I dove into this depressive tailspin of eating disorders and fucking horrible men. At the end of the first year, I left school. I stayed but then I did end up leaving but then I came to Los Angeles back home. I picked up the pieces and I did classical theater here. I ran a company. I wrote plays and I was fulfilled for that for a time. That’s the precursor to me starting comedy. At that point after having a failed classical theater, acting career if you will and dropping out of college, then a couple of years later, I’m a stand-up.

It’s interesting about stand-up as an art form is everywhere else it seems completely acceptable at the very least and oftentimes highly encouraged to get formal training. Whether it be acting, music, coaching in sports, obviously any higher education for the sciences, except stand-up. The idea that if you’ve taken a stand-up class, that is joke worthy, that’s ridiculous. I find that perplexing because the classwork can be an efficient way to pick up a lot of things and figure out a lot of stuff. Assuming two things are present, one is the instruction is competent and the other one is that your peers are competent, not all of them but enough of them.

It’s an interesting phenomenon within that and some of it is like, “That’s not how I did it, I was grinding it out and figuring that.” What if you could have taken a class and cut a year off of your learning curve, would that have been worth it? When I worked on The Humor Code, the book I published years ago, we went and sat in on a class here in LA by this guy named Greg Dean. You and Greg subscribe to the same idea which is the formulaicness of jokes. He has a system by which you can create jokes, at least a certain style of joke, and that once you pick up on that I can be useful. Especially seeing a lot of new comics construct jokes badly. That’s useful but it was fun, the class that we sat in on, my co-author and I. He was teaching crowd work, how to riff and how to do crowd work. You can learn how to do crowd work in a lot of different ways watching other comics, trying and failing, experimenting. He had some standard lessons and then in class people got up and got to do crowd work. Then they got feedback on their crowd work from him and from the crowd which I thought was fun. I’m the kind of person who would want to take a class.

I did take a class even though I hate school.

The third time this has come, hating school. We should talk about it.

I talk too much, I’m distracting in class, I get bored easily.

I love school and I have all those same things.

I got in a lot of trouble all the time for talking too much, distracting other people, being the class clown and that kind of stuff. I don’t like the politics of school and certainly in my schooling experiences like class and money, all those things sour. I’m like, “I don’t need this,” the world is tough enough. It’s battering my spirit in that way already. I don’t need to pay for the privilege of this reminder that I’m poor.

That sounds like a difficult inner dialogue to have. First of all, I agree with you. It’s not a level playing field but then the question is if you don’t play on the field, do you further disadvantage yourself?

I don’t know, if anything, I feel like my career is a slow burn. Everything I’ve gotten has been because I’m talented and I can do it. I wouldn’t change my experiences but money makes everything better. The stand-up class is the last thing, I’ve taken an acting class since then but I can’t pay somebody for that for me anymore. It’s like, “I don’t want to learn it.” I get disheartened by the experience and maybe I would benefit better from one-on-one tutoring on something if I were to go back to school or vocational training, I don’t know.

There’s an alternative model. There are two other ways to think about all of this stuff. This is in general not just specific for you. One is the apprentice model. I am a big fan of an apprentice model of learning. It’s alive and well in the sciences. At least it’s a hybrid model, if you go get a PhD at a research university in an area, in the social and natural sciences. You’re going to take some coursework and you’re going to get brutalized by it. It’s the nature of that thing but you’ll also be working closely with more senior people. At first doing the grunt work similar to being an apprentice in a peasant plumber for example, then as you get more experience and skill and show that you can do it, you will get asked and have the opportunity to do more challenging, more creative work. Until one day your mentor places his or her hand on your shoulder and says, “You can go do this on your own, grasshopper.” I don’t know how easy or hard it is to find a mentor in the arts. The other way to do it is to piece it together and the beautiful thing is that all the knowledge is out there and accessible. Is it a matter of can you curate it and do you have the discipline to systematize consuming it? Coursera classes, Khan Academy classes, YouTube, books, podcasts, Meetups, etc.

I wish that I had known more about that as a possibility but I did teach myself about stand-up that way. I worked day jobs where I could have headphones all day and I would binge all of these podcasts, listening to comics talk about comedy. This is true of a lot of comics of my generation and in this period of time, there’s been a slew of books written by female comics. I have listened to all of those as well. My friend, Kristal Adams, who has a podcast called Too Sensitive For Comedy, she talks about this but podcasts are the mentor now. That’s all of our mentors, there aren’t apprenticeships or mentorship. There might have been a time when somebody would be like, “You funny comic, come open for me on the road,” but that doesn’t happen as much anymore.

