What Does it Take to Write for Stephen Colbert?

Chelby Joseph
Sep 28, 2020 · 21 min read

Chelby Joseph (me) and Bianca Brutus interviewed Felipe Torres Medina, writer for the immensely popular late night show, The Late Show with Stephen Colbert. Felipe is a comedian of color who gave us an inside look at what it means to be a comedy writer in today’s social climate and priceless advice on what it takes to be staffed on a comedy show.

This interview is a part of our new series with New Yorkville where we interview successful comedians of color and get their stories to share with you.

Can you tell us a bit about yourself?

Image Courtesy of CBS

When you came to the U.S., how did being an immigrant impact the way that you wrote your comedy or change your comedy process in general?

I wanted to be seen as a writer, as a comedian. Period. I didn’t want to make jokes about immigration. I was not going to be the guy who came to America and made jokes about coming to America. I think there was a big part of me that was like, “I don’t want to do that. That’s not my sense of humor. That’s not the kind of comedy I like or the comedic sensibilities that I have…” and then it absolutely was! Part of it is the mix of what you experience as an immigrant and the strange injustices that are so absurd that to me — who uses comedy as a defense mechanism — translated into comedy.

For example, there’s a person in the United States who has a certain combination of names like mine. I am Latino, so I have four names: two first names and two last names. There is someone in the United States who is a criminal who has the same combination of names or some modification of them. When I was applying for my student visa here to come do my masters, the American guy who held my passport at the U.S. embassy was interviewing me through a phone like, “This was a jail and through the glass is the United States. Outside of the glass, you’re still in Colombia.” This guy was holding the phone and he had my passport and all my documents that said, “ This guy has been accepted into a program, this guy is allowed to stay here, and all that stuff.” Then he looks at my passport and goes, “Have you lost 200 pounds in the last three months?” No, of course not! But a guy who had the same, weird combination of my names was also some three hundred and something pound guy who had murdered his wife and his mother in law in Miami, Dade County.

I was thinking, “Sir, I am a 20 something bourgeois little boy from Colombia. I am not this murderous monster man.” When those absurdities become your experience in your life, then it almost became inevitable that I would talk about it in my work.

Many of my anxieties as an immigrant were, “will I get to stay in this country?” It also so happened that I started my comedy career around the same time that Donald Trump launched his campaign and eventually became president. He launched his campaign by saying that Mexicans are rapists and murderers from day one and we [immigrants] were like, “this is messed up” and everyone else was like “hahaha.” It’s kind of thrust upon you, but it’s also something that I chose to make part of my comedy. I think it results in a sort of observational comedy that only outsiders can provide. When you grow up in a certain system and see certain things as being the natural order, but then when you come from outside, you’re the person who can say, “the imperial system is fucked up…” Why don’t you guys use metric? It makes absolutely no sense.

Chelby Joseph: Yeah, I completely agree. There are so many things that I wouldn’t even recognize as strange until someone who came to the U.S. pointed them out to me so that’s really great.

Felipe Torres Medina: Yeah, and it’s not just immigrants, right? People who are not represented in popular culture or mainstream comedy decoded things in a different way because society itself is different for us, so we get to see the world differently and get to turn that into whatever our art is; whether it’s comedy or horror or poetry or whatever it is.

I think that the great beauty of this country is that it can contain all of these different people. You can have Hasan Minhaj and Jordan Peele and they can both do very different types of comedy than say Ali Wong. They’re all different, but they’re also real and funny in their own way.

They can all describe America with their own artistic vision in a way that’s exciting and true and genuine. It doesn’t mean, “well, this is the Black vision of America.” No, it’s not that or, “this is the immigrant Latino version of America.” No, it’s just that this person is using their experience to interpret art.

Bianca Brutus: Wow, as a child of immigrants myself, I found that sometimes when comedians would be immigrants, they’d have to play out to a white audience and stereotype our accents to get the laugh and I always found that despicable. So, I never looked at it that way.

