Ryan O’Connell, 31, is a writer from Ventura, an unpretentious beach town north of L.A. and south of Santa Barbara. It’s the type of place travel blogs call “under-the-radar.” O’Connell and his personal life hardly follow suit. He’s built a career writing about himself online, beginning with a post-college, pill-popping stint in New York during which he became a primary voice on Thought Catalog, the once legendary online confessional for millennials he helped build. In his personal essays, he pondered “real-life” questions for people still wondering if they’d ever be capable of having fully functioning adult lives.
But that was earlier this decade. Since then, O’Connell quit abusing pharmaceuticals, moved back to L.A. and began lending his sharp sense of humor and relentless trolling of pop culture to other characters as a Hollywood screenwriter. In the meantime, he also wrote his first book, I’m Special: And Other Lies We Tell Ourselves, a memoir about navigating his young life, particularly in terms of being a gay man living with cerebral palsy. Amid developing I’m Special as a digital series, O’Connell landed a coveted spot writing on the new season of Will & Grace, which returns to NBC next Thursday.
Yesterday morning, O’Connell and I got on the phone to talk about how Karen Walker helped him realize he was gay; how he and his fellow writers rebooted Walker and the show’s other characters a decade after they first bid TV farewell; and the perils of selling a sitcom that includes one guy shitting on another guy’s dick.
Were you a fan of Will & Grace during its original run?
Like any self-respecting, closeted homosexual, Will & Grace was my guiding light. When I was 13 or 14, it’s not like I knew what a gay sensibility was. You’re just drawn to certain things, and you don’t know why. I remember watching an episode and being introduced to Karen Walker for the first time and being like, “Oh my God, whoever this woman is, I’m so drawn to her humor and her rhythm.” Even her voice. And now I’m like, “Yeah, that’s a gay sensibility.”
I remember reading this message board Television Without Pity that was all TV recaps. In one episode of Popular, an old teen comedy that Ryan Murphy wrote and I was obsessed with, someone had got kicked off the football team, and a commenter wrote, “Who cares? The only people that watch this show are gay men and women.” I remember being 12 and thinking, Yeah, and me! Eventually, I was like, “Oh…” Characters like the women in Popular and Karen Walker helped me find my campy, gay-as-fuck voice.
Why do you think it deserves a reboot?
People think TV is so gay now, but I have a huge issue with that. It’s not. Network television is still predominantly straight. There may be more gay men as part of ensemble casts, but they’re like the appetizers, sliders or bruschetta, never the delicious main courses. Will & Grace is still fairly radical even today, just in the fact that it features two gay men and two women. There’s still not a lot of thorough representations of gay men on TV, except Looking, which nobody looked at.
There’s speculation about how well the world of the show will play to audiences today. Is that something you talked about in the writer’s room, in terms of shaping the show’s voice?
That happened pretty organically. I think it feels updated because these characters are living in 2017 and we know what this moment is. At the same time, we know their voices. We know their rhythms. We didn’t reinvent these characters; they are who they are. They’re going to be lol-tastic, and hopefully, people will enjoy it.
How did you get into TV writing?
I always wanted to be a TV writer. I remember in college, I had a writing partner and we would write a spec script every summer. We wrote a spec script for Gossip Girl, lol. When my writing partner and I broke up, I didn’t do any screenwriting for a while. I knew the traditional ways of getting into the business — being a writer’s assistant and all that stuff — but because of things like the car accident I got into when I was younger and being disabled, I didn’t think that path was accessible to me. Typing 60 words per minute was never going to be my journey. I had this idea that if I built a platform online, it might help me get an agent and all the rest.
The first show you got staffed on was MTV’s Awkward, right?
The Awkward job was weird. I remember living in New York and waking up one morning, devilishly hungover, and thinking, I need to watch that show because I feel like I’m going to write for it one day. That thought came out of nowhere, but that weekend I watched the first two seasons and loved it. Then, on that Tuesday, an episode from the third season aired and in it, a character name-drops me as her favorite blogger. I was like, “Holy shit, this is insane.”
Smash cut, I wrote a pilot that was hot garbage but got an agent and decided to move to L.A. I didn’t know anything about the entertainment business. I moved here in July, right after staffing season ended, but I met with my agent and told him how much I loved Awkward, and he was like, “Perfect because they’re staffing right now.” I met with the showrunner and got staffed within my first month of living here, which is unheard of. This is the kind of story I want to tell from behind bulletproof glass, because it doesn’t usually happen that way.
You experienced rejection later on, though.
Definitely. I think it was really good for me. Rejection and failure are humbling and a good reminder of how hard it is to achieve what you want. I paid my dues later, trust me.
How so?
When Awkward ended, my career was on a weird high. My book had just come out, and it was optioned by Jim Parson’s production company. I had my dream team assembled to go out and pitch it. But we pitched it to all these networks, all of whom passed. It was devastating. People weren’t ready for this disabled jelly. As forward thinking as Hollywood is these days, at least compared to 10 years ago, people are still like, “Oh, your show doesn’t star Kevin James? This isn’t another stay-at-home dad thing?”
To be fair, I pitched the show I wanted to make. In the first episode, someone shits on a guy’s dick during anal sex. Not just the tip, but full penetration. So it’s sort of like, “Jeez, why didn’t anybody buy this?” but at the same time, I know why.
Eventually, after not selling for a while, it found a home on a digital platform within Warner Brothers, so miraculously it’s still limping along. During that process, I didn’t work for a year. Instead, I tried to write and sell another book that nobody bought. So I definitely learned a lot. It was like throwing spaghetti against the wall and seeing what stuck.
Then, because life is so insane, I got offered two jobs in the same week: I wrote for Daytime Divas on VH1, starring Vanessa Williams, and then I wrote a teen movie for Dreamworks. I went from having nothing to work on to having a lot to work on, which was great and how I prefer to work.
You don’t like pouring yourself into one project?
Sometimes I wish there was more space between them, but I’m always working on two things. Even now, I’m doing Will & Grace as I finish up the scripts for I’m Special. I haven’t had a weekend that hasn’t involved some work in forever. But I like that because I genuinely love writing, and as I’ve realized over the last couple months, I truly don’t have any hobbies. Like I even still write on Tumblr.
I wanted to ask you about that. You still blog often, and you have a VICE column. It doesn’t seem to me that there are many successful screenwriters and TV writers who still write as much about their personal lives as you do, especially off Twitter.
I think you’re fucking right. When I stopped writing for Thought Catalog full-time, I was over-sharing so much about my life for like $2 a day, that I was like, “Fuck this.” But I quickly realized that I love sharing these sort of personal stories. And doing so when you don’t have to feels even better. When I blog these days, I’m not getting paid. That’s just for me. And with VICE, it’s not like I’m telling those stories for the money either. They’re just stories I want to share, so it feels very pure and honest. There’s something liberating about writing you want to get out. I’ll always do it. Creatively, I have a lot of itches that need to be scratched at all times. And when you’re writing TV or movies, you’re always dealing with notes from the studio. So it feels good to have spaces that are just for you.
Tierney Finster
Tierney Finster is a journalist, screenwriter, actor and model from Los Angeles, California. She is a contributing writer at MEL, specializing in love, sex, mental health, drugs, queer culture and the cannabis industry. She has written for publications such as Playboy, Purple, Dazed and Confused, Jezebel and Broadly and was the key researcher behind Sex On, HBO’s revival of its iconoclastic docu-series Real Sex.
