It’s around about one in the afternoon on a warm-but-not-hot early summer Tuesday and Luke O’Neil and I are having coffee at an outdoor table in Harvard Square in right about the same spot that “good” Will Hunting sat explaining to his lovely British girlfriend, Skylar, about how in spite of his working class roots he’s actually wicked smaht and I’ve gone and embarrassed my conversation partner. Our table happened, randomly enough, to be located next to a couple of business types who it just so happens own a local bar that O’Neil worked at and got fired from. That’s not REALLY the embarrassing part, but there’s more on that later. O’Neil has spent years as the frontman of Boston-area bands like Good North and more recently No Hope/No Harm but is undoubtedly best known for his work as a predominantly freelance writer – “I guess somehow I’ve become like this notable freelancer, which, there’s a distinction between being a notable writer and a notable freelancer. It’s not that my work is that great, but it’s the fact that I’m freelancing,“ he notes, tongue firmly embedded in cheek – who’s been featured in places The Boston Globe and Esquire the Boston Phoenix (R.I.P.) and Huffington Post.
O’Neil’s been doing his own newsletter, Welcome To Hell World: Weekly Dispatches From The Pit Of Despair, for the better part of the last year. It’s must-read fare that’s equal parts horrifying and heart-warming and disturbingly humorous and soul-crushing and at times optimistic. All that work has culminated in the pending arrival of O’Neil’s first book, Welcome To Hell World: Dispatches From The American Dystopia, and, subsequently, in his getting to talk to schlubs like me not about things like labor disputes or immigration policy or the abhorrent state of the health care or criminal justice systems in his country, but about his own work. And that, as it turns out, makes O’Neil a little uncomfortable. “I’m embarrassed talking about it this much with you. Please make it clear that I find talking about myself to be weird. And I almost get embarrassed to say what I do, like when I went to talk to those guys over there and they said “hey, what are you up to?” a normal thing would be to say “oh, I’ve got a book coming out.” But I don’t say that…“
Writing a book wasn’t entirely part of the original plan; or at least not the type of book that Welcome To Hell World eventually became. But let’s rewind the tape to the beginning. O’Neil was born in the late ’70’s and grew up in Kingston, Massachusetts, the small coastal town that’s about an hour south of Boston and an hour east of Providence, meaning he was equidistant to two vital underground music scenes at a pivotal time. After formative concert-going experiences involving Weird Al Yankovic and Rage Against The Machine – no, not on the same bill but can you imagine? – O’Neil had the opportunity to dive into two thriving underground music scenes at a vital time, as bands like Letters To Cleo and Dinosaur Jr. were blowing up. “(I would see them) and I would learn about all the bands that were opening for them. It becomes like a chain reaction – you go see a band and you find out who’s opening for them, and then you go see that band later and find out who’s opening for them, and I always really loved that about music,” O’Neil explains.
After Kingston came a trip an hour west of Boston to Worcester’s College of the Holy Cross and, following that, a stint in New York City inspired by a love for writing fiction. “I wanted to write fiction,” O’Neil remembers. “I wrote essays in fiction in college and won some stupid school awards, and that’s how I got my real first job. My real first job was I worked for Conde Nast. I moved to New York City – this was around 2000 – and magazines were just starting to have websites. Somehow, I don’t know how, I got a job just on the fact that I was a pretty good writer. I went and applied and interviewed for a normal job to be an editorial assistant and I somehow got it.”
A couple years in New York were followed by a return to the Commonwealth of Massachusetts, specifically to an MFA program at Boston’s Emerson College, a degree that somehow, O’Neil never quite finished. Instead, he got a regular, paying gig at what was then called The Weekly Dig, a free, Boston-based alternative weekly newspaper, back in the waning days of those still being relatively viable thing. “I did two years at Emerson toward an MFA, and I somehow got the job at the Dig, and was like, “well, fuck it, I’m a professional writer now, I don’t need to finish this.” He continues: “I just had to do one more thing to write and defend my thesis. And I had it written, I don’t know why the fuck I didn’t do it. I just said “I don’t want to do it anymore.” And I started playing in my first band, and I thought I was hot shit. I was going to be a rock star! … I just kind of chafed against this program at Emerson, but I guess chafing against structure and discipline has always been a throughline for me…”
That chafing against structure and discipline would eventually lead to O’Neil getting fired by the Dig. As he tells it, in spite of the comparatively liberal office culture in place at the Dig, it wasn’t a fit for his personality in the long run. “Even at a place like that,” he explains, “I just didn’t like going to sit there all day and just being at a computer because the boss wanted you to be in the office.” O’Neil’s run at the Dig was followed by an editing job at free daily newspaper, The Metro (if you’ve ever taken an MBTA bus, it’s the one that’s usually open-faced on the empty seat next to you. This one would prove to be an even shorter run. “I went in the first day, and I remember everyone was so excited that there was pizza in the breakroom, and I just laughed and said “I don’t want to work at a place where people are excited that there’s pizza.” So I went back to waiting tables and freelancing when I could.”
