The Pursuit of Joy with Tom Jackson
Words by Luccas Hallow
[Note: This interview is featured in issue 001 of The OK Times]
Talking to Tom Jackson, co-founder of GAYLETTER magazine, Supergay Spirits, and creative director at the advertising agency Mother, was an oddly reflective experience. Tom and his creative partner Abi Benitez have progressed leaps and bounds in the last decade, taking GAYLETTER from a NY-based newsletter to the forefront of the queer publishing industry in a short span of time. Their cover stories with the likes of Frank Ocean, Marc Jacobs, Janelle Monae, and many others are some of the most interesting pieces I read all year. This is, in part, due to the care and precision that goes into each issue of the magazine from all parties, and partly due to the colossal figures being discussed.
But, I would be remiss if I didn’t give proper acknowledgment to the creative input of Tom Jackson himself. His interview with Frank Ocean continues to be one of my favorite published works in recent years, especially considering Ocean rarely gives interviews anymore.
So, yes, going into this interview, I was incredibly self-aware
about not coming off as a blithering fanboy.
What kept the conversation going and grounded, upon reflection, is the fact that Tom has incredible experience. His career is incredibly varied and covers multiple disciplines. Between interviewing some of the most interesting and influential people in modern popular culture and creating a platform for underrepresented voices, there is no shortage of intriguing stories. A pleasure of this job is being able to hear those stories directly from the source and share in something greater than just two people talking. Hearing how Tom interviewed Spike Jonze or how
GAYLETTER came to be are both fantastic stories. I believe
it to be a service that I was able to hear them from the source
and then, through laborious editing and self-doubt, share
them with you.
I like to talk to everyone about inspiration. So, for you, I want to know what the inspirations for starting Supergay Spirits and GAYLETTER were?
I think they both came about from friendship and partnership. GAYLETTER started in 2009 with my best friend, Abi. We were going out a lot at the time. We couldn’t find an interesting guide to parties that were happening. So, we’re hanging out one night, and we decided to create one—which was a bold, irrational decision. We started doing an email newsletter every week with the five things you should do that weekend [or] the five parties [you should go to]—just fun things to do. And then that quickly took off.
We got nominated for a Paper Magazine Nightlife Award for Best Party Blog (There weren’t really that many party blogs, though). So we were nominated, and we won. And then someone from the New York Times was at that event and they saw us win, so they asked us to be in this article that they were doing about new nightlife people in New York. We thought it was just a little piece, but it turned out to be a cover story for the Style section—which was a pretty big spotlight—and that really blew up what we did [in a good way]. [Eventually], we built a website, and then we turned it into a magazine a couple years later. So, we’ve been doing that ever since.
Supergay [Spirits] started because I was good friends with the owners of the wine shop across the street from me. They were two guys [with] really great taste, and I just loved going in there, looking at their products, and hanging out. One time, Aaron, one of the guys, asked if I was interested in developing this idea. He eventually shut down the store, and we started it. We’ve been working on it for the last two years. The inspiration behind both of these projects is to do something fun and to do something to add a little joy and a little light to the world and share our passions and points of view.
It’s just always interesting hearing the roots of things. To hear that the goal for you was making something to share joy—that isn’t something I’ve heard before, at least not in the same way. So, that’s interesting to me.
Well, they both have required a lot of work to get them out into the world. To birth them into the world is a really, really crazy steep learning curve. Figuring out how to publish a magazine and then making a spirits brand is a very, very complicated process. So, there’s a lot of stress and hard work—a lot—involved in the background. But, ultimately, they both were created to bring a little more joy and fun into the world and to share the things that we’re passionate about.
And so, for you, creating these two businesses in dominantly cisgender, heterosexual fields, the kind of representation that GAYLETTER and Supergay are offering is really valuable. Granted, most fields are dominated by straight, white men. But, is that something that you were thinking of when you were making them? Or is it something that stands out to you in the process of building the brands?
It’s something that definitely stands out. [I don’t know] if it’s something we thought about initially. We just really liked the ideas, and they sort of felt fresh and exciting. No one had done [either of] them before—what we wanted to do, I mean. There are and have been many other queer publications before GAYLETTER. But as the years have gone by, we’ve noticed that there’s not that many people in the publishing space who do queer publications anymore. I mean, it’s really small. Really small. And so, yeah, we’re definitely aware of that and [conscious of] how we can play a part and be a positive contributor to that world, how we can continue the legacies of people like Bob Mizer and Butt Magazine.
And then liquor’s a very hetero industry, like super hetero, even though the people who are serving drinks at bars and restaurants are, in a higher proportion, queer people...There’s queer bars—not [in] all places, but there’s a tradition of nightlife and parties and clubs and bars in the queer community. Gay people love to drink and queer people love to drink. And queer people work in hospitality. So, it was almost like there was no brand that was trying to tap into that world and contribute to that world. A lot of the bigger brands put a rainbow on their bottle. But, nobody’s really done it authentically. The intention wasn’t to be only a gay brand. It was to make an incredibly good quality spirit. We liked the fun and the joy that the name had, the freedom it allowed us in creating a design for the label, and the opportunity to have a presence in social media and the world that is also full of joy. It gives us the permission that maybe some other brands don’t allow themselves to have, because they’re so in that small-batch, Prohibition era craft world.
