Molly Lambert on Music Writing, Grantland, the Olympics, and the End of Digital Media

This is a free post from Larry Fitzmaurice's Last Donut of the Night newsletter. Paid subscribers get a paid-only Baker's Dozen every week featuring music I've been listening to and some critical observations around it.

I've always been a big fan of writer Molly Lambert, whose curiosity and voice felt specific to me during digital media's heyday and, in the devastated landscape of it all, now feels like an essential asset for survival. Molly's been up to a lot lately; she was a producer on the excellent John Mulaney Presents: Everybody's in L.A., and soon she's following up her 2022 podcast series HeidiWorld: the Heidi Fleiss Story with JennaWorld, the focus of which she describes as "labor rights through the lens of the porn industry...the porn industry has always been this kind of like canary in the coal mine for media stuff."

As longtime readers know, I love having people on this newsletter who have worked in digital media and have moved on to second/third/etc acts career-wise, especially when I feel they have a specific perspective or sense of wisdom. Molly's always fit that bill to me, and we had a great time chewing the fat last month about all there was, what there is, and how things could possibly be...

Let's start with your origin story as a writer.
I just always loved writing and wanted to do it as a job. I read a lot of old magazines. I definitely wasn't thinking specifically about what kind of writing I wanted to do—I just came into writing when you could do all these different kinds of writing online. I was trying to be a TV writer, and everything else I was doing was a side quest. I was having trouble breaking into TV, so I ended up doing whatever I could get paid to do.

Music writing wasn't my main thing, necessarily, but I love a lot of music writers—Greil Marcus, Ellen Willis, Richard Meltzer, people like that. Music writing always seemed like the fun thing you could do where you could just write about whatever you wanted through the lens of writing about music.

I want to zero in on you saying it's the fun thing you could do, because I feel like one thing I've witnessed over the last 15 years is that music writing is typically an easy entryway for writers who typically go on to write about other things. Why do you think that is?
If you're trying to get into the type of writing where you get to go do stuff and write about it, you have to get hired somewhere. But a lot of the writing I was doing early on was kind of like, "What can I do for free where I don't have to buy something, necessarily?" It was a confluence of coming into into the job world at the time when there were all these websites and music was suddenly available to listen to on platforms, because I'd always been a music fan but there was a point before that where you were limited by how much money you had to spend on records. Then, suddenly, you weren't limited by that anymore. That seemed exciting.

Let's talk more about magazines. I also grew up reading them pretty voraciously, to the point where the most random tidbits from magazines have stayed in my head forever. What are some formative memories reading magazines for you?
I found out Santa Claus wasn't real from a magazine. My parents had Spy Magazine, and they would hide it from from me on a high shelf. I got it and read it, and there was an article that was, like, a big exposé about how Santa Claus isn't real. I was definitely a kid reading magazines that made me feel like, "Oh, this is what adults are like," you know? I read a lot of Esquire's "dubious achievement awards." I was really into the L.A. Weekly. That was one of the first things where I was like, "Wow, L.A. is really cool." People from other places think L.A. is this stupid place for idiots, but this magazine made me feel like there's cool people and culture here.

Did you read George?
[Laughs] No, I did not read George. But I remember when it came out. I definitely kept track of what the new magazines were. I read SPIN pretty religiously. I read Rolling Stone. I also saw Almost Famous at a formative age, which made me be like, "Yeah, that would be fun. I'd like to follow the Allman Brothers on tour or whatever." Obviously, that was without the knowledge that Rolling Stone was really sexist in that era, and I would've never been allowed to be the person who goes and does that. But I had this real belief that things were gonna improve—that other people were going to get to do stuff like that.

Tell me about how you started getting clips, as well as your experience writing for Pitchfork. You started writing there less than a year after I did.
I had started my own website with a friend of mine from college, because I was young and naïve. I was like, "I'll just write a lot of stuff, people will see I can write, and then they'll give me writing jobs." But I definitely did a ton of stuff for free—music writing, TV reviewing. Because I'm an L.A. person, it never occurred to me to submit to real magazines. I was never like, "Oh, I should apply for a job at GQ," because I wasn't in the place where you get those jobs. So when I did start getting hired to do stuff like that, they were like, "Why didn't you just apply and reach out?" I was like, "Well, I just never thought of that." I didn't know you could! I was excited to work at Pitchfork, because at that time it definitely seemed like one of the big things you could do if you wanted to be an online writer.