Openers are in the towns and it’s more cost-effective. What are those things that you are listening to, reading or watching that are good?

The book that I’ve listened to repeatedly is Joan Rivers’ Enter Talking. That’s her first book. It’s about the period of time just before she’s starting stand-up to when she does Carson. It shows her life and I love that book. I recommend it for anybody who’s female-identified or queered. Listen to that book because it is a good one. I loved Whitney Cummings’ book called I’m Fine… And Other Lies and Miss Pat’s book was also good. Miss Pat’s book was called Rabbit and that’s about her life as a teenage mother, a drug dealer who then turned it around and became a national headlining comic, how to deal with NBC and a TV show and all this other stuff but it was just interesting.

I have to imagine inspiring given your background.

Tiffany Haddish’s book as well, The Last Black Unicorn. That is a bit harder for me to get through sometimes because it just is, it’s difficult.

INJ 83 | Life And Comedy
Enter Talking

Tell me why? I’m about two-thirds of the way through it.

The day-to-day real nitty-gritty of what it’s like to grow up poor. Her situation was worse than mine. When she explains the stuff that happens with her mom and her mom being brain injured, that’s the stuff that gets me a bit. That’s hard, painful for me to listen to.

Talk about authenticity that’s on display in that book.

She’s somebody whose career will probably look like mine or I hope. We all knew who she was in comedy and then all of a sudden she’s a household name, her face is on billboards. I look to people like her, she’s not mentoring me directly. I met her, I know of her but I look to her as a mentor. I looked at Whitney Cummings as a mentor. I looked to Joan Rivers as a mentor, Miss Pat as a mentor. Cristela Alonzo, her book is coming out and it’s going to be in English and Spanish and I can’t wait to read that. I relate to Cristela’s story so much as well. I look to these women to see what they’ve accomplished and where they’ve come from and get on with it. It’s powerful stuff.

It’s interesting to hear this list of books because with the exception of Joan Rivers, there weren’t many resources if you were a young female comic in terms of looking for the inside information about this. Seeing, “We come from similar places.”

It’s finding the similarities between us all.

A few other things I want to chat about, do you have your notebook?

This is a change. I switched from a notebook to digital.

I’m an analog guy

I was for many years.

I love pens and paper. I’m sitting here with it.

I act to the same notebook in myself.

A Cambridge yellow legal pad, you have switched over to your phone? Tell me why.

I did it in preparation for the album to get everything ready for that. I’m concerned that if I’m going to lose these, if I’m going to keep them forever or what, I don’t know what’s going to happen to them. I make a lot of submissions for writing jobs and stuff. I keep all my scraps and notes for writing packets in my Google Drive. I can call upon any of them from the last few years and pull from them if I need like, “I’m going to need a plug-and-play joke, I need the beginning and the middle and I can just fix it. Do I have a joke about this person? I think I do, I remember writing a joke about this person.” I have it in my Google Drive, I should do that with my other joke so then it’s easier for me to recall them, pull them up or whatever.

The permanency, God forbid, there’s a fire or something like that.

I keep toting around all this shit from apartment to apartment but this could be digital.

It’s more of a European phenomenon than it is a US phenomenon at this point, this idea of digital nomadship. These are people who either sell everything they own or stick it in storage somewhere. Then live in the world with a bag, a laptop and a phone. When it is winter in Europe, they go to Bali and when it is summer, they go to Berlin or Stockholm and they’re working. The digital part of the nomadship is important. They’re working and can go to work anywhere as long as they have internet access. There is something about lowering your overhead, not just having stuff until you have to pay for a car payment or a house payment, but truly lowering your overhead so that you own almost nothing. It then allows you to be flexible, light, fast and live relatively cheaply. This is in that vein. Let’s finish by chatting about something early if you don’t mind. I can understand if you wouldn’t want to talk about it.

Like something that I haven’t finished?

[bctt tweet=”Jokes and timing are mathematical. You can say anything that when time it correctly, you make a joke out of it.” via=”no”]

Something you’re noodling on and you’re working on?

I have been talking about class slowly, I’ve been talking about my day jobs which for many years I was a property manager as well as I drove Lyft. Now I’m driving Lyft and not working in property management because it was too much of a time commitment.

The fascinating thing about Lyft in this city, first of all, Lyft, Uber, etc., make this city much more livable.

You could live anywhere in the city. You don’t have to have a car.