FTM: Yeah, there was a big part of me that was like that when I first came here. I’m not the guy who’s going to put up an accent and I never put an accent on stage. I’ve done characters in sketches that will do that, but I’ve never gone on stage like, [with accent] “Hello, how are you?” That’s not my accent, that’s not how I speak, so that’s never what I want to do, but I think it is learning to subvert the expectations. That’s what comedy is, just subverting expectations. Learning to subvert the expectations of that white audience, I think, is something that’s very fun. I once wrote a joke — I’m going to completely botch it because I haven’t told it in forever — but I used to tell a joke about John Wilkes Booth. I would say, “John Wilkes Booth was an actor. A bad actor actually…but that last performance killed.”

It’s funny because in mostly white audiences, some people boo and some people groan. I mean, it’s a groan inducing joke, but then I say, “I know too soon. I know too soon. 1866 is too soon.” But I know it’s actually 1865 and what I say then is, “I want to apologize because I said 1866 when I should have said 1865. I want to apologize to all of you because I know that you guys would never mess up the exact date of the assassination of Colombian leader Jorge Eliécer Gaitán, so let’s all say it together. April 9th…”

I’m just taking that expectation of saying the wrong date, but then correcting myself and twisting the game upon their heads and making the audience aware of how they are ignorant. How I, as an immigrant, had to learn these things about Abraham Lincoln is a good way to poke fun at the white audience because that white audience is going to be the majority of people, even in a city like New York that’s very diverse.

When you were growing up and learning about comedy, who influenced you? Did you find that you liked a lot of Colombian comedians or did you look to America a lot?

So we watch that and The Cosby Show — speaking of shows that do not hold up. We would grow up watching that and also the Latin American, Colombian, sense of humor. I think that Colombians have a very particular sense of humor that sometimes can be a little mean, but it’s never mean spirited. It’s because that’s kind of the humor and the humor is meanness. There were a few Colombian’s that I obviously enjoyed watching and then there was this Argentine group who were a musical comedy troupe called Les Luthiers which is a French word because they designed their own instruments. It’s the word for a violin maker and they created their instruments out of trash and things like that. It’s a little bit like Stomp mixed with classical chamber music because they were all trained musicians, so they were hilarious! I’ll still sit down and watch their videos on YouTube that are 30, 40 years old and crack up. I think they’re the funniest shit in the world. They were a huge influence.

Then as I became a teenager, we started getting the American shows on TV. I discovered Letterman and Saturday Night Live. We actually got SNL and Letterman three months late and not live. So Saturday Night Live was Saturday night for sure, but three months later and half of the sketches were cut for time because it was only a 30 minute slot instead of an hour and a half. Then, there was only one musical performance. When I moved to the States and I was like, “Wait…the musical guest does two songs, this is insane!”

I think that people who say that SNL isn’t funny anymore are wrong and it’s just curmudgeonly people stating, “I liked it when I grew up watching it.” But obviously I grew up with Tina Fey, Amy Poehler, and a little bit of the Will Ferrell generation.

CJ: That’s a good group!

FTM: Tina Fey, Amy Poehler, and Seth Meyers started that era, then came Bill Hader and Andy Samberg and Kristen Wiig. We thought, “holy shit, these people are amazing!” But as you can tell from the names I’m saying, none of these people are people of color.

I think I was seeing these people and not feeling particularly represented in any way. Not that I understood what it was to be represented in shows. I remember there’s a sketch where Amy Poehler plays the dollar that’s been devalued and Seth Meyers walks in with a top hat and he’s the British pound and Maya Rudolph comes in yellow face — I think she’s the yen. Then, Horatio Sanz comes in with a sombrero and he’s the Mexican peso. Even then I thought, “Oh, man, this is not great…”

However, at the time you just attributed it to something that’s still true. “That’s just Americans.” They don’t see the world outside of America. They just see the caricature. I would say that’s the evolution of my influences. Obviously around that time when we got the American shows in Colombia, I started watching The Colbert Report and The Daily Show, which at the time were the biggest thing so that was very cool.

