Mockumentary ‘The Last Head Shop’ Pays Homage to ‘90s New York City
For Merchant director Lenski, and many others who got to experience it, New York City in the ‘90s was something else. Packed with weird, chaotic subcultures and underground economies, the city, prior to its Rudy Giuliani-driven push toward something corporate and sanitised, was something you really had to experience for yourself – a worthy subject for a film, undoubtedly.
This is exactly what Lenski, alongside AI artist Sy Goldstein, wanted to pay homage to in their latest collaboration, a mockumentary titled ‘The Last Head Shop’. Serving as a way for the director to capture what he remembers of this era, the work depicts New York in all its grunge glory… but with a twist. Centring on the concept of ‘skull dealers’ – a fictitious concept which is exactly what the name implies – this abstraction serves as a satiric stand-in for those lost offbeat industries that once thrived before Times Square got its Disney makeover.
Of course, seeing as skull dealers and shops never existed, this posed some technical challenges. From using AI to generate imagery, to incorporating audio interviews, archival footage and original music to ensure each scene felt as though it was sourced over decades, this film was a massive undertaking from start to finish. So, to learn more about the process, as well as why this version of New York was something worth depicting, LBB’s Jordan Won Neufeldt sat down with Lenski for a chat.
LBB> Starting from the top, where did the idea for ‘The Last Head Shop’ come from? What made this a story you wanted to create?
Lenski> AI didn’t come up with this idea; if it had, it would’ve been about a skull shop with perfectly symmetrical skulls and inspirational neon signage. Instead, I wanted to capture a version of New York that felt true to my memories but wasn’t real at all – an alternate history wrapped in nostalgia. The idea of an underground skull trade was just the right mix of absurd and oddly believable – a way to satirise the city’s transformation in the ’90s while leaning into the myth-making that happens when a place changes beyond recognition.
LBB> Specifically, where did the idea of skull shops come from? Why was this the right way to capture a forgotten part of New York City, but in a fictional way?
Lenski> The idea of skull shops started with an AI-generated image by Sy Goldstein, but at its core, the film is about the erasure of New York’s weird, chaotic subcultures. Rudy Giuliani’s ‘clean up’ of the city in the ’90s crushed underground economies and replaced them with something corporate and sanitised. The skull trade is a stand-in for those lost spaces – absurd, but reflective of the real, offbeat industries that once thrived before Times Square got its Disney makeover.
LBB> What was the storyboarding process like? How did you combine your memories with an abstract concept to create something original?
Lenski> The key was to blend absurdity with authenticity, making it feel like a real, lost piece of New York history, even while the premise remained completely fictional. The first edits were almost entirely AI-generated stills – hundreds of them – acting as something between storyboards and an animatic. This let us shape the visual language before committing to the final sequences.
LBB> From here, what was the writing process like? How did you capture the documentary-style tone throughout?
Lenski> Rather than scripting traditionally, I recorded improvised interviews with an actor playing the skull dealer. This gave the dialogue an organic, lived-in quality. We then structured the best moments into a loose documentary framework, layering in archival footage to blur the lines between fiction and reality.
LBB> The narrator's voiceover feels spot on for the genre. Who did you cast for this, and how did you work with him to bring out a strong performance?
Lenski> We approached the voiceover like a real documentary, setting up a full backstory for Jonny Sollis to improvise from while I played the documentarian, interviewing him on the streets of New York. That process gave everything an authentic, lived-in feel.
Jonny, a real New Yorker, brought just the right mix of authority and world-weary nostalgia, and some of the best moments came straight from his unscripted tangents.
LBB> Of course, we have to discuss your use of AI! How did you ensure from the get-go that it'd elevate, and not replace the artistry?
Lenski> AI isn’t replacing filmmaking anytime soon – it takes forever, is wildly unpredictable, and feels like working with a picky creative director who won’t tell you what they want but knows exactly what they don’t want.
From the start, the goal was to use AI as a tool, not a crutch. Sy handled the AI-generated visuals, but everything else (narrative structure, performance, editing, music, sound, and finishing) was deeply human. We made sure every AI-generated element was shaped by real storytelling instincts, and wasn’t just dropped in as a gimmick.
LBB> Let’s talk more about the use of archival footage. What was the gathering process like, and how did you work to integrate it into the project?
Lenski> We dug through footage from the era when Times Square was being ‘cleaned up’, looking for moments that could be recontextualised or satirised. The goal was to weave real history into our fictional world, blurring the line between fact and fabrication. Our editor, Aaron Langley at Cosmo Street, really pushed this to the limit, finding the perfect clips to amplify the absurdity while keeping it grounded in the visual language of the time.
LBB> For each clip, you also sourced original audio and ran it through the telecine to make it feel authentic. What was this process like?
Lenski> Phil Loeb at Heard City handled the mix, giving the audio that archival, aged quality. Then, Tim Masick at Company 3 did the telecine work, treating each clip like it came from a different source – some grainy, some overexposed, some with weird tape glitches – to mimic the inconsistency of found footage.
LBB> What were some of the biggest challenges you encountered while filming, and how did you overcome them?
Lenski> The biggest challenge was making the AI-generated elements play right in a full story; organic, not stiff or uncanny. That’s why we leaned into VHS textures and analogue treatments, to break the digital sterility AI can sometimes create.
Also, balancing AI’s role without it overshadowing the storytelling was key. It had to be a film first, an experiment second.
LBB> What lessons have you learned throughout this entire process?
Lenski> That AI is like an intern with big ideas but zero follow-through – it can generate, but it can’t decide. The real work still comes down to human taste, storytelling instincts, and sheer perseverance.
I also learned that making something feel real takes way more effort than just making it look cool. Every choice from sound design to editing and VHS textures was about grounding the absurdity in something that felt like it could’ve been taped off a TV in 1993.
LBB> Finally, is there a part of this project you're most proud of?
Lenski> That we made something completely fabricated feel like a lost piece of New York history. Blurring the line between nostalgia and invention was the goal, and I love that people aren’t quite sure what’s real and what’s not. Also, that we wrangled AI into being useful instead of just... AI-ing. Honestly, getting it to behave felt like training a dog that only understands vibes.
