Chelsea Devantez and the Book Club
Some guests give you a good interview. Chelsea Devantez gives you a blueprint. Over the course of this conversation, the Emmy nominated writer, comedian, director, and actor walks through fifteen years of doing the work, the cruise ship improv, the web series shot with a manual in one hand, the late night packet that changed everything, and somehow makes it feel less like a highlight reel and more like permission. Permission to start before you're ready, to make something nobody asked for, and to believe your story is worth telling.
If you only know Chelsea from the February trade announcement about her overall deal with 20th Century Fox, this episode is the rest of the iceberg. Here's what stuck with us.
Chelsea grew up all over the Southwest, often without a TV, so her sense of what was even possible as a career came down to one thing, the movies she did get to see. Performing was the only job she could picture. Be Julia Roberts, basically. And it took her years to discover that writing, directing, and everything else were on the table too. Her theater teacher saw it before she did. She snuck a look at the college recommendation letter he wrote and found a line that infuriated her at the time, that she didn't know it yet but she was going to be a director. She fought that prediction hard. Then she got to Chicago, web series were exploding, and she found herself holding a little shitty Canon in one hand and the manual in the other. She was directing the whole time. She just didn't have the language for it yet. As she puts it, it took her a long time to realize how much she loved it.
Before Hollywood, there was the cruise ship, a Second City touring gig she describes as the most amazing thing she would never, ever, ever do again. The Twilight Zone of it, same route, same circles. The genuinely disturbing labor hierarchy that tracked race and nationality. And yes, the dollar bottles of wine and quarter beers. But the craft takeaway was real. Performing five times a week for wildly different audiences, not the performer heavy rooms of Chicago but all of America, is where she became, in her words, bulletproof as an improviser. She learned to read a room and bend a performance to whoever was in front of her. Those 25 cent beers really do a lot, she adds.
Here's the part anyone trying to break in should tattoo somewhere visible. Chelsea didn't have connections or money. What Chicago did have was the late night packet system, submissions where you write a pile of jokes for free and hope someone reads it. Sometimes the email addresses were left open, so you could submit without representation or an invitation. By the time the right packet came through, her writing had gotten really, really great. Jon Stewart read it and hired her for her very first job. The show never aired, the technology wasn't ready for the premise, but she gave it everything, even moving to New Jersey and sleeping on the floor of a barely an apartment to be closer to the work. Years later, off in LA doing her own thing, her phone rang. Stewart was building his Apple show and she was the first person he called to be head writer. Her reaction captures the whole push and pull of confidence in this business. A part of her was very ready for the job, she says, and another part was sure it was the craziest phone call, a wrong number, who's this.
Chelsea wanted to be the one comedian without a podcast. What changed her mind was that she'd always secretly loved celebrity memoirs, a genre everyone writes off as trashy, which she experienced as little Bibles full of successful women being radically honest. On a girls' trip, drunk in a hot tub reading Jessica Simpson's Open Book, she thought, people have to know how good this is. She posted a few passages to her Instagram story. Within 24 hours, people were demanding a podcast. The catch was that she couldn't talk about these books authentically without talking about her own life, and she'd built her career on fiction precisely so she wouldn't have to. The pandemic, a lot of therapy, and one good friend named Kenzie got her over the line. It's become one of the most precious things in her life.
Chelsea is a Scriptnotes superfan, shoutout to Duane's decade old thumb drives, and the conversation lands on a philosophy both she and the host share. The people worth learning from are the ones who share the craft instead of hoarding it. Her go to example is Bianca Del Rio handing competitors the tools to beat her on Drag Race, not out of recklessness, but because she's so solid in her own work that someone else shining can't diminish her. The flip side, Chelsea argues, is diagnostic. If you feel the urge to hoard, that's the sign you don't yet feel whole in what you do. And in a business this toxic, more people getting in only makes it less toxic.
