When her first book, So You Want to Talk About Race, landed on the New York Times bestseller list earlier this year, Ijeoma Oluo cemented her status as a thought-leader of our cultural moment, surprising exactly zero of her many readers. Oluo’s laser-sharp, direct tone has made her a popular writer and speaker, whether she’s tackling issues of race, social justice or feminism, or making one of her beloved makeup tutorials (seriously, they’re fantastic). Her writing has been featured in The Guardian, New York magazine, Jezebel, TIME and many other outlets including feminist website The Establishment, where she serves as editor-at-large.
If you’ve spotted a bushy beard at a local comedy show in recent years, chances are it belonged to Emmett Montgomery—unless that show was in December, in which case it could have been Montgomery’s Santa-obsessed alter ego, Sugar Plum Gary. For well over a decade, the Utah-bred comedian has been cultivating spaces for odd, risky fun times on Seattle stages, from his long-running monthly show Weird and Awesome at the Annex to The Magic Hat at the Rendezvous, an “evening of storytelling, songs, jokes, weirdness and participation” that he has dubbed a “friend-making machine.” Montgomery has also performed his own kind-hearted standup all over the city and the country—and on season 9 of Last Comic Standing.
The two got together at Beacon Hill’s new Clock-Out Lounge, where Montgomery cohosts the weekly Joketellers Union, and they proceeded to talk in earnest about the importance of holding space, the local comedy scene, the challenges of writing on social justice issues and Seattle’s problem with paying for art.
This interview has been edited and condensed.
IJEOMA OLUO Remember when we spent a year trying to have coffee? And we just couldn’t make it work. [laughs]
EMMETT MONTGOMERY Yeah. And then was it your housewarming or your birthday or something? I was all ready to go and then something happened.
IJEOMA It was earnest trying, too. It wasn’t Seattle-nice trying, like, “Oh, we’ll do a thing.” We would get the date and the time and then something would come up.
EMMETT And all you can say to people is, “Don’t stop.” Thank you for this desire to include me, please keep including me.
IJEOMA There are people who I don’t encourage to keep inviting me to things.
EMMETT Yeah. I see all the emotional labor you’re doing, even just in the people who are so invested in your life, maybe too invested in your life. Years ago, my brother and I were at a bar, one of my six brothers, and we were just eating corn dogs, and this woman comes up with these two pugs—I was very excited. And she goes, “Oh, hey Emmett, how’s it going?” and I did not recognize her. She goes, “Oh, is this one of your brothers? Which one is he?” Then she’s like, “How’s [your wife] Kate doing? How’s [your chihuahua] Donna doing?” And my brother goes, “Oh, how do you know Emmett?” And she goes, “I don’t.” And I’m holding one of her pugs. “I’m just a fan.” Just…wow. But do you stop opening your heart and telling your story?
IJEOMA It’s hard. Some of it becomes really intrusive, but some of it is so special and so wonderful. Some of it’s really awkward, especially since I write about race. So a lot of people will stare at me and then they’ll be like, “I have a Black husband,” and I’m just like, “I don’t want to have whatever this conversation is.” [laughs] But sometimes it’s just people being friendly or fun or sharing a little thing. And then some people are scared to do that and I feel really bad. I’ll be grocery shopping, and then I’ll get home and there’ll be a Tweet mentioning me like, “I saw Ijeoma in the grocery store, but I was too afraid to say anything.” And I’m like, “You can say hi. It’s OK.”
EMMETT Yes. Hi is great. But demanding justification for your feelings is not, necessarily. Last year, cut.com recorded me talking about my dead cat, Walter, that I talk about all the time. And they did some animation and cut together this seven-minute storytelling video that went viral. All these people reached out, and some of them were sharing very beautiful stories, but a handful of people got really upset that I didn’t respond—and it went viral on my eighth wedding anniversary, so the last thing I want is to talk to strangers about my dead cat while I’m trying to have a romantic and lazy day.