This is gonna sound like the most naïve thing in the world, but when I started working there, I was like, "Oh wow, they really do only have one woman on the editorial staff." Obviously, the crisis in conscience arrived for the higher-ups eventually, sort of.
Honestly, I also was very naïve. I was shocked every time I was in a situation where I was the only woman, which happened a lot. It's almost like anything interesting, fun, or cool gets coded as, like, male. A lot of the women I knew were doing stuff for women's and beauty magazines, and I was just not interested in that at all—but I understood that that's where the money is for a lot of women writers. I wasn't disparaging people who were doing that—I was just like, "Well, what I'd really like to do is the stuff that guys get to do." The fun, Hunter S. Thompson stuff.

But I definitely was like, "Oh, everybody at Pitchfork is a white guy." It was surprising to me, and it was an interesting time, too, because it was like right when they weren't covering pop music yet. I remember having some arguments about that, being like, "Hey, you guys, if you're gonna cover all these other types of music and not just the white guy indie rock..." Which was, you know, the flagship. Famously, they published the review of the Robyn record that made Robyn kind of popular again, but I was very confused by what the litmus test was for whether something was worthy of Pitchfork.

I remember having an argument at that time about Taylor Swift. "We should review the new Taylor Swift album"—which, I think, was Red at that time. I was like, "Look, if you're gonna be Rolling Stone, which you clearly are gonna be, you gotta cover everything. If your goal is to be the main music publication and not just a neat indie rock publication, then you should cover these big tentpole albums." They're covering, like, rap, but not pop, you know? I was like, "Alright, I mean, you're clearly not just interested in covering pop." The Taylor Swift album merited the same amount of attention as, like, a new Kanye album—because it's important in pop culture in the same way. And they were like, "No."

Then, I think there was an overcorrection. [Laughs] Now, when people talk about the poptimism thing...nobody was ever saying all pop music is good, you know? But it was really this outdated thing, to me. "It's not written by the artists, necessarily. All these people produced it and it comes out of a mixing bowl." Well, yeah, but you could say the same thing about rap and a lot of rock music. Nothing is just made by one person. It was a very old-school Rolling Stone attitude—kind of like, "Unless somebody is a male singer-songwriter, we don't take them seriously." To me, I was like, "All music is the same." If I like music, I'm gonna listen to all the music, you know?

Again, there's very much been an overcorrection, where now a pop song comes out and people are like, "This is the greatest music that's ever been made." I don't necessarily think that, either. But I still think that, even if somebody is just a singer and not as much of a writer, they're still an artist.

I do remember getting in an argument about a Rick Ross album that I thought was bad. I remember saying, "This sucks, you guys are dumb for liking this." I thought I was hired to do that, you know? But even then, I did notice I got assigned a lot of women artists to review. I was kind of like, "Hey, I can review other things, too!"

Let's talk about your time at Grantland, which was where a lot of people came into broader contact with your work.
That was, to me what the internet was was gonna be fun for. What I liked about all those new journalism guys and gals was the [notion] that writing should be fun, and fun to read. Now that there was this ease of access—you don't have to go buy a magazine—my mindset about it was always like, "We're writing stuff for other people to read while they're like trapped at their boring jobs instead of working." Which, to me, I thought was a very worthy goal! That was amazing, and I felt very lucky to be part of it.

I wasn't a sports person, either—so it was funny to be working at ESPN. A lot of guys would be like, "You're living my dream! That's my dream, why are you doing it?" And it was like, "Well, I don't even care about sports, so I'm surprised by that too!" How many guys were like, "Wow, you have a great job, you should give it to me—it should be my job instead of yours"...why would I do that?

How did it feel when Grantland shut down? It's almost a rite of passage for millennial media employees to suffer at least one completely devastating career setback.
I've faced them a bazillion times, honestly.

Word.
It sucked. I really believed the whole time that media was just going to move online, and that if I got in early on the ground floor of online media, then I'd be in a good position for when all the magazines realized they had to go online. I was just surprised at how much all the big brands really dragged their feet for so long—they waited too long, and it was too late. In terms of the money, the ad model for print advertising wasn't adapted to the internet. I thought Grantland was the first of, "Oh, now there's going to be new magazines! The internet's going to make new Esquires and Rolling Stones, and that'll be the vanguard!"

