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In the Wee Small Hours: Eros and the Initiatory Descent
- Bradley Olson, PhD
- 7 minutes ago
- 8 min read
It was Sappho who first called Eros “bittersweet.”
No one who has been in love disputes her.
—Anne Carson, Eros the Bittersweet
When Anne Carson invokes the ancient lyric poet in Eros the Bittersweet, she is pointing to the fact that love is never simply one thing, one experience, one emotion. It is something both bitter and sweet. How we translate Sappho’s word, however, should give us pause. The original Greek word, glukupikron, is more properly translated as “sweetbitter,” but that just sounds wrong to the contemporary English ear. It makes more sense, though, doesn’t it? Love never begins by being bitter; it’s always sweet at the beginning, and only later does it become bitter—gradually at first, and then all of a sudden. More than sweetness, the bitterness is an unexpected, unsettling awareness of a boundary, while sweetness dissolves and defers the irksome experience of finitude. In either case, to encounter Eros is to discover that we are not entirely self-contained, and that the object of our desire is always already vexingly outside our control. The sweetness is inseparable from the bitterness of the beloved’s distance.
We tend to imagine mythological initiation as an ancient and rather dramatic affair: a youth led into a subterranean chamber by torchlight, or a medieval knight entering a dark forest at its thickest, most impenetrable point. But in modern life, our introduction to the sharp edges of love rarely occurs in such places. More often, it happens alone in the dark in the wee small hours around 3:00 AM, illuminated only by the glow of a cell phone’s Spotify playlist.
In 1955, Frank Sinatra released In the Wee Small Hours. If you’re not familiar with this landmark album in the history of music generally, and the Great American Songbook in particular, please take fifty minutes or so right now and give it a listen. Widely recognized as the first true concept album, Sinatra recorded it in the middle of his long, public, agonizing separation and divorce from Ava Gardner. In fact, Sinatra even called it “the Ava album.” His brilliant arranger, Nelson Riddle, remarked, “Ava Gardner taught Frank how to sing a torch song." It’s an extraordinary album: musically precise, lyrically intelligent, and so very...Sinatra. “The Voice” was never shy about publicly psychoanalyzing himself—he once called himself “an 18 karat manic depressive,” and with this album he documented his katabasis, his own descent into love’s underworld. Here, he serves as a kind of Virgil, guiding us through the distinct, painful levels of the sweetbitter, and I want to focus on a few of the tracks that best embody the album’s initiatory qualities.
“In The Wee Small Hours of the Morning”
“When your lonely heart has learned its lesson…”
The title track, the first song on the album, sets the stage. We’re informed that this is a voyage of learning, as all initiation is, of course. But what exactly is the lesson our heart learns? The song frames this early morning wakefulness not solely as a space for lament or self-pity, but as a classroom of the soul. I recall James Hillman saying that what awakens us at 3:00 AM are those considerations demanding, needing, our attention. Nelson Riddle’s arrangement for this song is understated: a lonely, muted horn to establish the ritual container. The initiate has crossed the threshold and is descending, trapped in the void after the collapse but before any mature understanding can take place.
It is not a matter of the ego “deciding” to go on a journey; it is the conscious mind being dragged down because its psychological attitude has reached an absolute limit. This is exactly how Sinatra sings "What Is This Thing Called Love?” This track captures the ego frantically trying to intellectualize its way out of the underworld.
“What Is This Thing Called Love?”
At this point in the descent, answers are needed because the question itself—What is this thing?—is an admission that the old ego-structure has no referent for this type of psychic experience. So the descent begins with confusion and interrogation. Interestingly enough, Cole Porter originally wrote "What Is This Thing Called Love?" in his typically urbane, insouciant pacing and style—the sort of song perfect for crowds and cocktails, for dancing amid peals of laughter in a night club or even a speakeasy. Sinatra and Riddle stripped all that away, slowing the tempo to something like a funereal dirge.
When Sinatra asks what is this?, he isn't posing a philosophical or existential question. He is standing in the wreckage of his marriage to the woman of his dreams, demanding answers from a force that has left him completely undone—and of course it was always bound to; Hesiod called Eros “limb breaker”—both destroyer and creator who gives humans to know both flights of ecstasy and the steep, nauseating descents of despair. Naturally, in the midst of this catastrophe, the sophisticated easy-come, easy-go persona has all but disappeared, leaving only the disturbing realization: the ego is no longer in control.