IJEOMA Eight years? So that means I probably knew you before you got married?
EMMETT Yes. I think it’s about a dozen years or so?
IJEOMA Yeah, and you’ve stayed in my life all this time. I’m not an incredibly social person, but there was this time in Seattle where I would go to things, especially when [my brother] Aham was doing comedy, and you were doing comedy, and there were so many people in Seattle doing these really fun collaborative projects.
EMMETT Which is still happening!
IJEOMA Yeah, they are. But I stopped going [laughs]. For me, that’s still a really special time. I do catch you occasionally in things, and it’s really fun to watch because you’re not the same comedian you were back then.
EMMETT No. I hope I’m not! You’ve got to be a shark. You’ve got to keep swimming.
IJEOMA And you have. You’re so good now. I’m not saying you were horrible then, but I remember that time…
EMMETT I took a lot of weird risks.
IJEOMA We would all be like, “What the fuck is happening here?” Sometimes you’d leave going, “I don’t know what that was.”
EMMETT That space is important. And I have to remember all the mistakes I made. We had that golden time where everything just worked. And then it stopped working. And people can either mourn that time that will never come back, which I think a lot of comedians of a certain age do, or you can ask, “What were the best parts of it?” It was the ability to take risks, the communities that formed, the fact that people were doing comedy that were told that they shouldn’t do comedy. How do I recreate that and maybe create that golden time for other folks? Remembering some of the weird shit I did—man, I shit on a lot of stages. And so, maybe part of my life now as an adult is creating stages for people to poop on.
IJEOMA You’ve been through some of the darker times in Seattle comedy.
EMMETT It stopped being safe. I walked away from a lot of things. And that’s why I started Weird and Awesome. That’s why I do Magic Hat and that’s one of the reasons why I think Joketellers Union is here [at the Clock-Out], too. Creative real estate is so important, and we were like, “How can we create a space for the comedy that we think should happen?”
IJEOMA I’m so grateful for people who stuck in there. When we came down to this war of, “Is Seattle comedy going to become this racist, sexist, abusive trashhole or not,” there were some dudes of privilege who were like, “I’m going to get onstage and grandstand and make this about me and how not that I am.” And you didn’t do that. You very quietly kept keeping space. And you very quietly kept holding the relationships that you valued. And you kept quietly reaching out and taking risks on people. That matters a lot, and it’s wonderful to see.
EMMETT You make a decision when there are so many beautiful voices out there that are not getting the time or the volume that the shit voices are. Does another white bearded male have to say this? Or can I create a space where the original voice can say it? I find most comedy—most anything—kind of boring. I want the weird, sort of scary, challenging stuff. That’s why I do the stuff I do. I don’t even like producing shows. But if the shows I want aren’t there, I’ll produce those shows. First I’ll try to trick somebody else into doing it.
Seattle has amazing trans folks and nonbinary folks doing comedy. There are jokes that are being told that have never been told before, because it’s an experience that’s never been talked about. These jokes are being told in places that are safe for them, because this is a population that is under the threat of violence. And that’s very important, but that also means that maybe I’ve got to step back a little. And that’s fine.
Stand-up comedy is one of the best things to see people do bad at, because at least you see a human journey. But when they’re saying, “It’s because I’m not safe here,” that is a huge, huge problem. I have to look at the space I’m creating. Are there wolves that are going to hide through this open-door policy because I am bad at noticing wolves, because I am not afraid of them? And that is hard, and it’s not fun. And all you want to do is just be your beautiful self. And I see you be your beautiful self.
I love that the content you put out is very important conversations about race—and makeup tutorials. [laughs] There was a period two years ago where I stopped being able to get out of bed. And when I started being able to get out of bed, there were a lot of choices. I realized I had to make a real big decision about what I wanted to do on and off the stage. A big thing is that I didn’t want to work with creepos and rapists anymore. I also had to figure out who I was and why I was getting out of bed. And part of it is the way that some of these makeup tutorials are all about being comfortable with who you are and also finding your identity. I would find myself looking at these, which will never—I mean, most of my face is covered…
IJEOMA I’m still pleasantly surprised at the amount of people who never wear makeup and they watch every video. I love makeup because it’s a lot of fun. And it’s a personal celebration. It’s self-expression. It’s art. I’m coloring. We have all these ways in life that we forget that we live first and foremost for ourselves, and that we have to celebrate ourselves.
