Rebecca Jennings: We need more pop stars with strong opinions about the Internet
Vox's Senior Correspondent on ice skating, frenemies, Chappell Roan, and Having It All. Plus, a preview of her forthcoming novel, "Mutuals".
Before Moodeng was Brat, and bro-podcasters ruled supreme, the Internet was actually a pretty fun place.
Things were still weird of course. Videos like ‘My anus is bleeding’ and ‘trogdor the burninator’ were peak comedy. Crazy Frog’s cover of the Beverly Hills Cop theme song went to number one in most of Europe. Everyone was six degrees from Kevin Bacon. But it didn’t really matter.
In the 2000s, the things you watched and read, the communities you subscribed to, did not necessarily define you as a person. The internet felt mostly inconsequential. It wasn’t that serious.
Now it is.
Which is why we need people like Rebecca Jennings writing about it. As Vox’s senior correspondent, Rebecca understands the Internet and its influence better than most. Be it Mike Tyson’s bout with Logan Paul, the conspiracy theory that Spotify was pushing Sabrina Carpenter, or the “soul-sucking labour” of promoting yourself online, her reporting is nothing short of essential reading, on par with other HP favourites like , Amanda Mull, and .
Having admired Rebecca’s work from afar, I was thrilled when she agreed to a short interview.
Our edited and condensed conversation touched on her early days in Vermont, destination weddings, Chappell Roan bashing Billboard, the Joan Didion-ification of Martha Stewart, her forthcoming novel, the future of media, and more.
It’s a somewhat unserious conversation about serious topics. In other words, one of my new favourites.
ES: I love your top. Respectfully, it’s giving Snuggie a little bit.
RJ: Laughs. Thank you so much. It has fur cuffs and a fur hood. I was influenced to buy it. Amelia Dimoldenberg wore it in a TikTok two years ago.
ES: It’s fun.
RJ: I’m going skating today, I think it’s appropriate.
ES: Is that outside? Indoors?
RJ: It’s a media event for Bryant Park Winter Village. I love the cold and skating was my entire life growing up, so this is very exciting for me.
ES: Really? What years are we talking about?
RJ: From ages three to 18. I did competitive figure skating, and theatre on ice which is the coolest sport in the world. It should be in the Olympics. It never will be, but it’s awesome.
I also played hockey and I worked at the rink, so my life was ice.
ES: This is so Canada-coded.
RJ: Well I grew up an hour from the border.
ES: Upstate New York?
RJ: Burlington, Vermont.
ES: Oh shit. What was that like?
RJ: It was great. I love Vermont. It was beautiful and cold. I love going back even though my parents don’t live there anymore. It’s one of those places that’s heavily romanticized. I’m sure you know this being from Vancouver, but it’s a place people love to vacation to.
It’s funny you mention the Canada of it all because we used to hate the Quebecois so much. They would come to Vermont and not tip and shop at Abercrombie & Fitch and wear the most egregious cologne. You could spot a family of them from a mile away… And it’s sad because I absolutely love Quebec. I’m having my bachelorette party in Montreal. I'm excited to go, but there’s a playful frenemy nature to the Vermont-Quebec relationship.
ES: That’s a great way to describe it. What are you doing in Montreal for your bachelorette?
RJ: I’m not totally sure. It’s in a couple of months. My maid of honour and I are figuring out where we should stay, and what to do… I’m hoping to see Sami the drag queen. She went viral a couple of months ago for this video where she dressed up like the MAGA version of Quebec. She was like “My pronouns are Quebec.” It’s really funny. She’s absurd and surreal. We timed the trip so we could see her monthly show.
ES: I just got married this summer and we didn’t have a wedding party. Was that a conversation for you and your fiance? Or was it a no-brainer?
RJ: I’m only doing a maid of honour. I have a sister, who I was maid of honour for, and a best friend, and I wanted them to have a part in the wedding. We’re also having a friend officiate but I didn’t like the idea of having ten of my “best” girlfriends up there. I feel like it’s a little exclusionary, I’d feel weird about leaving people out, or including people who might be too polite to say no.