After years of filming TV sizzles and pitch materials with huge stakes attached, many of which went nowhere, heartbreakingly, Chelsea realized she hadn't made anything purely for herself in a long time. An idea hit in an instant, the divine muse kind, and instead of asking what it was for, she just made it. She wrote the three minute short in a night, filmed it two weeks later, finished editing three weeks after that, all on her own timeline. Then came the festival chaos. She applied everywhere, like community college and Harvard, got into a smaller festival, and two hours later South by Southwest emailed to say she was in. She'd already promised the premiere elsewhere and had no idea you were supposed to call SXSW first. The short went on to play every festival imaginable and eventually became a feature. The lesson she finds almost annoying is that after a decade of strategic, goal loaded projects, the one made purely for love is the one that took off. And keep it to three minutes, she says, because when you tell people it's only three minutes, almost everyone watches.
This is the part Duane begged her to bore us with, and it's the most important section in the episode. As head writer on Stewart's last show, Chelsea reengineered how writers get hired, and it went viral for good reason. She made it self submission only, no packets from agents or managers, so unrepped talent knew their work would actually be read and valued. She cut it to one page, because long packets quietly filter for people who don't have to work a second job, and shrinking it leveled the field. She dropped the required formatting, since the specialized late night formatting reads like a foreign language to outsiders and favors people who already had a friend on the inside. She made it topical and ran it over a holiday weekend, because a slow news cycle forces you to actually be funny. And she made the reads blind, names removed.
She half joked about her fear of unmasking seven Harvard Lampoon guys and having to run through a plate of glass. The result was 2,400 submissions, every one read. The room that came out of it looks exactly like America looks like, every region, every class, every gender, and most of the hires had little or no prior TV experience. One writer was working in a factory in Indiana. An exec at 20th was so impressed by a packet Chelsea passed along that she helped him land an agent and a staff job, much of it done over Zoom. That same exec's instinct to lift up deserving writers is exactly why Chelsea trusted 20th with her overall deal. She walked into those meetings leading with her values, including how she wants to hire and what an environmentally forward set looks like, on the theory that you should never hire her unless you like it.
A few rapid fire gems round things out. On pitching, she loves performing and making the art and hates the sales part, the part where she has to convince someone her work is worthy. The relief of her own projects is that they're simply done. Thumbs up or thumbs down, but no more selling. On outlining, she's a whiteboard person, not a story clock person. Know the formulas cold, then don't let them harm you. Chaos first, structure second. On ghosts, she believes in energy, not Casper falling in love with Christina Ricci. On imposter syndrome, it's crippling in her personal life and basically absent at work, because comedy laughs are tangible. You can't tell her she's not good, she says, because she's seen it happen.
For anyone walking into a writers' room green and terrified, Chelsea's advice is almost suspiciously simple. Say one banger thing a day. Just one killer joke or pitch. That alone puts you on track to move up. Beyond that, study relentlessly before you arrive, and get great at writing jokes, because it's rare enough that it'll almost always find you work.
When asked what she's most proud of, she doesn't point to the deal or the credits. She points to that very first web series, the unbeaten, unjaded magic of starting out, and most of all the community of women she built early. They've walked the whole career alongside her, blazing their own paths, and kept her whole, sane, and good. You can get so ruined, so bitter, so sad, she says, but if you have a community, it's the most beautiful thing you can have.
For the record, a few lightning round notes. Home is New Mexico, a place she describes as having an intensely spiritual energy you can't find anywhere else. The order is Tomasita's, cheese enchiladas, Christmas. The comfort food is Taco Bell potato tacos, and there are no notes.
More about Chelsea Devantez:
https://www.chelsearosedevantez.com
Follow Chelsea Devantez on Instagram:
https://www.instagram.com/chelseadevantez
Tomasito’s - Santa Fe
The Smith Society Podcast: This is the Smith Society, a podcast about storytellers and storytelling.
Host: Duane Fernandez
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