Instead, it turned into this two-tiered system at all the old magazines where it was like, "We'll pay you a reasonable amount of money if it's in print, but if it's online, it's somehow much less money, even though it's the exact same product." That was just kind of crazy to me. and that's still kind of how it is. So what really happened is that the things that go into print are things where they're getting getting access to somebody, so the print stuff gets much more boring because it's just something where there's some kind of money being exchanged, or you're covering an Amazon show and you get access to somebody from an Amazon show, and you have to give it positive coverage because they have to keep their working relationship with Amazon—and that's now what pays the bills.

I do think women's magazines, which have always had this kind of transactional stuff going on behind the scenes...maybe we're more ready to transition to that. But if you wanted to write Hunter S. Thompson stuff—if I just wanted to go to a horse race and write about how weird the people in the town are—that kind of got squashed, and, to me, that's the only interesting thing about magazines.

When I went into celebrity profiling, which is what really started paying my bills after Grantland folded, I was definitely like, "This is not my passion," you know?I'd had such a cool job, so to then have a normal media job definitely felt like—not a step down, but just kind of like, "Okay, well now what am I doing? What am I gonna do next?" Like, I don't want to do this, necessarily, but I also feel like I can't turn this down, because I need money. I just was emailing with someone right now about maybe doing a celebrity profile, because I need money.

I try to do things that I think I can find something interesting in, but I've also done things where I thought it was going to be interesting, and then it really turned into something else in the editing. Once I realized, "This is like advertising"...but, then, it's like, "Well, they should pay us like advertising!" If I'm gonna do something that's essentially an ad for somebody's show, then I should be getting paid more. But, you know, you talk to people who worked in magazines in the '90s, and they will tell you they just spent all the money because they were like, "It'll keep replenishing forever." When you hear about how they spent the money, you're like, "Wow, it seems like you could've avoided this by not, like, buying caviar every day."

There's this Hunter S. Thompson quote from right before he died. He wrote this piece for ESPN.com towards the end of his life, but it made a big impression on me. He was like, "The American empire is over. This will be the first generation of Americans to do worse than their parents."

In the material sense, the whole buying a house, buying a car thing—that's bad. What are your larger thoughts on that sentiment of his?
I think the buying a house thing is a huge part of it! It's like they got rid of all the incentives to work. Why would you work, if not to earn enough to buy a house? The reasons you would give up your life for a career have been taken away—but you're still supposed to give up your life for your career.

After having worked really hard—I was really grinding, up until about the end of Grantland—and then I got really disillusioned and was like, "Maybe I don't want to work that hard anymore." Because it doesn't seem to matter how hard I work. But, you know, I think the real culprit is tech. The problem started with tech buying up these brands and gutting them and destroying whatever people liked about them, and then not replacing it with anything else—which, it seems like it was purposeful to gut journalism.

But, you know, now it's happening in film and TV. Now I'm seeing everybody I know in film and TV freaking out abou how they spent all the money. I really don't know what we're supposed to do.

Me neither. It does seem like everyone I know is kind of like, "I'm just supposed to make money for the rest of my life, but they've made it so hard to make money."
It's impossible. I've seen it in other fields, too. Everything turned into a tech startup. where a company starts, they build up the valuation or whatever, and then they kill the company.

I think about how my mother was a film production accountant. She worked freelance for many years, on different projects, and then after that she got a job at a studio and was an accountant for 20 years. Just the idea of anyone having a job anywhere for 20 years is unthinkable. And so many things were tied to that—you got health insurance. And then they introduced independent contracting, where you don't get health insurance with your job and you have to do whatever the company wants—but the company doesn't have to do anything for you, because you're not a real employee.

I had that experience a couple times, at some name-brand media companies where i was like, "Okay, well, this is the company I thought was going to be stable. This was what I thought was the safe choice." And it's also completely unstable, and they're making me prove myself, and I feel like I've already proved myself a few times—but it also feels like a trick where they're like, "Just prove yourself, and maybe we'll do something for you." But they're clearly not really going to.

I've had that experience many, many times.
I thought these were gonna become the new mega media companies! There was a point where almost everybody I knew was working at a website. Now, I don't know what the plan is.

