{Note: The Madonna Timeline is an ongoing feature, where I put the iPod on shuffle and write a little anecdote on whatever was going on in my life when that Madonna song was released and/or came to prominence in my mind.}

When last we featured a Madonna Timeline entry the focus was on the titular track of ‘Bedtime Stories’ from 1994. Today we go back even further – to that magical summer of 1990 – a summer that may go down as one of my favorite summers thus far in my mid-life. The hollyhocks were higher than we’d ever seen them, the sun was brighter and warmer than it ever felt before, and the first tinges of love and possibility were in the atmosphere. Helmed by an epic trip to the then-Soviet Union – our very first trip away from home for such a distance and such a duration – somehow we held onto the tenderness of youth while boldly bounding toward the first attempts at adulthood. That Madonna and Stephen Sondheim should write the soundtrack to such a time is brilliantly fitting. 

Having just been entranced by the magic that was ‘Into the Woods’ and its themes of childhood, growing up, and letting go, while also cresting into the white-hot pinnacle of my burgeoning fandom of Madonna, the soundtrack to ‘Dick Tracy’ was one of those moments where material, Madonna, and my own personal journey intersected for a touching musical moment. This song brings me movingly back to that time, and while it tells the pensive and tentative tale of a romance that never quite happens, for me it was more about an impending loss of innocence, something I sensed was happening, and something that I took with equal parts anticipation, dread, and resignation. 

The adventures I sought in the forests of Minsk, the laughter with girls at midnight – always safely platonic, always more lasting and resonant because of that – the stolen minutes in sun-lit hotel rooms before boarding the bus again – a summer in Russia held a romantic allure before any of us even understand the slightest about romance. From the bulbous towers of St. Basil’s Cathedral to the wild-flower-festooned meadows surrounding castles in Pskov, we traversed the country, in a whirlwind tour of cultural exchanges and adolescent drama. We learned and experienced as much about this country half-way around the world as we did about ourselves and each other. Our gang of friends solidified – a little group from New York meshing with a little group from California – bringing two sides of our country together while bridging our two countries, and in the exuberant innocence and wonder of that, we somehow made the world a little better simply by expanding our own limited views and experiences. Travel, and at such a young age, brought an early sense of humility and wisdom that has enriched and informed my ever-expanding journey ever since. 

What can you lose?
Only the blues
Why keep concealing everything you’re feeling?
Say it to her, what can you lose?
Maybe it shows
She’s had clues, which she chose to ignore
Maybe though she knows
And just wants to go on as before
As a friend, nothing more
So she closes the door

This duet between Mandy Patinkin and Madonna was a poignant cornerstone of the ‘I’m Breathless’ soundtrack and the ‘Dick Tracy’ movie – lending a grounded and human element to the over-the-top and cartoonish technicolor grandeur of that time period. So much of what Madonna did at that moment was glamorous and haughty, and as much as I loved that side of her, as much as I needed that side of her to push me to simply walk into a room of my peers when my social anxiety was pulling me back, I also wanted to see her vulnerability, to feel her own pain and loss and doubt. It selfishly made me feel a little better about mine. 

As our American troop returned from Russia to our homeland, I remember riding the bus back into Amsterdam, into our tiny hometown surrounded by fields of corn, and feeling different, like we had crossed the threshold into young adulthood, and understanding that we would not be going back. The evening sun was setting – the same sun that had illuminated Russian skies deep into the night – and the darkness was already coming on earlier than it had from when we had departed just a few weeks before. Can a boy grow into a young man on a single trip around the world? In some ways – in so many ways – I think he can. 

Well, if she does
Those are the dues
Once the words are spoken
Something may be broken
Still, you love her
What can you lose?

But what if she goes?
At least now, you have part of her
What if she had to choose?

As the Madonna Timeline is entering the winter of its run, and as we close in on the final songs still left unexamined in my collection, it seems a ripe moment to look over the other songs from the ‘I’m Breathless’ section of Madonna’s career. A unique album in a career of unique albums, this would be the closest Madonna would come to producing her own Broadway musical (‘Evita’ had already been written by someone else). 

• He’s a Man 
• Sooner or Later
• Hanky Panky
• I’m Going Bananas
• Cry Baby
• More
• Now I’m Following You Part 1
• Vogue

The album encapsulated the summer of 1990 – and as our People-to-People exchange group re-convened at my home a week after our return, already we felt the change and the oncoming chill in the air. I mourned the early summer sense of possibility that now felt behind us, growing ever-distant in the rear-view mirror, and the magical time in Russia with friends old and new, now once again separate and removed from the mundane moments that were once so special. Maybe I just missed my friends, and the day-to-day connections we shared only when in such close proximity. Maybe I missed the freedom of being more or less on our own at a time in our lives when we needed that first dose of independence. Maybe I missed my childhood, and the way it felt like Sondheim’s ‘No More’… 

It was one of those ‘Stand By Me’ summers, the kind that pass before we truly realize their magnitude and meaning. By the time fall crept into the nights, and the hollyhocks shriveled and browned, dropping some of next year’s crop of seeds onto the garden floor, holding up others high in the sky, I stood alone in the backyard, back where the summer began, and everything felt changed. Would I ever realize the magnificence of the moment during the actual moment? And did it even matter? Perhaps it was better to not understand the import of what was happening as it happened. Perhaps that would cripple us, stop us in our tracks. 

Leave it alone
Hold it all in
Better a bone
Don’t even begin
With so much to win
There’s too much to lose

Madonna put a fitting exclamation point on that summer with her performance of ‘Vogue’ in Marie Antoinette garb – all glamour and arrogance and nary a bit of vulnerability. Girding my loins for the school season to come, I channeled that and let go of the subtle loss of ‘What Can You Lose?’ It was an act of survival when the safety of summer slipped away, and somewhere in the secret recesses of my heart, I pulled the sacredness of those days tightly within that inner fortress. It has remained there, and I’ve only shared a bit of it with you because it’s still that important to me. Most of us retain some of our childhood in such secret fashion, keeping the most magical moments only for ourselves, and the ones who originally shared it with us. I’m not ready to lose that. 

Song #165 – ‘What Can You Lose?’ ~ Summer 1990