I did this thing in New York, this panel talking about race and feminism with other Black women. And this woman came up to me afterwards and said, “Oh, I love your makeup. I watch your videos.” And she’s like, “I didn’t know you were a writer.” [laughs]
EMMETT We’re constantly put in boxes. People say, “Well, you’re a writer and an activist, so you can’t do this.” Or, “You’re a comedian, so you can’t say this. Just stick to the comedy. Don’t be political.” We’re constantly told we can only be one thing, and that’s just such a fucking lie, right? I think that’s how people are controlled, through labels. Sometimes it’s very obvious and harmful, like race and gender. But it’s the insidious, tiny things… I intentionally use multiple “ands.” I’ll talk about cats and dogs and turtles—and people will be like, “That’s not how you use language.” I’m like, “You’re not the mayor of my mouth.”
IJEOMA Yeah! [laughs] Horrible movie, by the way.
EMMETT The Mayor of My Mouth.
IJEOMA I’m dying. It’s true, though. I write on race, and one of the great tragedies of writing on social issues is that something can be what you’re called to do, but it doesn’t mean you can make it your life. In fact, you shouldn’t. I’m already so much less fun to be around than I was a decade ago. I make Uber drivers cry. No one can ask me “How’s it going?” without getting a lecture on how horrible the world is because it’s where my brain is most of the time. And unfortunately, part of the problem with oppression is you can’t ignore it. You don’t actually get to spend time on yourself or your community or finding out what else you could be.
Especially for the arts. It’s very easy for people to think that because you’re driven to do something, it’s going to be the thing that always gives you joy. There’s a difference.
EMMETT Oh, the thing you love will break your heart. The scary thing is now we’re in this city where people are struggling to live. People don’t realize that if you want to enjoy cool things and art, things like affordable housing and public transportation are instrumental because all of us [artists] are using the bus. It’s real scary.
IJEOMA Seattle likes to think its art just magically gets done. Like we’re elves in this workshop putting out this art for them. And it terrifies me, especially as a writer, as a Black writer, to see how devastated the arts community of color has been by rising housing costs. Tim Lennon [currently the executive director of LANGSTON] used to help organize these get-togethers of artists. You can’t get people in the same room anymore, because you can’t get people in the same city anymore. It’s just devastating. And I want to create space, but also I really worry about Seattle not appreciating where its art comes from, and understanding that they have to pay for that.
EMMETT Yes. People always complain about, “Remember when Seattle comedy was good?” I’m like, well, you’ve got to show up to it. Being an audience member, it’s political activism.
IJEOMA It’s one of my biggest frustrations with Seattle: There’s a huge amount of wealth in this city that likes to say they live in Seattle for the art and culture, and they don’t want to put a penny toward it. Even just going to Portland, even going to Olympia, people expect to put a little money forth. And here, people will be like “$10, what!?” And you’re like, “Are you kidding me? I know you’re wearing dad jeans, but you have the money.”
EMMETT What did you pay on your Uber [laughs]? What did you pay for coffee today? How much is that IPA? And you think, “Just all I’m asking, spend what you drink in one evening for the whole month on art.” And if everybody did that, if everybody did just spend 40 bucks a month on elevating voices that they believe in, the things they care about, how much louder and [more] beautiful would this town be?
IJEOMA Exactly. If we want our arts to stay vital and diverse—that’s why I get so mad when people complain about paywalls. People will be like, “I would read that article but it says I have to pay 90 cents.” I’m like, “How do you think the writer got paid for that? How do you think that works?”