I don't think anybody does.
I'll tell you who I blame for everything: Ronald Reagan. The boomers were just incredibly lucky, because of the post-war economy. We're more like the Depression babies. The idea that the boomers would just be like, "Everything will be like this forever," that was also just a lie based on a capitalist model of endless growth—that things are just going to grow forever, and everyone's going to make more and more money. Then, Ronald Reagan got rid of all the guardrails for labor protections. Empire is over. We're now in the death rattle.

Have you watched Adam Curtis' The Mayfair Set?
Oh my God, yeah.

I've been watching that lately and I'm like, "Jesus Christ, all of this is happening again right now!"
The idea that there's wealth consolidation—it's like the money isn't even gone, it's just been consolidated to, like, five people. And nobody in charge is gonna do anything about it, for various reasons. I mean, I've never been a workaholic, super-careerist person, so after getting thrown off the horse a few times, I was like, "I need to work less hard and figure out ways to make money, but I can't be stressed about it all the time, because I have no control over it." I got to, like, find ways to just enjoy my life—and, you know, I'm a pretty low-maintenance person in that way. I've tried to treat like periods between work like that, instead of just being stressed out and looking at a computer all day, being like, "Where's the email that's going to give me a job?" I gotta go walk around in the park, eat a little ice cream.

It's funny to hear you describe yourself as somebody who kind of dialed down the work, because I feel like you've always been up to a lot of different projects. You were even a little ahead of the game when it came to working in the medium of podcasting.
Podcasting is also a bubble in its own way, obviously. Moving to podcasting, if you want to do something interesting, you just have to talk about it instead of writing about it—and, as it turns out, talking about it is much easier than writing. I've been trying to make podcasting my main gig.

When I say, "I'm not a careerist," that's probably an exaggeration, because I definitely want to keep writing for a career. I'm trying to keep it going by trying a million different things—but that's sort of by necessity. That's just how it is in the gig economy—you have to be doing, like, 10 things all the time, hoping one of them will pan out. But then I also was like, "Okay, now I haven't been trying hard enough. I need to try harder."

My ambition come back a little bit, I think. My feelings just got hurt, because I love doing this thing—and it doesn't love me back, necessarily. Then you're like, "Maybe I'm an idiot for trying to do something I love as my job. I should've tried to just make money and had my passion on the side." But I've had friends who learned to code and got laid off from their jobs after a few years, so there's nothing you can do that's safe anymore, where you're gonna have that job for 50 years and get get your pension and health insurance from doing it.

So, then I decided to write a long podcast. Because I'd been such an internet person, I'd written a lot of things that felt very ephemeral. So I was like, "Okay, I guess I'm going to try to do something that can have more longevity"—something that isn't just meant to, like, last a day online. If you're lucky, they last longer than that.

Heidiworld came out of a fear of trying to purposely make something more important and serious. I was like, "I'm gonna write a narrative podcast." Also, I saw other people I knew doing stuff like that. My friend Jamie Loftus was doing a lot of really great stuff in the podcasting zone that got me excited about just writing again, so shout out Jamie Loftus. I thought, "She's doing she's doing cool, interesting stuff in the field of podcasting—maybe I could do that too." Outside of just having a show where we talk about TV, maybe I could do something that's novelistic, but as a podcast. I've been sort of afraid to write a book, because you can just picture writing a book and then it's just sitting there, remaindered.

Writing Heidiworld was about the things that I liked about internet writing—the immediacy, the feeling of spontaneity, all the new journalism-y stuff that I loved doing. If I was writing a book, I'd tighten up a little bit, but if I'm writing a podcast, it can get really loose. So that ended up being really fun, and I was definitely also like, "I hope anybody cares about this when I put it out." [Laughs] But you kind of have to just become delusional, because otherwise you'll be like, "Well, all these other things petered out, so like why wouldn't this too?" So that's my new attitude—horse blinders.

That's the only way to do it at this point. Doing something for yourself is so much more rewarding than, like, writing a piece for a publication and sending it out into social media to be like, "Is anyone engaging with this?"
Yes. I got really into, "I have to do this because it's the thing I have to do," which is how I'd always felt. Then, you get kicked in the head a few times, and you're like, "What if I'm wrong?" But, again, it's not on us, especially after COVID. It does feel like planning ahead is a folly. You want to plan ahead, but you really can't. We don't know what's gonna happen, so now I'm just trying to get these podcasts off before the sun burns out.