We’re also not going to have anyone up there with us during the ceremony, I think. It feels a bit young to me. Maybe if I was 23, and my social circle was smaller, but I have a lot of friends and I don’t want to impose a hierarchy.
ES: Did I see on Twitter that you’re getting married in Scotland?
RJ: Yeah!
ES: Please explain.
RJ: Laughs.
ES: Actually, let me rephrase that. Did Scotland hold any special significance to you and your partner before you decided to get married there?
RJ: Yeah, so I’ve been to Scotland three times. I loved it so much. Edinburgh is one of my favourite cities in the world…
We have been to other cities in Europe. We went to Italy and Croatia together and we considered both, but we were worried the language barrier might make wedding planning tricky. And a lot of the venues were outside the city. With Scotland, that’s less of an issue…
We found this incredible venue and most of our guests will be able to stay on-site for two days. It’ll be a big trip with everyone we love. It’s going to be such a blast.
ES: I probably should have asked you earlier but do you like being interviewed? Or would you rather be the one asking the questions?
RJ: I get more nervous about interviewing other people because I don’t want them to think I’m a complete idiot.
ES: That’s tea.
RJ: Like, if I’m being interviewed, I sorta feel like that’s your fault. You thought I’m smart? I’m a fucking idiot. Laughs. The pressure is more on the interviewer than on the interviewee.
ES: Right. So you’re saying the stakes have never been higher.
RJ: Laughs. Surprise, bitch.
ES: Have you done any interviews lately that were particularly nerve-wracking?
RJ: It’s usually whenever I know things are going to get contentious. When I know I’m going to have to ask uncomfortable questions. I’ve interviewed a lot of influencers and whenever I ask about money it can be a little, you know…
I think influencers especially are used to having control over anything that comes out about them. And so when they don’t have that control, when they’re speaking with a journalist, they tend to panic or feel like they’re being attacked, when I’m just doing my job.
ES: Yeah, the idea of control is something that comes up a lot, especially when you’re interviewing younger people who have spent their entire lives controlling their own image. I feel like a lot of people don’t understand the expectations that journalists might be bringing to a conversation.
Not totally related but I even think of Chappell Roan getting mad at Billboard for reporting that she has split with her management team. Like, c’mon. This is basic stuff. I love her, I’m usually on her side, but that seemed like an overreaction.
Most celebrities live in a fundamentally different world than you or I…
RJ: I think there’s a fundamental misunderstanding of what a journalist’s job is, especially because, right now, there’s so much discourse around how the media landscape is changing. Politicians and celebrities go on these press tours, and they speak with podcasters and influencers who ask very friendly questions. It’s an avenue for these celebrities and politicians to get their message across, and to seem relatable to their audience. And so when this class of people is confronted with a professional journalist, they think “This must be the opp.” No, this is me gathering straight-up facts.
I have to remind myself that most celebrities live in a fundamentally different world than you or I. They live in a world that encourages them to be less curious, and more isolated from normal human interaction. And it also encourages them to be paranoid. I can only imagine what it’s like to have that much attention and pressure, to have other people’s finances resting on your shoulders. That must be extremely difficult. And I think modern fame is unethical in many ways. But it seems that unfairness is thrust back on people who are just doing their jobs.
You see these viral clips of celebrities talking to journalists on press junkets, doing promo for a movie or something. The celebrity is not excited to be there and their fans will say “Yes! You are not a dancing monkey.” But the journalists don’t necessarily want to be there either, sitting around, asking the same fucking questions. Guess who’s getting paid a lot more? Laughs. It pisses me off so much. Not that I’m completely pro-journalist. Journalists are very annoying.
ES: Thank you for acknowledging the elephant in the room.
RJ: I’m so brave. But, yeah, celebrities are also annoying and they get paid so much more to do the same stupid stuff we do.
ES: Bristling over basic business reporting also plays into larger concerns surrounding anti-intellectualism, and media literacy. I was thinking about this while watching the Martha Stewart documentary, which I mostly enjoyed. I found it so odd that Martha was the only person interviewed on camera. I have to assume it’s because she had final cut and could control the narrative. [Editor’s note: I was wrong! She didn’t have final cut. She has even come out criticizing parts of the film.]