Maybe it’s just me, because I am a big whiskey drinker and an advertising student, but I pay attention to spirit ads, especially being 21. And the ads for them, especially whiskey, are really macho and sort of chauvinistic. So, that’s why I’m thinking there has to be a purpose to naming your spirit brand like that, since everything around it is so diametric.
Yeah, and I work in advertising as well. That’s another career I have. A while back I worked at an agency, and I helped launch a tequila brand for a very famous musician who is in a family boy band, (that will probably narrow it down for you.) This pop star partnered with an older fashion designer to make tequila, and I helped develop that brand and their first advertising campaign. I worked super hard to help develop a visual world and identity that felt fresh and original, but the design of their bottle and their taste levels were so generic. They basically decided to follow a path that has already been set by George Clooney and Randy Gerber with Casamigos, you know? There was nothing unique about how they saw their brand in the world...They partnered with a very large company who makes a very famous vodka. And it was a lesson in how these huge companies work and how they
spend their money and what they do with it. And it was frustrating trying to get them to do something different, but also it was a lesson in what not to do when launching a spirits brand.
Well, I also feel like branding and advertising for spirits is just so copy and paste. It almost seems like everything’s kind of made with a template. And to see the way that you went about your branding, as an advertising student and as somebody who’s looking for those kinds of things, it just stood out to me so much. I was looking at the website for Bulleit Bourbon last week for a project I’m working on, and it’s so much the opposite of intuitive. So I don’t know if there’s a question lying in there, but I really enjoyed the branding that you did for your product.
I appreciate that. I mean, we wanted it to be as simple as possible. And to avoid a lot of those obvious cliches that a lot of these brands do. I’m familiar with [the templates, because] I looked at a lot of those sites and a lot of those brands. They follow a template, and we just didn’t want to do that. Because, you know, we’re a new brand for one, so how are we ever going to compete with some of these big, big companies by following the same template? Like, what’s the point? If you’re going to do something new, you might as well do something that feels truly new. Make it memorable, as much as possible—in name and design and everything. That’s how I look at it.
So, what is the goal with Supergay? You don’t have to get into too much detail, but what is the expansion of the brand and what do you hope to accomplish going forward?
I mean, we want to continue to grow the brand and grow into other states because, right now, we’re only in New York and New Jersey. So, we’d love to grow, because people write to us all the time and ask us if they can get it in their [area]. People in Miami, people in California [ask] all the time—someone wrote to me from London, too. That would be amazing. And then, we have ideas all the time for things we’d like to do in terms of other products and other iterations of [the brand]. But, I’ll save those for another time.
Since you started off as a spirit company, what is your experience with cocktails, liquor, mixed drinks, etc.? Is there some sort of deep rooted love for the mixed drink that made this something you wanted to do? I know that not everything has some huge thing behind it, but I like to deal with inspiration and purpose a lot in these interviews.
Well, I’ve always loved drinking. I’ve always enjoyed the world of it, too. With GAYLETTER and that world, we went out a lot and we were always at parties, always going to events. I always loved having a cocktail and having a good time. Alcohol; it’s a great, true social lubricant. And I’ve had some of my best times out drinking vodka and so, for us, it was the simplest spirit there is. It used to be legally classified as tasteless and odorless, so it wasn’t allowed to have a smell or taste. That’s obviously changed and people are allowed to make vodkas that are a little more interesting now, which is what we tried to make. [We wanted to make] a vodka that has a lot of complexity to it, but is one of the cleanest spirits out there. We liked the simplicity of it and that it can be mixed in so many different ways. Because there’s not many out there that you can actually sip, we wanted to make a vodka that was great mixed but enjoyable enough to drink on its own. So, that was very exciting. And that took a really long time of recipe development, but we’re really happy with the final product because people genuinely really love it and enjoy it even on its own or on the rocks without needing to mix it with something—which is like a true compliment to the product.
To pivot elsewhere—when I was doing my research, I read that you studied film and contemporary art, which stuck out in my head for a couple reasons. My initial reason for being hired at Off-Kilter was to do film critiques, because I can’t think about anything in just the simplest, broadest terms. That’s sort of why most of my questions are like, well, what was the reason behind this? I have a very analytical way of thinking about things. One of the things I absolutely love is just to talk about film with anyone who will talk to me. So I was just wondering, even though it’s not expressly what you do, what’s your film background? What made you want to study it? What’s the heart of that for you?
