Q&A with Filmmaker Aaron Cassara, Director of The Hardest Working Man

Sep 18

Written By mark wantoe

The Hardest Working Man • Brooklyn Premiere • BFF 2026

Aaron Cassara’s documentary The Hardest Working Man follows Lorenzo Powell, a New York City shoe repairman carrying forward his father’s craft while helping New Yorkers preserve their cherished footwear. A Brooklyn Premiere, the film considers a vital artisan whose work has made him a fixture of midtown Manhattan for nearly two decades.

Cassara, a director, producer, cinematographer, and editor, brings a long-standing interest in documentary and narrative filmmaking to Lorenzo’s story. In the conversation below, he reflects on the family insight that became the film’s emotional center, the commitment required to see it through, and the makers who continue to define New York City.

Tell us about the moment this film began for you.

Wow! The film began in 2011 after Duane asked me to work on it. The first thing we shot were some time lapses of people walking through the city and then an interview with Lorenzo, which made it in the film.

What scene, character, image, or idea was the key that unlocked the film for you?

Alesia, Lorenzo's sister, is talking about her being upset with her father because Lorenzo couldn't go to college. Her friend then explains the value that Lorenzo received from his father and how it changed her perception. That quote from her is the crux of the film and why it's important.

The Hardest Working Man Trailer

Why did this story feel important for you to tell now?

I thought it was a great New York story when we started. Now that working people are under fire, it feels like it's getting out at the perfect time.

What was the biggest creative challenge or risk you took in making the film?

I don't think there were a ton of creative risks, but choosing to only focus on what happens in the shop and Lorenzo's family was a choice that started to unlock the structure of the film.

Was there a point when you weren’t sure you would finish the film? What kept you going?

It didn't feel like it was gonna get finished until we picture locked in 2024. I have to finish things that I start, so I just never gave up.

What surprised you most about the film as it evolved from the original idea to the finished work?

I'm used to films changing a lot, so I wasn't too surprised. I also don't start off thinking that it's gonna turn out a certain way. Especially with docs.

What do you hope audiences take away from experiencing the film?

I hope they get a warm feeling and are reminded of all the incredible makers in New York City.

Is there anything about this film, its inspiration, production, or your own journey that you think audiences should know?

I think for me it's just about how staying committed to the project got it done. I think some of the struggles that Lorenzo was going through when we were shooting have lightened because Broadway almost exclusively comes to him for all the shows' needs.

Based on your experience, what advice would you give to filmmakers just starting out?

If you want to do it, you have to fully commit.

What film, TV show, or other piece of storytelling did you see this year that you absolutely loved?

I screened with The Baddest Speech Writer of All at AMDocs. I thought that was one of the best films I've seen on the circuit this year.

If you’ve been to Bushwick the neighborhood, what do you love most about it?

I love the food and the art and warehouses.

What does “Make Time for Your Dreams” mean to you at this point in your creative life?

I think I've lived by that idea for a long time. It's just the way I live.

See The Hardest Working Man at BFF 2026

NEW YORK PREMIERE

Sunday • October 11, 2026 • 12:00 PM

Making A Life

Williamsburg Cinemas

Lorenzo, a shoe repairman in New York City, continues his father’s craft, helping New Yorkers maintain their cherished footwear.

GET TICKETS → https://www.bushwickfilmfestival.com/tickets

The 19th Annual Bushwick Film Festival returns October 7–11, 2026, bringing filmmakers and audiences together for five days of independent film, conversation, and community across Brooklyn

Aaron graduated with honors from Columbia College. He has spent the last fifteen years working as a freelance professional across television, film, and video. He has worked extensively as a DP, editor and producer.

🎟️

SEE IT AT BFF 2026

See The Hardest Working Man

NEW YORK PREMIERE

Sunday, October 11
12:00 PM
Making A Life
Williamsburg Cinemas

GET TICKETS

mark wantoe

Q&A with Filmmaker Aaron Cassara, Director of The Hardest Working Man

Tell us about the moment this film began for you.

Wow! The film began in 2011 after Duane asked me to work on it. The first thing we shot were some time lapses of people walking through the city and then an interview with Lorenzo, which made it in the film.

What scene, character, image, or idea was the key that unlocked the film for you?

Alesia, Lorenzo's sister, is talking about her being upset with her father because Lorenzo couldn't go to college. Her friend then explains the value that Lorenzo received from his father and how it changed her perception. That quote from her is the crux of the film and why it's important.

Why did this story feel important for you to tell now?

I thought it was a great New York story when we started. Now that working people are under fire, it feels like it's getting out at the perfect time.

What was the biggest creative challenge or risk you took in making the film?

I don't think there were a ton of creative risks, but choosing to only focus on what happens in the shop and Lorenzo's family was a choice that started to unlock the structure of the film.

Was there a point when you weren’t sure you would finish the film? What kept you going?

It didn't feel like it was gonna get finished until we picture locked in 2024. I have to finish things that I start, so I just never gave up.

What surprised you most about the film as it evolved from the original idea to the finished work?

I'm used to films changing a lot, so I wasn't too surprised. I also don't start off thinking that it's gonna turn out a certain way. Especially with docs.

What do you hope audiences take away from experiencing the film?

I hope they get a warm feeling and are reminded of all the incredible makers in New York City.

Is there anything about this film, its inspiration, production, or your own journey that you think audiences should know?

I think for me it's just about how staying committed to the project got it done. I think some of the struggles that Lorenzo was going through when we were shooting have lightened because Broadway almost exclusively comes to him for all the shows' needs.

Based on your experience, what advice would you give to filmmakers just starting out?

If you want to do it, you have to fully commit.

What film, TV show, or other piece of storytelling did you see this year that you absolutely loved?

I screened with The Baddest Speech Writer of All at AMDocs. I thought that was one of the best films I've seen on the circuit this year.

If you’ve been to Bushwick the neighborhood, what do you love most about it?

I love the food and the art and warehouses.

What does “Make Time for Your Dreams” mean to you at this point in your creative life?

I think I've lived by that idea for a long time. It's just the way I live.

See The Hardest Working Man at BFF 2026

NEW YORK PREMIERE

Sunday • October 11, 2026 • 12:00 PM

Making A Life

Williamsburg Cinemas

Lorenzo, a shoe repairman in New York City, continues his father’s craft, helping New Yorkers maintain their cherished footwear.

GET TICKETS → https://www.bushwickfilmfestival.com/tickets

The 19th Annual Bushwick Film Festival returns October 7–11, 2026, bringing filmmakers and audiences together for five days of independent film, conversation, and community across Brooklyn

See The Hardest Working Man

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