RJ: I interviewed Martha once. That woman is such a professional. The way she can snap into character. She can speak directly to the camera without breaking contact, which, if you’ve tried, you know, is extremely difficult. She speaks perfectly, she never has to retake. It’s incredible to watch.
ES: Let me be clear: while I have my criticisms of the documentary, I think Martha is one of the best to ever do it. I hope she reads this and reaches out. It feels like she’s in the same rarefied air as Joan Didion in a way.
RJ: You might be the first person to ever make that comparison. Please say more.
ES: I’m completely riffing but it feels like they’re both the archetype, no? Extremely well-put-together, elegant women, who are idolized by younger generations. I dunno, maybe I’m in a bubble, but it feels like both Martha and Joan’s stocks have never been higher. The Martha documentary in particular feels like a victory lap.
But, yeah, basically they are both smart, talented, beautiful women. It’s a sweet spot for a certain type of person. Myself included.
RJ: That’s the thing that tends to go unspoken. Many people like Joan Didion because she looks really cool in those pictures from the 70s.
I was chatting about her recently with someone, and I forget the minutiae of what we were saying, but it essentially boiled down to the idea that Didion was fundamentally a conservative figure and how one of her most famous pieces centers on the idea that hippy youths are fucking idiots... Like, Slouching Towards Bethlehem is very funny and holds up in a lot of ways, but it is notable how she and Martha operated in the realm of conservative domesticity while still being proto-girl bosses…
I have always identified as a lazy person. It’s why I’m a professional writer.
ES: Didion even has that quote that gets shared every few months about using the good silver every day, because every day is all there is. There’s definitely a domestic element to her that is idolized, I think. But again, I’m just spitballing.
RJ: We will always be fascinated by women who straddle the boundary between traditional domestic lives and hugely successful careers.
ES: It’s really about having it all.
RJ: We should bring back the Having It All discourse. Very 2004.
ES: 1985 to 2004, when Tina Fey finally broke through the glass ceiling.
RJ: Honestly, when I think about Having It All, she’s the number one thing that comes to mind.
ES: Speaking of which, are you writing a novel?
RJ: I sure am. I’ve been writing it for almost four years, and I’ve been working with my lovely agents since about 2022. We’re getting ready to submit to publishers in January.
ES: Exciting.
RJ: I’m excited and nervous. As everyone knows, the book process takes forever. It started as a COVID project and it’s been the most fun, rewarding experience ever. I’ve always loved writing fiction, but it took me until the pandemic to realize I had an idea that I wanted to do in novel form.
ES: What is the idea?
RJ: So it’s called Mutuals.
ES: Great name.
RJ: It’s about these two kids that meet online when they are 11 and they connect over a messaging platform. They both want to be influencers and the story follows them as they grow up. One of them becomes famous and the other becomes someone who manages influencers, and they eventually reconnect in person. It’s basically a story about how we make connections in a world where connections are financialized and extracted by tech platforms.
ES: Four years is a long time. How did you balance writing with your work life?
RJ: I have always identified as a lazy person. It’s why I’m a professional writer. It’s the only thing I like to do. And so the real motivation behind the book was that I was having fun writing it. I wouldn’t have been able to do it if I wasn’t enjoying it. I would wake up early, write a bit, and then also do it after work. It was such a joy to do. I know that’s annoying, but it’s true.
Also, I took a novel workshop with Catapult, which is now defunct. It was a 12-week program, and we had this great teacher. I kept meeting with the other four women in my group even after it concluded. Every month for the past three years we have workshopped each other’s fiction. It’s amazing motivation.
ES: Who are some of your influences when it comes to fiction?
RJ: In fiction, you always have to come up with a comparable title, something that came out in the last couple of years that sold well that you can base your premise on. If you liked X you might enjoy Y. My comp is Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin. I think it’s incredible. It also follows the lives of these two kids into adulthood, though that’s sort of where the similarities end.
