Interviews

Interview: “After Woodstock”: Howard Reiss Revisits A Generation’s Defining Moment Through Fictional Friendship

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Black and white image of author of After Woodstock, Howard Reiss

In After Woodstock, author Howard Reiss delves deep into the aftermath of a cultural watershed, blending memory and imagination to explore the evolution of friendship over five tumultuous decades. Set against the backdrop of the iconic 1969 Woodstock festival, the novel follows Jack and Bryan – two childhood friends whose lives diverge drastically after their shared coming-of-age experience in the mud and music of upstate New York.

For Reiss, who graduated high school just weeks before the historic event, Woodstock was more than just a concert, it was a transformative encounter with the ideals, contradictions, and possibilities of a generation.

“I graduated high school in June of 1969. I was naïve and, like a lot of teenagers, focused on myself and my place in the world,” Reiss recalls. “I played soccer, ran track and was at the top of my class. I was going to an ivy league school in the fall, and against the war in Vietnam, but didn’t do much more than debate about it. I was excited about the moon walk and attended Woodstock with a friend as a goodbye to our high school days.”

That spontaneous trip – just an hour and a half away by car – left an indelible mark. “The three days at the concert was an eye-opener in so many ways: drugs, women, politics, music, and life,” Reiss continues. “I had never been with so many friendly and supportive people, all about my age, all interested in having fun, experiencing new things and changing the world. It felt as if our generation had gathered not just for the music but because we had something to say and show to the world… I think that’s when I decided that my true religion would always be kindness.”

It was during those days, surrounded by idealism and youthful energy, that the seeds of After Woodstock were planted. “I went to Woodstock with one of my best friends and I always wondered what would have happened if one of us had decided to stay and live in a commune up there, while the other went out into the world to become a financial success as we always talked about doing,” Reiss explains. “Hence, Jack remains at Woodstock and Bryan becomes a successful lawyer. In truth, I think that Jack and Bryan are both me in my imagination; half of me stayed and became more Buddhist-like and the other half followed a more typical path.”

As the novel unfolds through a series of letters exchanged over fifty years, Reiss invites readers to consider not just the road taken, but the one left behind – and how the people we were at 18 continue to live within us. “The letters throughout the next fifty years are between my two selves, as much as they are between two childhood friends.”

A story told through correspondence 

The book cover of author Howard Reiss' novel After Woodstock

Buy the book now via Amazon.com

Reiss’s decision to tell Jack and Bryan’s story through letters is more than a stylistic choice – it’s a deeply personal one that aligns with the novel’s introspective tone and emotional depth.

“I like letters. I’ve always been a letter writer. And I’ve always loved receiving letters,” Reiss says. “There’s something special about hearing the voice of someone you care about inside your head, as opposed to standing there in front of you having a conversation. You think a lot more when you write a letter.”

For Reiss, the letter format allows the story to unfold with intimacy and reflection, while also tracing the arc of decades in just a few lines. “When you write a letter you have to fill the role of the reader as well to make sure they will understand what you’re trying to say,” he explains. “Letters can cover years and decades and show great changes in a paragraph or two. I wanted the readers to look forward to reading and writing the letters as much as Bryan and Jack did.”

Through this epistolary structure, After Woodstock offers a unique lens into how relationships, values, and identities evolve over time. It also reinforces the novel’s central theme – that meaningful connections can endure, even as life pulls us in vastly different directions.

Yet beneath the personal stories of Jack and Bryan lies a broader historical current. The late 1960s was a time of seismic social change, and Reiss doesn’t shy away from weaving these events into the fabric of his narrative.

The influence of these events on his characters is essential to understanding their worldviews. “I think Woodstock opened their eyes to the significance of what was happening at home, around the world and in space, in terms of politics, music, religion and science,” he says. “Their generation, our generation, had an important role in shaping the future to avoid war, encourage tolerance, end hunger, fight disease, take care of the earth, and show the world what we can always do if we work together.”

He acknowledges the idealism that surged during that era, recognising that such aspirations are not unique to his generation, but that few cohorts have experienced them on such a scale. “High ideals that I’m sure every generation has had at one time or another,” Reiss says, “although they don’t often get to share them with one half million of their friends and neighbours at a three-day concert.”

Still, Reiss remains conscious of how far the world has drifted from that spirit of unity and hope. “Unfortunately, looking around today, it does feel sometimes as if that Woodstock feeling is on life support,” he says. “Hopefully, another generation will pick up the torch.”

Love, friendship, and the long arc of change

While After Woodstock is deeply rooted in a pivotal moment in American cultural history, Reiss makes it clear that the story is as much about the lives that followed as it is about the festival itself. The decisions his characters make in the wake of Woodstock reflect the lasting emotional and philosophical impact of that weekend in 1969, especially for Jack, whose path veers sharply from the one he once envisioned.

“Finding love can change anyone’s trajectory,” Reiss reflects. “Jack was a math nerd growing up, he was uncomfortable in his own skin, but he had a creative and a philosophical side that kept him up late at night. Getting stoned with the girl he met at Woodstock, who had a very different view of life and love, made his choice to follow that inner artistic voice easier.”

That single relationship, forged in the haze of music and possibility, becomes a catalyst for Jack’s dramatic shift, a choice not just to change his plans, but to embrace a different way of being entirely. It’s a reminder of how formative moments, especially those experienced at a young age, can echo through an entire lifetime.

At the heart of After Woodstock, though, is not just individual transformation, but the enduring power of friendship. Jack and Bryan remain tethered by a bond that survives their diverging lives, offering a reflection of something many readers will recognise, whether from their own experiences or from long-lost connections that still live in memory.

“I have been blessed with a friendship that has remained strong for over six decades,” Reiss says. “It has required constant presence, but not in the physical sense. Jack and Bryan remain a constant presence in each other’s lives without actually being in each other’s lives. A friendship like that offers sustenance and helps sustain us through all kinds of ups and downs, much like love.”

Reiss’s portrayal of friendship isn’t sentimental, it’s grounded in emotional truth, the kind that withstands time, distance, and difference. And in a world that can feel increasingly fragmented, it’s a quietly radical act to believe in the kind of connection that doesn’t fade.

Looking back across more than 50 years, Reiss still sees the Woodstock ethos as not only relevant, but essential. “The ideals are still true – kindness, love, friendship, following your heart, treating everyone with respect, saving the earth, exploring your artistic soul,” he says. “They will never disappear and [are] always important goals. They get passed down from generation to generation. Hopefully, one of them will get it right.”

In choosing to tell this story as fiction rather than memoir, Reiss has also opened space to explore deeper emotional and philosophical questions, ones that are less about what happened, and more about what could have been.

“The what-ifs are always popular at my age,” he says. “After Woodstock is more about two friends’ lives after the concert than it is about Woodstock itself. Writing, as with all my other novels, opens a window for me on the lives of my others, as well as offering a mirror on my own.”

Ultimately, Reiss hopes his novel speaks not just to those who lived through the Woodstock era, but to younger generations as well, those who may only know the festival as a mythic moment from the past, but who still wrestle with the same questions about purpose, connection, and change.

“That life is all about change,” he says. “You can’t be afraid of it, and it’s never too late to follow your dreams.”

After Woodstock is out now in paperback (US), paperback (UK), Kindle, and audiobook

Dan Stephens
Dan Stephens is the founder and editor of Top 10 Films. He's usually pondering his next list, often inspired by his adoration for 1980s Hollywood, a time-travelling DeLorean and an adventurous archaeologist going by the name Indiana.

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