Skyler Higley Will Inevitably Get All the Trophies

This week, we’re highlighting 24 talented writers and performers for Vulture’s annual list “The Comedians You Should and Will Know.” Our goal is to introduce a wider audience to the talent that has the comedy community and industry buzzing. (You can read more about our methodology at the link above.) We asked the comedians on the list to answer a series of questions about their work, performing, goals for the future, and more. Next up is Skyler Higley.

Tell us a story from your childhood that you think might explain why you ended up becoming a comedian.
I’ll give you two: The first is a story that I am told happened when my adopted mother (white) brought me to church (Mormon) for the first time. All the churchfolk were gathered around my baby carrier, and I was covered with a blanket, and when my mom did the big reveal, one of the Elders exclaimed, “Oh, wow, that baby’s a Negro!” Which does a decent job of establishing the alienating context that I grew up in that would lead one to seek comfort in comedy.

Luckily, as weird and at times traumatic as it was, that context can be exploited for laughs, like in high school when I ran for student-body secretary (the school wasn’t ready for a Black president). I was a lot less popular than the person I was running against, so I worked hard to make all my campaign videos really funny. Once we did our assembly to present campaign speeches, I essentially just did stand-up and closed with “I’m Skyler Higley, and if you don’t vote for me, you’re racist.” I got sent directly to the principal’s office after, but I also won. Pretty clear trajectory there, I’d say.

If you were immortalized as a cartoon character, what would your outfit be?
I’d like to have a cool jacket on. I don’t know if the character would wear glasses, because I alternate between glasses and contacts depending on where I’m going to be. As a Black man, the choice to wear glasses directly affects how smart/cool people perceive you as, and they’re inversely correlated.

You know what? I’ve decided my cartoon would just be me as the Jim Crow caricature. Everyone will be like “What the fuck!?” But the joke’s on you, because then I get to be in history textbooks.

What’s your proudest moment/achievement of your comedy career so far?
When my former boss Conan O’Brien pulled me aside and said “You’re by far the most talented person I’ve ever met.”

Having been a staff writer for The Onion and Conan, I do recognize that I’ve lived a lot of Gen-X white guys’ dreams. Being a part of the end of Conan on TBS was very special. Getting to know and work for a comedy legend that you grew up a fan of is really exciting. Once, he emailed me complimenting something I had written, and I emailed him back, “This is a big deal coming from you. Ever since I saw Conan O’Brien Can’t Stop when I was 14, I’ve been a huge fan of Jay Leno.” There were a lot of media outlets that ran retrospectives of his career on television, and to be mentioned in some of those, even as a very small footnote in that legacy, felt cool. I was only there for the final season, which is a little like taking a paddleboat out to the Titanic to hop on right as it’s sinking into the water. But then you get to say you were on the Titanic, which is legendary. And I got a nice little trophy, which is what it’s all about.

I will say that building up career achievements as a means to validate ourselves as artists is fraught, since these achievements are the result of the mechanisms of an industry and, therefore, the whims of a bunch of psychopathic rich people in conjunction with a mysterious algorithm designed to optimize stealing our souls. Don’t get me wrong: I desperately want to be more famous but also believe that success is inherently meaningless*. That said, I do intend to get all the trophies. Also, please don’t tell Conan I compared working on his show to being on the Titanic.

*Success is meaningful based on the concept of value within our collective neoliberal psyche, but fuck all that shit, man. Open your mind!

Which comedian’s career trajectory would you most like to follow?
This is a trick question. Pass. How can you really answer this when career means something different than it ever has and the media landscape and the world that created the comedians that I love doesn’t really exist anymore? I have tons of aspirations, but isn’t it kind of useless to worry about emulating what anyone has achieved in the past if all your goals are in the future?

I want a few good stand-up specials and to write a few good movies, one great show, one book; and I want to die in a spaceship accident on the way to the moon. And fine, if you want me to just give you the type of answer you wanted, I’ll just say Roy Wood Jr. and Jordan Peele. There. Are you happy? Stop yelling at me.