CJ: That’s such a good point about Saturday Night Live though. They do not have a good track record when it comes to being racially inclusive.

FTM: They don’t! They just hired their first Asian performer ever this season and he’s fantastic! Bowen is incredible, but it’s almost as if, “you missed out on people like Bowen for 40 something years.”

Image of Bowen Yang Courtesy of Vulture Magazine

When you have a culture that only values or uplifts the white comedian, when you’re in the writers rooms for these shows, how do you navigate being a person of color and do you feel as though you have to censor yourself?

It was a small master’s program — that’s part of the appeal that it’s 6 to 10 people in every class — but there were only two people of color and those were a black woman and me. Again, I think the world has come to a big reckoning in the past 4 to 5 years and I think that when I arrived here, there was this feeling, I think, of America that “We have Obama as president and racism doesn’t exist anymore.”

Now, if I told the people who were in my M.F.A. program the things that they said to me that I thought were hurtful or offensive, I think they’d respond, “Oh my God, I can’t believe I said that!” I think that if we talk about systemic racism, then we have to believe that not every action that is racist is evil or something that people are trying to do just to destroy you.

Obviously, racism is evil, but I do believe that certain things that people say just come out of ignorance. I think five years ago, people would make jokes or comments that today we might say, “what the hell,” because of the lack of inclusiveness. It’s diversity and inclusion, right? They got better at diversity, but they didn’t work on inclusion. They didn’t work on including people of color in the institutions. They have the faces there, but they didn’t have them in positions of power where they could say, “this is not okay.” It’s a process and people didn’t know that was bad.

I feel that we have to cut people a little bit of slack sometimes and say, “Yeah, I know you messed up. It’s good, we’re good, but you have to know that was bad.” It obviously doesn’t mean you’re an evil monster — and it depends on the action, obviously. If they are violent, then yes, fuck you.

I can say navigating these spaces can be complicated, but I think people in most comedy rooms that I’ve been in — and I’ve been very lucky — have been very receptive. If there’s any instances of things that have made other people uncomfortable in any way, they tend to get resolved quickly and directly. The people that I have the pleasure to work with and collaborate with have never turned defensive. They never state, “Well, I didn’t mean it like that. You’re being too sensitive.” It’s always, “Oh my God, I’m so sorry! Thank you for letting me know.”

I think it’s important. I’m a straight man so there’s things I might say or do that are hurtful to other groups such as women or LGBTQIA people.

BB: I’m glad to hear that as sometimes these writers’ rooms or these institutions pride themselves on diversity and inclusion and have these diversity scholarships — which are pretty much about tokenism — and at the same time, they’re actually doing nothing necessarily to help the people of color on their team. When those people come forward about things that make them feel uncomfortable, they always brushed to the side. It’s amazing to see you’ve been able to find that space where you feel accepted.

FTM: I’ve been very fortunate and I know that that is true. I don’t mean to minimize or deny any of the things that I know have been in other rooms, but I have been incredibly lucky.

BB: That’s amazing!

How have you been able to handle rejection?

You’ve got to learn to deal with it because you’re going to get most of the stuff you write rejected. Every morning you have to go down to the joke mines and try to get some jokes out of there.

This is obviously not comparable to actual arduous labor, but if you go down to a mine, you’re not going to find a nugget every day and you’re not going to find the precious diamond every single day, you’re going to do work and try to turn that coal into something else. For the most part, finding a beautiful gem in the middle of this everyday is hard. So I think a lot of it is dealing with the reality that not every idea is genius, but it is all part of the process. I write for The New Yorker and McSweeney’s, but I’ve been rejected more times than accepted.

