‘Shadowboxer’: Fiona Apple’s tragic tale of teenage infatuation

Fiona Apple might release records at a rate that makes Guns N’ Roses look like Guided By Voices, but if anyone’s earned the right to, it’s her. Five albums over the course of nearly 30 years may seem like the work of an artist in need of inspiration, but, if anything, the opposite is true. For Apple, especially on her most recent records, the struggle seems to come from translating her radical, unstoppable creativity into records that a major label can sell.

That said, Apple might also be the sole artist for whom hoping that she releases some music that sounds like her early work isn’t an example of craven nostalgia. After all, Fetch The Bolt Cutters is a masterpiece, but no more of a masterpiece than Tidal. That album would be a once-in-a-generation achievement if it came from any singer-songwriter with miles on the clock, but the fact that it was the debut effort of a 19-year-old who wrote most of its songs when she was three years younger is a miracle.

‘Criminal’ may be the most recognised song off the album, and fair play to it, it’s one of the best songs of the 1990s. However, the key to the whole record might just be its lead single ‘Shadowboxer’, a cut whose strutting, low-slung sultriness hides a dark, wounded core. The kind that you can miss among the hooks that it keeps throwing at you, along with Apple’s staggering vocals, before you realise the darkness in the song has been staring you in the face the whole time.

That darkness would have been harder to miss at the time, though. Apple’s rise to mainstream stardom in the mid-1990s shows that not only was she a teenager, she was an authentic, undiluted one at that. Teenage pop stars are dime-a-dozen at the moment, but looking at them, one gets the feeling that each of them has been primed for stardom since grade school. Fiona Apple was not one of those kids, much to her detriment.

How was Fiona Apple a different kind of superstar?

Fittingly for a woman who accepted an MTV Award for ‘Best New Artist’ with the words “this world is bullshit”, Fiona Apple didn’t really have a filter when she arrived onto the world’s stage. Rather than the media-trained stage school kids who came after her, she answered any question that came her way with disarming honesty. It’s the reason we know, in pretty exacting detail, the complicated relationship that inspired ‘Shadowboxer’.

When asked by NUVO what inspired the song, Apple naturally didn’t hold back. She said it was a past lover, elaborating, “I really loved him. I felt that he was my best friend. But he was a teenage guy, and they don’t think a lot of times. He mistreated me, and then he came back. I couldn’t even be friends with him for a while… I knew that he just wanted to be friends with me so he could have the option of making a move on me whenever he wanted to.”

Being open about a situation like that would be more than enough for the promo trail. Typically, Apple opened up more: “Because I was so infatuated with him, and even in love with him, I was always available for that. It made me feel weak every time I would fall for that. And I would look forward to him making a move on me, but I knew that it was wrong. I knew that he was playing with me. And after a while, I didn’t even care anymore because I wanted him so much.”

Thus, she creates the artful metaphor of a shadowboxer, striking at darkness because “I wanna be ready for what you do”. The line between being ever-ready and quite literally being scared of the shadows growing thinner by the day. I cannot stress this enough, but this was the level of songwriting mastery that Fiona Apple began her career with, and she’s just gotten better since.

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