When all is said and done, Rob Harvilla will make at least 120 episodes of his podcast 60 Songs That Explain The ’90s. As you might’ve guessed from the title, this was not the plan. Rob’s show is my favorite music podcast in the world, and its willingness to veer outside its own bounds is one of the great things about it. The idea, at least as far as I can tell, was to use individual and iconic songs — the first three episodes were on Alanis Morissette’s “You Oughta Know,” the Gin Blossoms’ “Hey Jealousy,” and the Wu-Tang Clan’s “C.R.E.A.M.” — to explore what was going on during this particular decade. But Rob’s explanations are never just explanations, and the show became another thing.

I’ve known Rob Harvilla for a very long time — not quite since the ’90s, but pretty close. Many years ago, Rob was both my boss and my friend at the Village Voice, an august institution that was mid-death rattle when both of us joined the staff. (We’re both tall.) We were like Tim Duncan and David Robinson up in that newsroom. Rob has worked for a bunch of other publications in the years since — he was my editor when I was writing about action movies for Deadspin — and his podcast, part of the Ringer’s extended universe, has taken him to beautiful new places.

On every episode of 60 Songs, Rob does get into the cultural context that led to certain songs getting so scratched into our souls. He tells those stories with more grace and warmth and empathy and enthusiasm than most critics can’t even approach. But Rob also gets into his own personal history, and he deprecates the motherfuck out of himself. He’s funny. A bit about Rob’s time bagging groceries — “look what he’s doing to your quiche” — made my laugh so hard that I thought I might barf.

Rob’s writing voice works beautifully in podcast form because it was always conversational. At the end of every episode, Rob has a conversation about the song in question with someone else. I was on the “Ice Ice Baby” episode, and Courtney Love used the “Smells Like Teen Spirit” episode to sing some unpublished and unused lyrics that Kurt Cobain wrote for the song. But the real attraction is hearing Rob talk about these songs, turning them into springboards for him to talk about himself.

Rob’s podcast is now a book. Tomorrow, Rob will publish 60 Songs That Explain The ’90s, a book that’s about way more than 60 songs. Since Rob writes every episode, the transition from podcast to book is clean. But the book isn’t Rob’s podcast episodes written out. Instead, he uses basic themes of the ’90s — things like the idea of selling out — and uses them to make unexpected connections. Rob’s been one of my favorite music writers for many years, and it’s a treat to read him going full widescreen.

With Rob’s book coming out tomorrow, I did a quick email interview with him. (It would’ve been longer, but we both kept fucking up and forgetting to check our email.) Rob and I share a publisher, so we’re technically labelmates or whatever, but that doesn’t have anything to do with me running this interview. I’m not getting points on his book or anything. We’re doing this for the love — like it was still the ’90s.

First off: Why the ’90s? It’s the time when we both had our formative experiences, but is there something else about the decade that feels totemic? Or is it just a personal thing?

ROB HARVILLA: Yeah, I started off insisting that the ’90s were totemic + distinct + culturally unparalleled etc. etc., and I can still convincingly make that argument if you need me to, but really it’s entirely personal. I grew up in the ’90s. I went to high school and college in the ’90s. That’s it; that’s enough. My one-line justification for all this is: The music you loved as a teenager is the most intense and most resonant love affair you’ll ever have in your life. Doesn’t matter if you grew up in the ’90s, the ’30s, the 2010s: You’ll (happily!) chase that adolescent high for the rest of your life, even if the song you loved most back then was Whale’s “Hobo Humpin Slobo Babe.” (Please let me embed this YouTube in a Stereogum article; it’ll be the thrill of my professional life.)

The braces! Love her braces. I do think the ’90s hangs together better as a decade, an ethos, a lifestyle, and a coherent musical footprint versus, say, the ’00s or 2010s. Maybe that’s because it’s the last decade not dominated by the internet, before Napster atomized the music industry, before The Monoculture ceased to exist if it ever really existed at all. Modern rock radio right now is still dominated by Nirvana, Pearl Jam, Green Day, Alice In Chains, and on and on — you’d think that rock ‘n’ roll died in 1994, and maybe you’d be right! But no, no, really: I was a kid, and this is the music I loved, and that’s all the justification I’ll ever need even if I pretend otherwise.