When you work on a show that’s daily like The Late Show, you learn not to wallow in the failure of rejection. This is something that I remember Seth Meyers said in one of his very early shows when he started doing Late Night. He used to be the head writer of SNL and he had a whole week to think about how bad a sketch had gone and how poorly it had been received. He had a whole week to think about that while planning the next week’s show. He was doing Late Night and he was doing a show every day and that just robs you of that time to wallow in self-pity and sadness.

It can be very frustrating and hard. This is not to say don’t feel sorry about yourself because you should be allowed to feel sorry about yourself and to feel like, what am I? Is this ever going to happen? Also, keeping yourself busy with more projects is the way to learn to deal with that stuff. Sometimes it can feel that you had the best idea and it got rejected, so, what’s the point? Then, you can have others. It’s the shows that are daily that teach you to obviously appreciate the highs, but not to spend too much time celebrating them and to not sit with the lows for a long time because it’s going to happen. It’s part of the business.

CJ: That’s really great to hear you say, because when I’m doing stand up comedy, whenever a joke doesn’t land, I think, “Wow I’m just not funny.”

FTM: It’s something that’s going to happen every day in every space even from the most amateur, greasy, back door, makeshift theaters like the Triple Crown. If you bombed there, you’re going to bomb in a professional writer’s room.

Speaking of improv, what do you think is the future of comedy clubs? If you don’t have an indoor venue, mostly during the winter, what happens then?

It’s very sad, but I feel that UCB was poorly run. It wasn’t just a pandemic, this was a poorly run business. It created a very cool community, and I hope that the people who were part of that community are figuring out and working together to come up with new spaces that are more diverse, better run, more open, and less secretive. UCB, as most comedy institutions and cultural institutions, tend to be very secretive. Obviously what you would want for the future is that these clubs and these places are allowed to exist, and we learn from the mistakes of the past and make them more democratic.

We know that you are part of the sketch house team “Night Eaters” at UCB. Could you talk about your experience being on that? Do you still work with your team?

As for Night Eaters, everyone is shooting sketches or videos from their house, but they’re great people. The most important lesson that I learnt there was in our first meeting ever with our director. She said, “Look around this table, these are the people who are going to get you a job because it’s not going to be Lorne Michaels or Trevor Noah. These are the people who are going to work with you every week for a year and know your sensibilities and be able to vouch for you or say this person is so funny and they’re going to put your name in.” Obviously, getting a comedy job is not like name dropping. You gotta work to get it, but the word of a writer on a show goes a really long way.

Image Via Night Eaters Comedy

Caitlin Bitzegaio, our director, saying that was eye-opening for me. In a sense I already knew that, but verbalizing it made me feel that the most important thing I could do is work on my material to make it the best that it can be, and that’s what’s going to get me noticed.

It’s not going to be that you’re doing stuff to get noticed, you’re going to do stuff to do good stuff, and that’s going to make people take notice. The people you work with are going to enjoy working with you if you do something for the sake of making it amazing.

In terms of getting esteemed jobs in comedy, do you have any advice for people of color who are trying to do what you’re doing?

If a friend of mine works on a show and they’re shooting a sketch, they can say, “I know an actor who would be perfect for this.” My advice is finding those people you can be vulnerable about your art that you ask them “I don’t know if this is any good, can you give me notes?” and doing the same for them is going to make both of your works better. Eventually, one of these people in your crowd is going to get a packet, which is how most of these shows work, but they ask you to submit a packet and what you should do, which is something that I didn’t do at the beginning because I had this competition mentality is share those packets, send it to your friends and start working on it, but you’re not going to have all the answers on how to write this packet. It’s a hard thing to do, but that’s just going to make your packets better and it’s going to make you feel better about the whole process.

You’re not alone. Find people that you can trust, that you can be vulnerable with about your comedy because the truth is once you get into a writer’s room, collaboration is key. They’re not going to hire you so you can write your jokes every day because of your name. My name is not the one on the marquee at The Late Show and the same goes for The Tonight Show, Full Frontal, or The Daily Show. That’s Jimmy Fallon, Samantha Bee, and Trevor Noah. When you’re in that writer’s room, your jokes are not going to be the be all end all. You’re going to be sitting down with a group of people who are going to try to come up with the best jokes that day, that’s why collaboration is so important.