Tell us everything about your worst show ever. (This can involve venue, audience, other acts on the lineup, anything!)
The venue was somewhere in the South, where I probably just shouldn’t have been booked. I wasn’t ever going to draw a crowd, especially there, so not only was the venue pretty rude to me about promoting, but they also promoted me with made-up credits that they thought would be more attractive to their local crowd. The post on the website said “SKYLAR HIGLEY: Seen as Ringleader at UniverSoul Circus and on BET’s Comic View.” (For what I’m going to assume is the average Vulture reader, UniverSoul Circus is a Black circus founded in the ’90s, and BET’s Comic View was a stand-up showcase hosted by people like D.L. Hughley and Cedric the Entertainer that also started in the ’90s.)

I was supposed to do five shows that weekend. I had only sold 15 tickets total, but of course there would be some walk-ins. The first show went a lot better than I thought — pretty good, in fact. But then there was the second show, which was so bad I think that the CIA could use experiencing it as a form of torture. I bombed for 40 minutes straight. The few handfuls of people who did buy tickets at the door heckled, made high-pitched “bomb-dropping” noises after every punch line, and walked out during the show talking shit about how bad I was and refusing to pay for their drinks. I’m pretty sure, given the situation, I would’ve bombed anyway, but it was extra bad because this was an older, Black-ass room, and I can only code-switch at about level five, and I needed to be a level ten, at least. They wanted Bruce Bruce, and unfortunately I am not Bruce Bruce. (To the people at Vulture, please do not make my blurb headline “Skyler Higley Is Not Bruce Bruce.” I’m so serious I will be upset.) It really sucked.

Obviously, there was a lot of shame and embarrassment about being “Black enough,” and we can have this whole conversation about Black essentialism and being perceived as valid or not and blah blah blah, but at the end of the day, it doesn’t matter how well thought out I am about race or culture; comedy is visceral, and if the crowd doesn’t like who you are, there’s nothing you can do. The club canceled the rest of the shows that weekend, so I spent the rest of the weekend in a hotel room depressed about my existence (see question No. 8) and truly resentful of how many comedians also would’ve bombed in that situation but would never have been booked there or have to deal with issues of being an outlier in this way. I could write a whole essay on that show alone, but I’m cutting myself off. Read Black Skin, White Masks, by Franz Fanon, and listen to “Not Like Us,” by Kendrick Lamar.

What have you learned about your own joke-writing process that you didn’t know when you started?
I realized relatively recently that a lot of my “process” when it comes to stand-up is literally processing trauma, but I don’t think that’s anything new for a comedian. I also learned that if I’m actually sitting down to write, the feeling of I got nothing, I’ve lost it, I’ll never write a good joke again is simply part of the process, like the resistance that a space shuttle has to push through to break out of the atmosphere. All I have to do is let that spiral happen and steer into that skid, and the voice in my head that screams Not good enough! and the part of my brain that goes What about this? have a righteous battle between dark and light for a thousand years and then, hopefully, the result of that is a joke that I can feel satisfied with.

I’ve also realized that I’m a little synesthetic about ideas — not in the Pharrell-Kanye way, but I do tend to think about concepts in terms of shape and color beyond the concrete rhetorical level. (Maybe everyone is that way and I’m just articulating it, or it’s the result of drug use.) Especially for my own personal writing, as opposed to job stuff, I kind of always have a specific shape and colors I want to feel. Is this making any sense, or is it abstract to the point of self-indulgence? Whatever. Sometimes I’ll think of jokes in dreams. One I remember is: “Why do we even have moments of silence? They don’t work! They’re staying dead whether we’re quiet or not.” In my dream, that killed.

What’s the biggest financial hurdle you’ve encountered since becoming a comedian?
I saved up money to move to Chicago to start comedy, but then I was broke as hell until I started getting writing jobs. At one point, I tried to drive for Uber, but I spent all my money buying a super-cheap used car, and the dealership was really shitty, and the car started having problems after a few weeks, and I wasn’t getting close to enough rides to support myself. That was one of the few times throughout my early 20s where I played that game Rent or Food?

