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‘60 Songs That Explain the ’90s’: Fiona Apple’s “Criminal” and Her Songs of Survival

Exploring the alt-rock icon’s early career with help from Ringer staff writer Katie Baker

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? On our show 60 Songs That Explain the ’90s, Ringer music writer and ’90s survivor Rob Harvilla embarks on a quest to answer those questions, one track at a time. Follow and listen for free exclusively on Spotify. Below is an excerpt from Episode 54, about Fiona Apple and her breakout debut single, “Criminal,” with help from Ringer staff writer Katie Baker. A warning: This episode features talk about sexual assault and eating disorders.

Fiona Apple McAfee-Maggart was born in New York City in 1977. Her father, an actor, and her mother, a singer, met while performing in the Broadway musical Applause, and split up when Fiona was 4. When Fiona was 7 or 8, she performed at a piano recital, playing a composition she’d written herself called “The Velvet Waltz,” which she’d much later describe to Rolling Stone by saying, “Oh, my God. It sounds like some kind of gay porn.” Fiona struggled in school, with bullies and such, though Shameika said she had potential. Fiona idolized Maya Angelou. She wrote poems. She kept journals. She wrote songs. She made a three-song demo tape, which she gave to a friend, which the friend gave to a music publicist for whom the friend was babysitting, and the publicist gave it to a guy named Andy Slater, who became Fiona’s manager and producer, and also managed and coproduced the Wallflowers.

Can I tell you about the guy this Fiona Apple song is about? Fiona’s ex-boyfriend who inspired the song “Sleep to Dream,” and many of the saltier songs on Tidal? Saltier as in salting the earth? Inspired feels like the wrong word. The guy who provoked this song? The guy who contracted this song, as one contracts a fatal, penis-shriveling virus?

His name’s Tyson. Tyson and Fiona met while he was rollerblading on the campus of Columbia University. They dated on and off for two and a half years. He moonlights as an acid-jazz DJ, or at least he did when Rolling Stone interviewed him for a 1998 Fiona Apple cover story about how she wrote a bunch of super angry breakup songs about him. He said, “I remember it being all my fault. Well, 95 percent my fault. I started seeing this other girl and liking her a little bit. And Fiona said one day, ‘I never want to see you again.’ And then a year later an album’s out.” Hahahaha. Tough break, Tyson!

So Tyson proceeds to tell this story about going away to college, and one day he’s making out with a young lady—some other young lady—and MTV is on, and the “Sleep to Dream” video comes on, in which Fiona Apple is seething in a replica of her old bedroom, and, as Tyson describes it, “Kneeling on the ground, looking through the TV, looking straight at me” as she sings words that remind Tyson of what she said to him the last time they’d spoken.

Tyson had to stop making out with that young lady. Tough break, Tyson. At the time, even if you weren’t privy to any of the proper names or any backstory whatsoever, when you heard “Sleep to Dream” on the radio or MTV, it was enough to know that you didn’t want to be whoever had inspired Fiona Apple to sing, “I have never been so insulted in all my life.”

I have to say, I’ve spent like 25 years so beguiled by “I have never been so insulted in all my life” that I never fully registered, “I could swallow the sea to wash down all this pride.” That’s a great line, also. And this, unfortunately, is a core component of the Fiona Apple multimedia experience: fixating on the most obvious thing to the exclusion of all even slightly-less-obvious things. Reading a Fiona Apple magazine profile or newspaper interview was just about the most dangerous thing you could do in the late ’90s. Rollerblading on the Brooklyn-Queens Expressway was less dangerous. Ideally, when reading these interviews you’d be wearing a helmet, or a hazmat suit. The New York Times interviewed Fiona in January 1997, about half a year after Tidal came out. The headline is, “A Message Far Less Pretty Than the Face.” The first two paragraphs read as follows:

“The pouty, bee-stung lips. The taut, pierced belly exposed by a flouncy shirt. The cascading honey-brown hair. And those eyes. Is this the next waif supermodel?”

“No. [This is the second paragraph.] Turn up the volume on MTV loud enough to hear Fiona Apple sing. She may look like a cross between Christy Turlington and Kate Moss, but Ms. Apple, a 19-year-old singer and pianist, has a voice—and a message—that make her looks irrelevant.”

I don’t want to belabor this. Tone-policing 25-year-old rock-star profiles is obnoxious and of limited utility. But I need to give you some sense of how bullshit this world is, precisely. People writing about Fiona Apple in 1997, collectively this was just an active, broiling, Pompeii-decimating volcano of YIKES. The discourse turns from crudely frivolous to bone-chillingly serious on a dime. For example: The far-less-pretty-than-the-face message, mentioned in that New York Times headline, is a reference to the second song on the Tidal album, which is called “Sullen Girl.”

Early on, at least one interviewer asked Fiona if this song, too, was about a bad breakup. It is not. Fiona Apple discussed, in multiple—in countless—magazine and newspaper profiles, the fact that she was raped, as a 12-year-old, in her New York City apartment building. Often she discussed this at excruciating length. Her description, in that Rolling Stone cover story, spans six, seven, eight paragraphs, of vivid and unsettling detail, down to the number of locks on her apartment door. She’d unlocked two of three. What she told Rolling Stone was, “I thought that ultimately, no matter what happens, if I lie about this, I don’t like what that says.”

And so now, in every interview, Fiona sat and waited for it to come up. Or she didn’t wait. She said, “I’d be, ‘You want to ask about when I was raped?’ I was, ‘Please don’t act like I have got food in my teeth. It’s out in the open. It’s not something that I’m embarrassed about, so don’t act like it’s something that I should be embarrassed about.’ Which I think I was sensitive about, because I was embarrassed about it for a long time.”

What’s often singularly great, but occasionally truly awful about listening to Fiona Apple sing is the way a random word can detonate the way the word my detonates there. The conclusion many early Fiona profiles arrive at—because Fiona says this explicitly—is that she writes her songs less as therapy than as a matter of outright survival. She describes songwriting, in that New York Times article, by saying, ‘’I didn’t think of it as a fun thing to do. I thought it was the only thing I could do.’’

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.