I would also be lying if I said I was not influenced by David Foster Wallace, who is one of my favourite writers. I’ve read Infinite Jest twice. It means so much to me in this horrible way. It’s similar to mine in that it takes place in this near-future dystopia. And it’s about “What is the value of life and love?” Those are questions that are never going to go away.
Also, there’s this documentary called Jawline… It’s basically about these aspiring teen boy influencers and how they get swallowed by the industry, and then discarded when they’re no longer valuable on the platform of the moment.
ES: I haven’t spent time with any of those. Where should I start with David Foster Wallace?
RJ: Don’t start with Infinite Jest. I would start with some of his magazine essays. “Shipping Out” is great. People have different opinions about him. He probably was shitty as a person but you know what, separate the art from the artist.
ES: I mean you’re talking to a Matty Healy apologist so I get it.
RJ: Oh my god. I saw them last November. It was one of the best concerts I’ve ever been to. I love that band.
ES: They’re the best.
RJ: I also defend Matty. It has not always made me popular online.
ES: It’s like trying to boil the ocean.
RJ: We need more pop stars with strong opinions about Internet culture. As much as I think Chappell Roan’s music is fun, it’s not always quite for me, but I appreciate how she and some of our younger stars are talking about the Internet because they grew up on it. Even though he’s older, I think Matty Healy is interested in the same questions I’m interested in.
ES: I was thinking about him last week during the whole conversation about bro podcasts. I mean, the whole last tour was centered on male loneliness and how that can feed into the male media ecosystem. It was in front of us this whole time!
RJ: I think having men raise the alarm about that is powerful. Women have talked about how toxic these spaces can be forever, but it feels like that perspective can be dismissed as shrill, or like we’re being overly sensitive about sexism. To have someone famous like Matty, or Hasan Piker talking about it is different. In Hassan’s case, here is this insanely hot, big, strong dude saying it’s wack.
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ES: Given how much you think about influencers and social media and the internet, I wonder what you think about Taylor Lorenz’s idea around journalists capitalizing on the attention economy. How do you see younger journalists carving out a career for themselves at this point?
RJ: I was actually talking about this just last night. In our newsrooms, it feels like reporters are often assigned stories that, historically, might have fallen to new grads. People fresh out of school. Where are the early-20s, and mid-20s journalists who are eager to prove themselves? Those jobs don’t exist anymore. It’s sad.
The jobs that existed when I was coming up in the mid-2010s, which were funded by venture capital, offered a chance to be part of a newsroom. Now it feels like they are, if not completely gone, then at least heavily diminished. And so I admire the younger folks who are taking their talents to Substack, TikTok, and Instagram.
The problem, though, is that you don’t necessarily get the same checks and balances that a newsroom provides. You don’t always get to have a gut check with someone who’s been working in this for ten years. I knew nothing when I first started. I needed mentors and editors who understood how this stuff worked, and who could guide me to produce something worth reading. While I admire a lot of those people, I wish we could bring some of that entrepreneurial spirit into existing newsrooms so that both sides could learn from each other. I think Taylor is so good at bridging that divide. She’s an incredible reporter, but she’s also meeting audiences where they’re at by making content that speaks to them. She goes viral and reaches more people than a typical news article.
I’ve been trying to figure all of this out for myself. Right now my plan is to start posting more. And I hate that the answer is to give these billionaires more money, but I don’t know how to get around that… If I want my work to be read I need to change strategies… Sometimes it feels as though simply having a job isn’t enough anymore. You have to have a second job promoting yourself in order to get the theoretical next job, or to get a large enough audience that you can quit entirely and make it on your own. I’m impressed by anyone who does that. I think it’s so cool, but obviously, by its nature, that cannot work for everybody. Not everyone can be a big star.
ES: Not everyone can be Martha Stewart.
RJ: Not everyone can be Martha Stewart. This world where you're famous or you're nothing is very unpleasant to me. This is also a theme of my novel, which will hopefully be in stores sometime in 2026. Laughs.
Rebecca Jennings is a senior correspondent covering social platforms and the creator economy for Vox. She lives in New York City.