Do you have advice for any person of color who’s probably sitting at home and wants to do comedy but is fearful that they won’t feel welcomed, accepted, or that their jokes won’t land?

Well, to start, the jokes probably won’t land at the beginning, because might I say from firsthand experience, they don’t. The first step is to find what makes your voice feel best and makes you feel most comfortable. I started doing sketches, and that’s still what I think I’m the best at. It’s all about finding that thing you like the best.

If you’re a person of color going to these white dominated spaces, go ahead, go all in, and try everything. Try every single avenue and find out what makes you happy because people are going to be mad regardless. Find the things you love or find inspiration from watching other people. If you love The Onion and think Onion headlines are the funniest form of comedy, then try to write Onion headlines every day and don’t show them to anyone or later show them to someone that you trust. Don’t write headlines for the sake of going viral, go write them because they make you laugh, because eventually you’re going to find The Onion has submissions. There are so many publications now. There’s Points in Case and there’s The Belladonna — that’s just for female identifying people.

I think just try and find what you find funny and then put it to paper or to stage or to whatever that you think is best, if you can make a funny Tik Tok and go for it. I go on Tik Tok and these videos are hilarious, but I could never do one. I found that I’m good at writing sketch and humorous pieces, and I love giving silly voices to stupid characters, but that took me years, and I’m still learning. I write jokes every day from my job and I still wonder if I’m best at this particular kind of monologue or joke and the only way to do it is overcoming the fear of rejection, doing it, and knowing that it’s going to suck a little bit.

It’s very trite, but there’s that famous Ira Glass speech about taste. To paraphrase, The thing about being an artist is that you love art and you love to appreciate whatever form of it you’re doing. It could be comedy, painting, sculpting, whatever you love. It’s art and you love to see it, and you want to do it. You have great taste because you are an artist and you have been watching other great people do great art. So your taste is that this is good art and then you start doing your art and then there’s a gap between what you’re doing and what you want to do and you know it because you have taste and you know that your good taste tells you that this is great and that what you’re doing is not quite there. Basically, our struggle is to continue to try and fill in that gap, to get us close to what you want to do with what you’re actually doing with your art. And it’s an endless struggle, but the only way to get better is to just do it.

CJ: Felipe, thank you so much! I feel as though you’re inspiring a new generation of comedy writers because I’ve never talked to a comedy writer of color. Maybe as a final question.

Do you have any side projects that you’re working on?

BB: No side hustle on Tik Tok?

FTM: No, I’m going to leave that to the experts: rich white girls from the Midwest who have giant houses.

CJ: Right? They’re all so wealthy!

BB: Oh, congratulations on your Emmy nomination!

FTM: Oh, thank you so much. Yeah, it’s crazy, but it was very exciting.

Do you know how the awards will go?

BB: You should still wear a tuxedo. I think it’s okay!

FTM: I told my wife I’m going to wear one of those t-shirts that have a tuxedo on them. Again, thank you so much for having me! This was very enjoyable and I hope to help out in any way I can.

As I said earlier, you’ve got to democratize these institutions. The more people who look like us that get in writer’s rooms and in any position, really, the better.

Follow Felipe on his Instagram and Twitter accounts or visit his website to keep up with his next projects and humor pieces.

New Yorkville

The Comedy Club for Comedians of Color

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The online comedy club that highlights the hilarity of comedians of color. Interested in sharing your work? Click ‘Submission Guidelines’ and give us something to laugh about!

Chelby Joseph

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In my proverbial salad days

New Yorkville

The online comedy club that highlights the hilarity of comedians of color. Interested in sharing your work? Click ‘Submission Guidelines’ and give us something to laugh about!