You don’t have a car in the city. The parking is half the problem. Everybody talks about the traffic but the parking is just as much of a problem. The other beautiful thing is it fits perfectly for the aspiring entertainer. You work when you want to work, you can turn it off once you get an audition. It’s freeing in that sense, I’m not suggesting its great work.

No, if I could be doing something else I would but it’s going to change come January though. The government’s making it that we’re not 1099 employees. We have to be employees. I don’t know how that’s going to change Lyft and Uber but for the moment until then, I’ll worry about that then. I’ve been talking about work stuff and this idea that somebody who I respected sat me down and spoke about myself and another comedian. They were like, “This person is fun on stage, are you having fun? Do you have fun when you’re performing?” I’m like, “That person owns a home, I am housing and food insecure. Sorry if I’m not bright-eyed, bushy-tailed every time I go on stage.” The class has been coming up a lot for me lately and I don’t have money. I’m putting things off because I can’t afford it. I’m living in a scarce moment in my life. It’s difficult to be and also that’s not the comedy that I do. I’m not fun, your best friend at the party. I’m your shitty mean co-worker. I have two notes here. I should combine them into one but what did you want to know about these pieces?

I don’t know, it is fun too. My bias is that I’m less interested in the final joke and more interested in the premise and development. Does it sound like your premise is about this idea of why you’re not?

It’s because I work two jobs. I’m building it out but I’m a property manager and I drive Lyft for a living because I love a white woman in crisis. It goes on to talk about this horrible tenant I had and then the second half of trying to figure out the best Lyft story to plug into it to balance set out. My process and this have been these jokes are an offshoot of this idea on the premise but you can scroll through it but I have a list of why I’m not fun? I go through like I have mental diarrhea, I have a mental breakdown on the page. It’s part of my process anytime I write jokes.

Number three, only men who want me love Naz or slow swimmers so they can’t trap me with a child. That’s funny.

That’s dumb as shit.

I like those two things together in the same. These are all the reasons you’re not fun?


My Target bra underwires snapped in half and I don’t have $20 to replace it. You’re brainstorming on what are the funny things.

I’m not having fun because an underwire was stabbing my boob, I would be funnier if my boobs were fully supported. I have that but then I keep trying to crack the premise, all start a thought. If you scroll through it you can see I’ll repeat a thought.

You have debt and you have bad credit, back-to-back?

I’m trying to get there and then lower on that page, part of the thing I do is I will make a list of points but then I also will set a timer and word vomit for twenty or fifteen minutes. Try to think of all the things, the rant that I would make if I were standing on the corner like a crazy woman.

INJ 83 | Life And Comedy
I’m Fine… And Other Lies

You’re like, “Of course I’m no fun. I didn’t get to take a car nap in between leaving my day job and showing up to the show.” That’s fascinating, you know that idea of setting a timer, I’ve heard a number of times. I had a comic on here, a friend of mine named Shane Mauss. He uses something called Write or Die. Are you familiar with Write or Die?

That is so scary.

Shane is a good joke writer and he’s committed to doing it. He believes in that. There are these different levels. For the reader, Write or Die is a website, you can go and use this program and you set a timer and you set a word count that you’re trying to hit. If you’re on pace to hit the word count, it rewards you, it makes nice sounds and, “Ding.” If you slow down too much, the screen starts to flash and it starts to make negative sounds. There’s some Terminator mode or something, I can’t remember. Annihilator mode or something I can’t remember what it is, which is that if you start missing your goal, it starts to delete the stuff that you’ve written.

I’m like a hoarder, I keep all the scrap. I keep all the bits, the half-sentence, all the versions of it. I want to keep them because that terrifies me.

I could see that. I’m not quite there yet either. I’m also am bad at doing the word vomit. I’m too meticulous, I want to edit and clean and make things pretty. Use words in fun ways which obviously there’s a place for that but it’s not when you’re developing something new. I hope that your Why I’m Not Fun bit becomes something. I also hope that like Bruce Springsteen and Tiffany Haddish and all these other folks that you get to a level of success that then becoming fun is more of an option. You could decide, “It’s time to be.” That’s great. Thank you for doing this.

Thank you for having me, Peter.

It is super interesting. Thanks. Cheers.

Resources mentioned:

About Madison Shepard

INJ 83 | Life And ComedyMadison Shepard is a stand-up, writer, and actor. She’s appeared on Comedy Central’s The New Negroes. She’s performed at The S.F. Sketch Fest, Broke LA, and Laugh Riot Grrrl Festival. She studied acting at Los Angeles County High School for the Arts and The Royal Central School of Speech & Drama, in London. Madison is soon to release her debut EP “Goodnight Silverlake.”


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