Were you happy about the reaction to Heidiworld?
Yeah, I was so happy about it. I was writing it by myself for a year with nobody looking at it, so it did feel very much like a thing that existed entirely in my head. I was like, "I hope other people care about it." I'd pitched it to some other podcast companies where they'd been like, "Nobody cares about this." Gen X people were like, "Everybody knows the Heidi Fleiss story," but Gen Z people were like, "Who the fuck is that? we don't know this name at all."

That's crazy to think about, man.
I know! But isn't that interesting? There's things from '90s media that are getting lost. What really made me want to do it was all the OJ Simpson media—there was the documentary at ESPN and the FX show. I grew up right when that was happening, and it had a huge effect on me, seeing how power works in a city like L.A. The Heidi Fleiss scandal and trial, as a kid I was like, "Why is she getting in trouble?" Why is it illegal to sell sex? Shouldn't you be allowed to sell your own body—the one thing you own in this country? Also, if she's getting in trouble, why are all the rich men who bought sex from her not getting in trouble? Why is it just her?

Working on it really reinvigorated my love of writing. I felt like, "This is what I should be doing right now." It came out and people liked it, but my Irish Catholic and Jewish attitude towards things is to expect failure, and then you'll be pleasantly surprised if anything else happens.

Tell me about working on Everybody's in L.A.
It came up super randomly. John asked me if I wanted to come on the show to book some of the non-comedian guests and pre-interview them for the live interview segments. It was extremely confusing what I was going to be doing, and then I was like, "Oh yeah, I know how to do this." It was the most incredible thing I've ever gotten to be part of. It was so fun, and it felt like a culmination of all the things I had been doing where I was like, "I hope people like and get what we're trying to do." Even as things are bad, if you make something good and cool and it finds the right audience, nothing is better.

Going back to what you were talking about before regarding your early career ambitions, it seems to be a nice full-circle moment for you when it comes to working in TV. I mean, I know that "TV" doesn't mean what it necessarily used to be—but, it was TV!
It was TV. I was also giving up on ever getting to work in TV. You know, things are not super stable in TV now, either. It was really satisfying to be like, "Wow, I got to work on something cool with the coolest people, and whatever else happens, I got to do this." That rules.

I feel like that's a much healthier lens through which to view one's career than how we were trained to think about working in these industries, where it's, "OK, I'm gonna do this, and hopefully that'll mean that I can do this, and then I can move on to doing this, and then..."
Yeah, well, art and commerce are not always best friends. If you want to make art and get it out to an audience, you kind of need commerce, and it's hard to manage both of those things. Money just makes it so hard, too. But when something comes up...I do feel like Everybody's in L.A. was such a miraculous thing to even exist. I felt so lucky, and it did make me be like, "Wow, I've been really lucky."

I've had a really great career, actually, for somebody who's outrunning the collapse of everything. If anything, I've been unable to appreciate all the stuff I've been a part of, because I was so focused on, "Well, what now? What next?" This was the first thing where I was like, "I'm just gonna appreciate that I get to do this and feel excited every day I get to come work on this show and hang out with these people. Don't think ahead—just enjoy it, just be here now.

It had been so long since I'd been on a team working with other people where we were all working towards a common goal. I haven't had an office job since Grantland. I love being on a team with people—I love the rapport, and just talking. It's like being on a bench at a baseball game with your teammates. It's great to share things with other people—I'm not at all like, "Me, me, me." I'd rather be on a team with people where we're all working on things together.

One thing that stood out to me about Everybody's in L.A. was John's bit about the Olympics coming to the city, which I recall you being quite outspoken about a few years back when the bid was going through. Talk to me more about your feelings regarding that.
I mean, it sucks, frankly. The thing about L.A. is that we have a little group of elected officials in this huge city, and they make a lot of decisions that are not good for all the people in the huge city. It's always been a corrupt place. It's never had a good mayor. It's never had progressive people in charge doing the stuff that we need. The Olympics obviously exacerbate all these problems, and I think people have been seeing that more since the Rio Olympics. It feels like people are more aware of the fact that the Olympics are basically a grift.

My grandmother was a German Jew who was going to be in the 1936 Olympics. She was basically kept on retainer by Germany to be a token Jew in case everybody in the world would boycott the Olympics. Instead, they just were Hitler's Olympics. She didn't get to compete as a high jumper, but she did get to, you know, escape Germany. It's pretty easy to trace a line from that to my fixations.