EMMETT I did a thing the other day where I wrote a real dirty joke, which is a little off-brand for me. But I was very proud of it. And I’m like, I’m never going to say this on stage but someone should hear it. So I posted, “For $2, I will tell you this dirty joke.”
IJEOMA I saw that!
EMMETT You know what? I’ll give it to you for $1 [laughs]. Friend discount. But I got so many messages, like, “Can I hear the joke?” and I’m like, “$2!” And they’re like, “But come on, I’m a huge fan.” And I’m like, “Obviously not.”
IJEOMA It’s so funny the people who want time. In my inbox right now I’ve got this multi-paragraph request from someone who I guess is a fan of my work and wants me to talk them through their own personal conversation that they had with a Black woman that didn’t go well. And I’m just sitting here like A, I wrote a book on this shit. And B, no I’m not going to help you win this thing with a Black woman. [laughs] And it’s so frustrating because, of course, they want this to be free. A lot of times I’ll send back a rate. People get so offended.
The other day someone said, “Hey, is it alright if I put this paragraph you’ve put on Facebook in my blog post?” And I was like, “No problem.” I was surprised that she’d asked. She’s a friend of mine. And then she PayPaled me 50 bucks. She was like, “Hey, this is your work.” If I want someone to read over something, I’m going to send you some money for that, because we know the time and the value and we also know the exploitation in the arts.
Exploitation everywhere is rampant. And if we want to be free from that, we can’t be a part of it. But so many of our audiences who love what we say get so upset when it applies to them.
EMMETT When you build bridges—because you have to build bridges if you want to cross to certain places—sometimes people treat you like a bridge. And I’m like, “No, I am someone who walks across bridges. Please consider walking with me or enabling my walking instead of walking on me.”
IJEOMA Meet me halfway. Comedy is interesting because it’s always been such a microcosm of white male America for me, because it is mostly white males. And part of what I’m working on right now is looking at white male mediocrity and how hard it works to protect itself. And comedy is one of those symbolic ways where you see it trying so hard to say, “We don’t have to make better jokes. We don’t have to learn to be more responsible people. It is our God-given right to get on stage and tell hack jokes and have you laugh.”
And it’s so weird because it’s the antithesis of what they say comedy is, right? You can’t push forth this whole thing where you’re telling your audience, “It’s just a joke. It’s just words,” and then at the same time say, “It’s sacred, it must never be critiqued or we’ll die and cease to be comedy.”
EMMETT When I first started, the attitude was that you were trying to appeal to the common man. And when I first started telling jokes about my marriage and how much I loved being with someone wonderful, people told me, “You can’t talk about how great your wife is. They all want to hear about your shitty wife so they can think about their shitty wives.” And I’m like, “I don’t want to tell jokes to those guys.” I was branded a feminist comedian and all I did was not be shitty about women. That’s how easy it was. Now it’s a little more complicated. You actually have to put your money where your mouth is.
IJEOMA I feel the same way about activism, especially progressive activism. I feel like I have to keep reminding people: It’s called progressive because it progresses. And you get people who are like, ‘‘This is the way we’ve always done it.’’ Like, ‘‘Well, isn’t that a problem?’’
I just spent a week at Harvard Business School and I remembered, ‘‘Oh yeah, I’ve been saying whatever the fuck I need to say for a decade now.” And in other spaces you can’t. It was weird for me to remember that. But there are teenagers coming up who one day will look at what I did as regressive. And I will be outdated.
Freedom and progress look like something I can’t even envision yet. And I think art is very similar—the future of art doesn’t look like anything you see right now. That’s maybe the next five minutes of art. And then you get there and then you can see a little further. You can see a little further, you can see a little further. But we forget that when we are in these progressive forms, that the beauty of it is the process. The beauty of it is the growth. And instead, when we become good at where we’re at, and we get comfortable where we’re at, we want it all to stop. We want to make it into a time capsule. And we don’t understand that we aren’t even there yet.