It is not a matter of the ego “deciding” to go on a journey; it is the conscious mind being dragged down because its psychological attitude has reached an absolute limit.
“Ill Wind”
You're only misleading
The sunshine I'm needing
Ain't that a shame
It's so hard to keep up
With troubles that creep up
From out of nowhere
When love's to blame
So, ill wind, blow away
Let me rest today
You're blowin' me no good
No good
From questioning, from demanding answers, we witness the singer enveloped by a type of learned helplessness, a paralysis of the spirit. The lyrics are plaintive, or perhaps an attempt to bargain with the overwhelming forces of fate. And Riddle’s arrangement for this song is brilliant: woodwinds and strings mimic windstorms as though they’re whistling through a lonely apartment at 3:00 AM. The track transcends personal grief to capture the human condition, reminding us listeners that some forces in the human psyche are too massive to fight—they can only be endured.
"This Love of Mine"
Sinatra co-wrote the lyrics to "This Love of Mine" in 1941 when he was the featured vocalist for the Tommy Dorsey Orchestra. When he re-recorded it for this album in 1955, the song landed differently because of how he managed his breath.
As a young singer, Sinatra had closely watched Dorsey’s trombone technique, noticing how he could play long, unbroken phrases seemingly without taking a breath. By parting the very corner of his lips slightly while maintaining his embouchure on the trombone’s mouthpiece, Dorsey could inhale without interrupting the musical flow. Sinatra realized that if he could replicate Dorsey’s seamless instrumental phrasing, he could use his voice the same way Dorsey used his trombone to carry the listener through an uninterrupted musical phrase or thought.
On the 1941 recording, he sings the song as a conventional, mid-tempo big band ballad. On In the Wee Small Hours, he slows the tempo down, using that Dorsey-inspired breath control to stretch the lyrics into long, continuous phrases, while Riddle’s strings soften to match the velvety quality of Sinatra’s vocals. By the end of the track the struggle against the early morning wakefulness has ended in something like acceptance, or maybe just the determination to endure.
By the end of the album, the wound has closed, forming something like a psychic scar—a permanent part of Sinatra's style. Life goes on; he doesn’t know who he will be, but he knows he will never be the same:
I cry my heart out, it's bound to break
Since nothing matters, let it break
I ask the sun and the moon, the stars that shine
What's to become of it, this love of mine?
What will become of it, of course, is transformation. But these psychic transformations are hard to accomplish—and harder to endure. The psychic scar is no less real for being immaterial. While Eros inevitably proved to be adept as a “limb breaker,” we should remember that Hesiod also identified Eros as a foundational pillar of the primordial void out of which all of creation eventually issues. Eros is no small thing, and it begins to dawn on us why Sappho depicted Eros as a paradox. Eros isn’t only about limb breaking. When we’re wounded by love, the self comes into clearer focus; the scar reminds us of our own finitude—not just existentially, but in terms of limits and edges, too.
A scar is a symbol of healing, not of failure. A scar—physical or psychic—is no longer an open wound, no longer a site of pain and fear. It is a monument to living, ontic evidence that you’re alive and still in the game.
That’s the point of the initiation. It’s your lonely heart learning its sweetbitter lessons in the wee small hours of the morning.
Thanks for reading.
MythBlast authored by:
Bradley Olson is a writer, depth psychologist in private practice, teacher, speaker, and Director of Publications for the Joseph Campbell Foundation. His work explores the status of myth after belief—what it means to take myth seriously in a world where its metaphysical claims no longer hold in any straightforward way.
He is the author of The Mythopoetic Impulse and a Skeleton Key Study Guide for Pathways to Bliss. His current writing pushes against the dominant tendency to treat myth as a repository of timeless meanings or archetypes, arguing instead that myth functions as a form that brings the mind into contact with its own limits—where coherence breaks down and the desire for explanation remains.
Before his work in psychology and mythology, Olson worked as a police officer in North Dakota and Arizona. There, he encountered the world less as a smooth narrative than as rupture—moments of consequence without clear origin, human situations that resist explanation or moral symmetry. That experience continues to inform his understanding of myth—not as a system that resolves the world into meaning, but as a form that emerges in proximity to what cannot be made coherent.
In both his clinical practice and his writing, Olson is interested in how people live with those limits—how meaning persists, not as resolution, but as a problem that cannot finally be solved.
This MythBlast was inspired by the Initiation stage of the hero's journey and The Hero's Journey: Joseph Campbell on his Life and Work.
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