I always loved it. I have loved movies ever since I was a kid. And I used to make movies, like home movies, with my sister. We would make these little sketches. So yeah, from that I went and studied film at university with a minor in acting, and I just love it because I got to watch movies for school. That’s just so much better than regular high school. And then I always kind of wanted to work in film in some sense. I worked with this girl at this shop, and she was like, you want to make films, you want to work in production? You should study advertising, because you basically get to make commercials and you’re like the writer and creator. And so, I did. I went back to school for another three years to study advertising and really thought of that course as a way to get into production in some way. But yeah, I love movies, and I love studying and learning about all the different areas.
So, like you said, there’s so many different areas of cinema—what is your favorite? I know that’s broad, but I don’t want to put any qualifiers on something as expansive as cinema.
In college, I loved 1970s American cinema and 1980s/90s Australian cinema and directors like Peter Weir, Phillip Noyce, and Jane Campion. I loved Jane’s short films. I loved “Picnic at Hanging Rock.” I loved the sparse, reflective vibe of that era of Australian cinema. And then I was really into 90s indie American cinema. I loved Kevin Smith’s “Clerks” and “Pulp Fiction”—really anything by Robert Rodriguez. I loved all the work in the film “Four Rooms” that Rodriguez and Tarantino and two other directors did where they each filmed a short film in one room of a hotel. There’s one section [in that movie] based on this Roald Dahl short story, “Man From The South,” that I’d read in high school, and I was obsessed with. I thought it was one of the best short stories ever written. It’s about a rich man who offers another man a bet to light his lighter ten times in a row at a resort in Jamaica. If he does it properly, he will give him his brand new car. If he can’t, he has to chop off his pinky finger. That’s a divergence from what I was saying, but yeah, I loved the 90s indie movie scene in America. The genre that I disliked the most in college was when we had one whole semester on pre-Weimar German cinema. It was all black and white and silent and my class was at 9AM on a Thursday morning, so I would just always fall asleep every week. What period or genre is your favorite?
I’m definitely with you on 90s independent cinema. The whole rise of Sundance is probably one of my favorite periods of film history, just because it’s so varied and there’s so many moving parts to it. But...somehow this always comes up in my conversations, and I feel like a broken record saying this, but—David Lynch. He’s like my whole reason for why I am writing about film. Absolutely love him.
Interesting. I’ve tried to love David Lynch, but I don’t. I don’t know. I’ve tried. I mean, I watched “Twin Peaks” when it came out. Like, I remember I was a little kid, and I remember being fascinated by it. But, I remember seeing Mulholland Drive and being like, What?! I was angry at the end of it. I remember being angry. I was like, What the fuck was that? Why would they do [something] so emotionally turbulent? I kind of hated it. So, I’m fascinated when people like David Lynch. Maybe I need to revisit him.
Oh, I won’t disagree that he has elements that will totally turn you off from the jump. But, I was a really interior-minded kid and so much of my time was intensely maladaptive daydreaming during class. So the first time I saw “Eraserhead,” it was like fireworks for me.
You connected with it.
Yeah, I mean, the surrealism of it and just the complete oddity and dedication to buying into your own bullshit is like David Lynch’s whole philosophy. The whole idea of him being like, I just had a dream, and I made a movie out of it, and that’s Mulholland Drive. That’s fascinating to me.
I actually learned how to meditate at the David Lynch Transcendental Meditation Center, since he’s one of the biggest TM practitioners and patrons of that field. I loved it. It was one of the most helpful things I ever learned how to do—learning how to meditate. And so, I think he’s a cool guy. I need to spend more time with his films.
So did I, yeah! It’s amazing. But okay, I can’t talk about David Lynch in every interview I do.
It’s your trademark! One day, you’ll interview David Lynch, and it will all make sense.
God I wish. It would just be an hour and a half of me asking about “Inland Empire,” because I’m one of five people who like that movie. Anyway—
Well, ya know... I had a chance to interview my favorite director, which I didn’t mention earlier. But when I was younger, my favorite director was Spike Jonze. “Being John Malkovich” was a transformative experience. I thought, you can make a film like this? That is so ridiculous. And it was funny, but just so clever. And I had the chance to interview him a couple years ago for an Australian magazine that my friend worked at, and she just asked if I would interview him. And it was the weirdest experience, because the magazine wanted to do this 10 things I’ve learned angle. It was on a press junket for his movie “Her.” And so, I had my half an hour, and I walk in and I said to him, "okay, they want to do this 10 things thing." I was wearing a “Kids” T-shirt—the Harmony Korine movie—and he stopped me and was like, “Oh my God, I love your T-shirt. Let me send it to Harmony.” And he took a photo of me and sent it to Harmony. And I was like, Oh my god, this is surreal. And then I told him about the 10 things [angle], and he goes, "I don’t want to do that." I’m like, Oh, fuck, because all my questions were like, what did you learn about this? What did you learn about that? And he goes, "I just want to have a conversation. What’s your name? Tom? Yeah, I just want Tom and Spike to have a conversation." I was like, All right, cool. So, I basically just asked him everything I’d ever wanted to know about him and his work. And, you know, it was just like an advice session. It was really handy. I really learned a lot. So, hopefully, you’ll get to have that one day with David Lynch.