I have a few resentments that I can’t let go of when it comes to comedy, and they’re all related to privilege. First is the amount of creative latitude white comedians and writers receive off grip. Second is when a comedian is really hot, because, Why are you that hot? Stop it. Third, and the one I resent most, are the ones who have been unburdened financially their entire time pursuing a career in comedy. Which is why I want to see what everyone else wrote. Who on this list has secret rich parents? When the nepo children make it on this list, do they answer this question?

At the end of the movie 8 Mile, Eminem’s character, B-Rabbit, starts his final battle rap by dissing himself so the person he’s battling has nothing left to attack. How would you roast yourself so the other person would have nothing to say?
Hm, not sure, guess I’d probably say something about … being a skinny-ass, corny, gap-toothed, tries-to-project-being-smart-to-overcompenaste-for-being-whitewashed, discount Donald Glover who’s on his fifth rewatch of Cowboy Bebop. I don’t know, something like that. I’m a very easy target for roasts. Everything is really on the surface. “Mormon” and “adopted” were already pretty popular/hackneyed punch lines by the time I was born, and yet those were just factors of my life, so when you think about it, it’s kind of like my entire existence is already a joke. But so is everyone’s.

When it comes to your comedy opinions — about material, performing, audience, trends you want to kill/revive, the industry, etc. — what hill will you die on?
See, Vulture, you could’ve made this whole article this one question. Here’s a list within a list (meta!):

• The majority of older, famous stand-up comedians should retire. They’re not offering anything that insightful or well written. What they accomplished was great, but like with superstar athletes, there is a point where they simply can’t be good anymore. Imagine if Jordan kept playing for the Wizards but also every shot he made had to be about “cancel culture” or trans people.

• A lot of alt-comedy is great, and I do like it, but it is often the creative result of privileged performers (maybe white) being able to sidestep their lack of perspective or struggle by being whimsical and weird.

• Material should be memorable and not only functional.

• The internet has changed the value and form of comedy, and it’s become very easy to be creatively lazy, which is strange since we have the tools to make things very well. The constant demand to not only write stand-up all the time but to put everything on social media makes me feel like I’m dumping more shit into a river of shit.

• This industry is absurdly exploitative and psychologically damaging. Whether you want to or not, being in it means you’re involved in a game of power and hierarchy that is all built on ego, which incentivizes being a narcissist.

• Comedy is simultaneously better and worse than it’s ever been.

• “Funny” is subjective, and this myth of “being able to kill anywhere” was made up by comedians who actually didn’t perform at a lot of places.

• Comedy can be a liberating force, but isn’t inherently moral or liberating.

• New York is better than L.A.

• Comedians coming up now have to work a lot harder than they ever have before.

• There are a lot of amazingly talented people who could be making some great stuff given more opportunity.

What is the best comedy advice, and then the worst comedy advice, you’ve ever received?
I think the best advice is to remember to have fun. Obviously don’t just have fun; it’s work. As comedians, we are turning fun into work (or working to create fun? I don’t know). But while being a comedian and pursuing it as a career, you can start not having fun very quickly without noticing, usually because you’re caught up in what you have vs. what you want, or the way things are vs. the way they could be. And you’re right to feel this way, because it does suck (the industry, human life, society, take your pick), but try to have as much fun as you can relative to how much everything sucks.

Most of the bad advice I’ve gotten I’ve instantly deleted from my brain, but I do remember advice that wasn’t technically the worst but contextually terrible. Once upon a time, I had a great set, and afterward a very famous yet truly awful comedian came up to me and was complimentary about my writing, but then said, “What you should really do instead is go up there and just talk.” Now, here’s the thing: I love riffing. I do it a fair amount. It’s great because it can connect you to the crowd and bring everyone into the moment more than simply just performing jokes. That said, this comedian then went up to a hot crowd and proceeded to “just talk” and just bomb harder than I would’ve thought possible, ruining the energy of the entire show. So yeah, you should also write fucking jokes.