You’ve covered artists — Prince, Daft Punk, Eminem, even Britney — who I don’t really think of as ’90s types, even if they did have big and important songs that came out during the decade. How do you think about these artists in relation to the decade? How many times have you looked at songs from 1989 or 2000 and really wished that you could fold them into the semi-arbitrary construct of the strictly-defined ’90s?

ROB HARVILLA: Dude, I hate 1989 so much. I hate it for keeping Faith No More’s “Epic” from me, and also Janet Jackson’s Rhythm Nation 1814, and the Cure’s Disintegration, and De La Soul’s 3 Feet High And Rising. But I’ve made my peace with it, and I genuinely love talking about artists who did their best / biggest work earlier — Prince put out, like, 65 albums in the ’90s, and I listened to and loved all of them, and then spent the entire Prince episode talking about his assless VMAs outfit instead — and I love talking about the artists who did their biggest / best work afterward, too. I tried to talk myself out of Eminem for a long time, because for sure he doesn’t feel ’90s really at all, but there’s no denying he was the jump scare in the end credits of the ’90s. But I especially dig the distinction between the new stars embraced by the ’90s and the established stars who found themselves grappling with the ’90s, even struggling a bit: your U2s, your Madonnas. Plus I learned to love Janet’s Velvet Rope every bit as much as I love Rhythm Nation, so it worked out alright in the end.

As someone who’s about the same age as you, lots of the ’90s songs that I tend to love the most are the random half-remembered deep-cut bangers like Ruth Ruth’s “Uninvited” or Silkk The Shocker’s “It Ain’t My Fault.” I’m pretty sure you’re the same way. The songs that you cover in the book and on the podcast encompass some really crazy and diverse terrain, but most of the stuff you cover is pretty canonical in one way or another. Does it hurt to look at your spreadsheet and be like, “Damn, I don’t know if I’ll get to work ‘Flagpole Sitta’ in there”?

ROB HARVILLA: Oh man I love “Uninvited,” truly. And I was thrilled whenever it came on the radio, and that’s a perfect example of a song I loved (truly), but at 14 years old I could not justify spending $16.99 on the Ruth Ruth CD. Superdrag! “Sucked Out”! The next Superdrag album after “Sucked Out” (Head Trip In Every Key!) that was somehow even better! Underrated classics and half-remembered deep-cut bangers are crucial to this enterprise, absolutely, and do I try and honor them amidst all the “Wonderwall” and “Juicy” and “Black Hole Sun” discourse. But oh wow yes looking at these spreadsheets hurts every time: The podcast jumped from 60 songs to 90 to 120 because I just could not bear not to talk about, like, “Whoomp! (There It Is),” y’know? And I’m still going to leave so much rad shit on the table. I’d love to do a Superdrag episode, and it hurts me that I (probably!) won’t.

I did the adaptation thing with my column, and the worst case of writer’s block that I’ve ever had was when I sat down to put together the proposal. But you actually write out your podcast episodes, and I love how you’ve kept the same voice from your writing, your show, and now your book. Your voice comes through in all these different forms, and you can still always tell that it’s you. How much of a headfuck was it to adapt a podcast into book form?

ROB HARVILLA: Yeah, the podcast is scripted down to the word — I thought by now I’d be able to “wing it,” but no, no, absolutely not — and consequently I had like 550,000 words of raw material to work with. Which is a good problem to have, but still a huge problem! The greater challenge for me was making these songs make sense together: Can I start a chapter with Céline Dion and end it with Erykah Badu? Does Coolio represent the joys + perils of “selling out” every bit as much as Green Day does? How well do Biggie and Kurt Cobain and Selena and Britney Spears harmonize together? Is the Third Eye Blind guy the decade’s greatest villain, or is Fred Durst too much for him? My hope, anyway, is that the chaos and randomness of it all only underscores how much I still love all of these people; all of this is a little ridiculous, but I mean it, you know? If these songs have nothing else in common, they’re all 10s to me.

60 Songs That Explain The ’90s is out 11/14 via Hachette Books.