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‘60 Songs That Explain the ’90s’: ‘Reality Bites,’ Lisa Loeb, and a Perfect Soundtrack Moment

Rob talks about the great “Stay (I Missed You)” with help from actor and podcaster Rider Strong

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Grunge. Wu-Tang Clan. Radiohead. “Wonderwall.” The music of the ’90s was as exciting as it was diverse. But what does it say about the era—and why does it still matter? 60 Songs That Explain the ’90s is back for 30 more episodes to try to answer those questions. Join Ringer music writer and ’90s survivor Rob Harvilla as he treks through the soundtrack of his youth, one song (and embarrassing anecdote) at a time. Follow and listen for free on Spotify. In Episode 80 of 60 Songs That Explain the ’90s—yep, you read that right—we’re exploring Lisa Loeb’s “Stay (I Missed You)” with help from actor and podcaster Rider Strong.

One super-annoying thing about watching movies on streaming services now is that they try to stop you from watching the credits, right? Within, like, five seconds, they try to kick you to another movie real quick. I rewatched Reality Bites on Peacock—the not-exactly-first-tier NBC streaming service Peacock—and right after Lisa Loeb finished just that line, like 15 seconds into this song, Peacock tries to punt me to a 2020 rom-com called My Best Friend’s Bouquet. I haven’t seen that movie either, I got no opinion on it one way or the other, but, like, don’t interrupt me while I’m listening to this song.

Matter of fact, I dicked around for so long we’re just getting right to it again. The most compelling thing to me, lately, about the song “Stay (I Missed You)” by Lisa Loeb—that’s “Stay,” parenthesis, “I Missed You” close parenthesis—is how oddly it’s structured. There is no chorus, as such, or there are multiple parts of this song that could plausibly be called the chorus. But even lyrically, the verbal structure, the syntax of this song, is beguilingly odd. “You say / I talk so all the time / So.” Why does that work, that series of words? Have you ever thought about how clumsy this series of words should be, at least on paper?

“I’m only hearing negative / No no no bad.” And it fits perfectly, in this song, musically and, uh, syntactically. That part perfectly ramps us up to one possible argument for the chorus. For a song this fundamentally soothing and dulcet and barbed-but-sweet, there’s something very pleasantly off-kilter about what Lisa Loeb sings, and how she sings it. If I promised to give you $100 if you got it exactly right, I’m guessing you could still not recite, from memory, the exact series of words she’s about to sing here, but I am guessing that you could recite it from memory emotionally.

Lisa Loeb was born in Maryland but raised mostly in Dallas; in 1990, she graduates with a degree in comparative literature from Brown University up in Providence, Rhode Island, the gilded armpit of New England, where she also forms an acoustic singer-songwriter duo with her friend Elizabeth Mitchell. They call themselves Liz and Lisa. They get quite popular on campus. Liz sang lead vocals more often than Lisa, but here’s Lisa singing lead on a song from 1989 called “Bowls and Fishes.”

That’s funny. They graduate from Brown. They keep at it for a while but eventually Liz and Lisa cordially split up; Elizabeth Mitchell, in fact, goes on to co-found the New York City indie-rock band Ida. Lisa Loeb, meanwhile, has also moved to New York City, and constructs her own spotlight, and then steps into it.

Here we got Lisa Loeb on her first solo release, The Purple Tape, from 1992. Cassette-only. She sold it at shows. A little more polished than a plain old demo, but still bone-simple, just vocals and guitar. Near as I can tell the actual cassette tape is not purple, just the cover. Which is too bad, but I hasten to add that this is three years before Raekwon’s Purple Tape. Ya best protect ya neck. This is the first song on The Purple Tape. It’s called “Snow Day.”

The reissued CD and streaming version of The Purple Tape includes a lengthy and quite charming interview with Lisa, and she talks a lot about wanting to be perceived back then as a singer-songwriter, not a folk singer. She worried any woman with an acoustic guitar was immediately pigeonholed as a folk singer. She wanted to be known as a singer-songwriter. Down the line that’d give her more freedom to push her sound more toward rock, alt-rock, whatever. She could form a rock or an alt-rock band. The stylistic freedom of being a singer-songwriter was important to her; the songwriter part was especially important to her. As for the songs she was writing, they weren’t raw and totally transparent diary entries, but they weren’t exactly oblique, either. Listening to this song “Snow Day,” you already know what a snow day feels like. You remember what a snow day feels like.