Waiting tables and freelancing eventually lead to O’Neil’s former editor at the Dig, Joe Keohane, getting back in tough about a new opportunity a half-dozen years ago, this time on the pages of Esquire Magazine. “That obviously was a pretty big step for my career and I did lots of great work there, but then I sort of got fired, sort of quit from there? I still don’t really know.” It seems O’Neil’s penchant for what I think Oprah calls “speaking truth to power” but what essentially boils down to calling people on their respective shit had bit him in his own ass. This, you see, is a bit of a recurring theme in O’Neil’s writing career. “I tend to quit or get fired from almost everything I’ve ever done, because I have a very low tolerance for doing things just because that’s the way they’re done. I’m not afraid to speak up – I guess I’m just an impetuous teenage shit still!” As a freelancer writer, editors and websites and print publications (lol) will bring you on board because your words are hopefully going to generate eyes on their pages, sell ad space and/or subscriptions, etc. And if you’re generating content – and clicks – by pointing your spears at the power structure or class imbalance or whatever, that’s a good thing. But when you start to point those spears at the people you’re writing for, well, bad things happen. “I just started talking shit sometimes about how bad the (Esquire) site was getting while I was working there, and obviously the bosses didn’t like that, and we just sort of ghosted each other in a weird way.” O’Neil explains.
Though no longer at Esquire, O’Neil continued having his pieces picked up for publication in a variety of outlets like the Washington Post and the theoretically liberal bastion hometown newspaper that is the Boston Globe. In fact, a quick search on the Globe’s own website produces 364 results as of today. That changed earlier this year, however, in a rather notorious way, after the paper chose to pull a published O’Neil editorial amid fierce conservative backlash (O’Neil had opined – again tongue in cheek – that one of his regrets in life was not “seasoning” conservative pundit Bill Kristol’s salmon when waiting on him at a restaurant years prior). Rather than support their long-time contributor, they caved to pressure from the right-hand side of the aisle that doesn’t need to look hard to find myriad reasons to hate them anyway and instead, as O’Neil describes it, “slit (his) throat.”
And so while starting a newsletter a year ago maybe wasn’t O’Neil’s idea from the start, it has given him a regular, unfiltered, seemingly stream-of-consciousness outlet to provide his unique blend of social and political and personal commentary. “In order to be one of the people now who keeps a job, who have to by your very nature be kind of a boot-licker or a fucking cop,” O’Neil opines. “I think that’s the problem with – and I hate the term mainstream media – but when you talk about the (Washington) Post or the (New York) Times or any New York magazine, in order to stay within the business and climb the ladder and get jobs and keep jobs, you definitely have to be willing to swallow a lot more shit than I certainly am willing to.” It also allows him to address issues like police brutality or throat-punching Nazis or the border crisis or people dying due to lack of affordable health care in a way that doesn’t have to address “both sides” of an issue in order to placate audiences or bosses. “A lot of times, I’ll talk to somebody who can’t pay their hospital bills,” he explains. “The journalistic thing to do is that you’re supposed to call the insurance company to get their side of it. It’s like, “fuck you, I don’t care what your side of it is. I KNOW what your side of it is. Your side of it is that you’re fucking this person over.” It’s pointless to me to ask. It’s like, if the cops shoot somebody, it’s pointless to call the cops and ask why they shot them. They’re going to lie to you…I feel like there’s too much of that now. There’s a lot of interviewing of the alt-right and neo-Nazis and stuff where they’re like “I’m going to show this guy’s words, and they’re going to seem so absurd that everyone’s going to laugh at him!” But I’m not interested in that.”
All of that brings us back to the Hell World book, which is due out next month through O/R Books. Much of it is comprised of pieces that’ve appeared in the Hell World newsletter, with a few companion pieces that appeared in other publications but seemed to fit the theme of the book, as well as a few new essays. It’s largely unedited from it’s original, unique format, which will probably please fans of O’Neil’s work and frustrate or confuse other people. “I think the book might be interesting and weird. I’ve certainly never read anything like it, which can be a bad thing. I can imagine people thinking it sucks, and maybe it does, I don’t know. But it’s like a weird mix of reporting on labor and health care nightmares and police violence and also commentary on other people’s reporting on that and also really a memoir of my own struggles with mental health and physical issues” he explains.“I think it’s a weird book, and it’s either going to be weird and people will really like it, or really weird and people will think “this is garbage.” All of that is just fine with the author, himself.