This World Is Bullshit: Fiona Apple, the 1997 VMAs, and the Astrology of Radical Authenticity

Aug 1

A Case Study in Asteroids, Eclipses, and the Dynamics of Misunderstanding

This article was originally published in the NCGR-NYC Spring 2025 newsletter The Ingress. I have formatted the article to fit substack format. Special thanks to Howard Moore for his guidance and assistance on inspiring coaching and helping me write my first article

A few weeks ago, I attended the NCGR’s Special Interest Group on asteroids, hosted by astrologers Amy Angelo and Lori Kaufman. Early in the session, Amy shared asteroid Memoria (1247) was exactly on the Ascendant for the meeting, which also happened to be conjunct my natal Moon.

The group met between eclipses, in that potent liminal space where the past resurfaces and the future hasn’t quite landed. As the conversation deepened, I found myself thinking: Who or what from my own memory could I bring forward?

Fiona Apple showed up in my mind’s eye , specifically, her unforgettable speech at the 1997 MTV Video Music Awards. You know the one:

“This world is bullshit.”

Fiona’s Chart: The Asteroid Dimension

Fiona Apple’s natal chart is rich with asteroid conjunctions that illuminate the deeper mythos behind her artistry and her life. As Demetra George writes in Asteroid Goddesses:

“ When Asteroid themes are prominent in an individual’s chart, they denote a personality in which the power of the transformative principle can be operative. Often these persons become vehicles in the general society through which old, crystalized structures, attitudes and values are destroyed, then renewed and regenerated. Consequently, their lives are marked by crises of individuality challenging the established path of mass consciousness.” (pg.10) (1)

Let’s dive into the pileup of asteroid activity in her chart, especially around her Ascendant and key angles.

♏️ The Scorpio Rising + Ceres Pileup

Ascendant: 0° Scorpio
Ceres: 1° Scorpio
Part of Fortune: 2° Scorpio

This trio gives Fiona her intense magnetism and depth, but Ceres adds a nurturing edge — the mother archetype, yes, but also the one who descends, who searches, who returns from the underworld changed. At just 19, Fiona was mothering her own trauma through music. And listeners felt it. Tidal wasn’t just a debut album — it was a lifeline for anyone who needed permission to feel.

🌿 Descendant: Chiron + Minerva

Chiron: 5° Taurus
Minerva (93): 29° Aries

Across the way, we find Chiron on the Descendant — wounding and healing through relationship, misunderstanding, and mirroring. With Minerva, the Roman Athena archetype, close by, Fiona has the strategic wisdom of an outsider who refuses to play along.

🌓 Midheaven + Proserpina

MC: Late Leo
Proserpina (26): Conjunct MC

This asteroid — the Roman Persephone — sits on her Midheaven, the point of public life and visibility. The girl who was taken underground becomes the woman who reemerges with the power of both worlds. Her fame was never going to be simple.

💫 Lilith Crossroads

IC: 5° Aquarius
Lilith (1181): 0° Aquarius

This IC-Lilith conjunction squares her Scorpio Ascendant and opposes Proserpina. The symbolism? Shadow work. Refusing to betray the feminine. Family dynamics that reject compliance. Lilith demands authenticity, even at great personal cost.

🌕 Virgo Stellium: Sun, Moon, Vesta & More

Moon: 19° Virgo
Sun: 21° Virgo
Vesta, Diana (78), Demeter (1108): 19°–23° Virgo

The Virgo archetype here is about sacred service. Conjunct the Moon and Sun, Vesta channels devotion. Diana brings wildness. Demeter, again, echoes Ceres: this is a chart filled with divine feminine recovery. It’s no surprise Fiona idolized Maya Angelou, another woman who reclaimed her power through words.

💽 Tidal & The Eclipses That Framed It

Fiona Apple’s debut album Tidal dropped on July 23, 1996—but the stars were already staging a reckoning.