I will be honest and say that at first, I found The Purple Tape to be unnervingly not abstract. If you even set foot on a college campus in the 1990s—if you have any open mic night experience, collegiate or otherwise, as a participant or as an audience member or as like a hostage—The Purple Tape will take you back there. Lisa’s clear, bright, buoyant, mournful voice; Lisa’s clear, bright, deft, and crystalline acoustic guitar. Election Day, right: My polling place was a student-union-type building in a tiny university in my town. There’s classrooms, meeting rooms, whatever, but also a coffee shop right in the front, tons of collegiate-ass college students milling about with their laptops, two baristas clinking bottles, grinding beans, spraying foam. And as I’m standing in line to vote, I’m not listening to Lisa Loeb at this exact moment, but I’ve got The Purple Tape in my head, milling with all this visceral coffee-shop ambiance, and suddenly, bam, I’m back in college. I’m transported. Like I warged into a college student’s body. And this part ain’t Lisa Loeb’s fault but my immediate response was, like, revulsion, like, Oh god, I don’t want to be in college, arrrrrrgh. I guess that’s preferable to any other reaction. Depending on your personal history, be careful with this Purple Tape, is what I’m saying.

That’s from the next song, called “Train Dreams,” and I will be honest and say that my first reaction was, like, well, this ain’t exactly Ani DiFranco in terms of scouring, literary, bare-knuckled hostility. But Lisa’s deliberately childlike vocabulary and imagery, it gets to you, it grows on you, it grows in you. She’s got a few great early songs that convey a sentiment she summarizes as, You’re really dumb but you used to be cool. Great song genre.

So we got a young, quiet, but quietly quite bold singer-songwriter gigging constantly in the quite vibrant early-’90s Manhattan acoustic-café-type scene, handing out copies of The Purple Tape and making industry connections and learning about the music business and going to seminars like CMJ and shit, and also she’s got an apartment down in the Village on Mercer Street near NYU, and in fact she lives across the street from young, famous actor Ethan Hawke, and they get to talking, and Ethan’s got this movie Reality Bites coming up, and it’s not that simple, but it’s kinda close to that simple. Apparently first Lisa was invited to take a shot at writing the song “I’m Nuthin’”—apparently they really wanted a song in this movie called “I’m Nuthin’”—and I’m guessing her version was better, but they didn’t use her version. So then later Ethan goes to see Lisa play a show, and he likes another song of hers, and he passes a tape of that song on to Ben Stiller, and boom, it’s playing over the end credits to Reality Bites and hits no. 1, and, yeah, relative to the usual convolutions of the music industry, it’s all pretty simple.

She wrote it, initially, for Daryl Hall. As in, Hall & Oates. Hall & Oates as in, like, “Sara Smile,” speaking of rad classic-rock songs from the mid-’70s. She heard Daryl Hall was looking for songs for a solo album. That makes sense. Daryl Hall singing “Stay (I Missed You)” makes sense. But this was destined to be Lisa Loeb’s song. Her breakout. Her historic, unprecedented, somewhat shockingly chart-topping breakout song. Recorded in a two-bedroom apartment on 52nd Street between 9th and 10th with her band, Nine Stories. It should be clunky but I always dug how that name flowed: Lisa Loeb and Nine Stories. It’s a J.D. Salinger reference. Her sound, as exemplified by The Purple Tape, doesn’t need a ton of embellishment. Just a tiny, tasteful amount of embellishment sounds just miraculous.

The harmony on the word naive, man. I can’t believe this song isn’t in the movie itself. Just the credits. There’s the whole montage, right near the end, where Ethan Hawke and Winona Ryder are torn apart and missing each other, and he’s smoking in a hospital right next to a giant No Smoking sign, and she’s smoking and moping over a beer at the cool rock club, and this is a set of circumstances that calls, quite explicitly, for a song called “Stay (I Missed You),” but no, the montage song is U2’s “All I Want Is You,” which, OK, that’s secretly a top 10 U2 song, but even that song is from 1988. It’s from another movie.

To hear the full episode click here, and be sure to follow on Spotify and check back every Wednesday for new episodes on the most important songs of the decade. This excerpt has been lightly edited for clarity and length.