Just months earlier, on April 4, an eclipse landed on her Pluto, North Node, and Hygeia. This launch, coincided with her nodal return, events pointing to the path of souls’ journey, destiny

Chiron (the wounded healer) sat with Pallas (wisdom and justice),
who sat with her Ascendant in Scorpio.
A call to voice deep truths, even when they cut. Even when they’re inconvenient.

Then came the April 17 1996 solar eclipse at 28° Aries—just 2° from her Descendant.
The public would see her. And judge her.

Her 1996 Solar Return told the same story:

Cancer Rising (Moon-ruled, sensitive, intuitive)
Saturn on the South Node in the 10th, squaring the Ascendant = karmic tension around fame

8th house profection year: Uranus opposite Mars, Diana opposite Venus — rebellion and raw truth.

🕊️Caged Birds Maya Angelou, Synastry

Fiona always cited Maya Angelou as a core influence.

Their charts show karmic mentorship:

Chiron conjunct Chiron
Maya’s Moon on Fiona’s Pallas (wisdom from the feminine)
Maya’s Neptune on Fiona’s Saturn
Maya’s Sun-Jupiter on Fiona’s South Node

Both Chiron in Taurus faced early experiences with assault. Their journey’s on finding stable ground through their lives and self worth in the process expressed potently in their art.

🗓️ 1997 VMAs: A Speech Between Eclipses

The 1997 VMAs were held on September 4, smack between a solar eclipse on September 2 and a lunar eclipse on September 16. Eclipse season is never ordinary — and neither was Fiona’s speech.

Let’s look at the sky:

Mercury retrograde was on her natal Mercury (retrograde) — in her 10th house of career
The North Node was conjunct her natal Sun — destiny spotlight.
Lilith was conjunct her Vesta — sacred rebellion.
Chiron was still on her Ascendant and Ceres ‘ wounds made visible.

And that lunar eclipse on Sept. 16? It landed at 23° Pisces, directly opposite her Virgo stellium — her identity, her voice, her emotional truth.

And what did she say?

So, what I want to say is, everybody out there that’s watching, everybody that’s watching this world? This world is bullshit. And you shouldn’t model your life about what you think that we think is cool and what we’re wearing and what we’re saying and everything. Go with yourself. Go with yourself... And it’s just stupid that I’m in this world, but you’re all very cool to me so thank you very much.

💔 Misunderstood — and Ahead of Her Time

The backlash was swift and brutal. Fiona was called angry, ungrateful, and self-destructive. But she wasn’t angry — she was honest. In a 1998 Rolling Stone interview, she explained that the award made her feel like a sellout. People were praising the illusion, not the art. “I’d betrayed my own kind by becoming a paper doll,” she said.

When I won, I felt like a sellout...[and] the recognition I was getting was for the wrong reasons. I felt that now, in the blink of an eye, all of those people who didn’t give a fuck who I was, or what I thought, were now all at once just humoring, appeasing me, and not because of my talent, but instead because of the fact that somehow, with the help of my record company, and my makeup artist, my stylist and my press, I had successfully created the illusion that I was perfect and pretty and rich, and therefore living a higher quality of life. I’d saved myself from misfit status, but I’d betrayed my own kind by becoming a paper doll in order to be accepted.

This is the heartbreak of the asteroid archetypes: they speak a language most people aren’t ready to hear.

🌌 Go With Yourself

Fiona never strayed from her authenticity even when the odds were against her. Her Ceres-Lilith-Chiron-Proserpina grand cross vibrantly provides deeper clarity on how misunderstood she was. The fated quality of the eclipses and the tango of transits during the first few years of her fame show that she needed to be misunderstood in order to be appreciated and better understood years later. As the world changed, her message always stayed the same: “Go with yourself.”

She never changed. We did.

(1) Demetra George and Douglas Bloch, Asteroid Goddesses: The Mythology, Psychology, and Astrology of the Re-Emerging Feminine (San Diego: ACS Publications, 1986), 10.