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Harry Waldman: his projects and the real story behind his award winning short Enter The Room.

Updated: Apr 15, 2023

Harry Waldman is a passionate filmmaker who has been watching movies since as long as he can remember. Some of his favorite films include "Memento", "The Dark Knight", The Lord of the Rings" trilogy, "Alien", etc. He has seen nearly 8,000 films and he says he is as crazy about movies as any individual you will ever meet. He studied Business at Ithaca College and ironically figured out his passion right as he was graduating. He has worked on a number of various films he has written, directed, and edited "515", "Enter the Room", "In the Backseat", "Bay For Blood" and "The Corridor Crossing". He has a few more projects in the pre-production stage.

Hi Harry, thank you for being here, can you please summarize Enter The Room to our readers?

H- A young adult (Brian) is visited by his brother, Jeremy, who needs a place to stay as he settles into his new city. The two polar opposite personalities begin to clash as Jeremy's presence poses a threat to Brian's way of life. Brian's uptight personality and unreasonable living standards rub off on Jeremy, creating an incredible amount of tension. Bad blood, stemming from a traumatic past event reveals the shocking truth of the brothers' current situations, as Brian struggles to differentiate between reality and his worst nightmares.

Peter Marten (Brian )and Rich Holton (Jeremy)

What inspired Enter The Room?

H- My relationship with my roommate during the first semester of my freshman year of college is what gave me the idea for “Enter the Room”. Almost all of the various things that Brian was getting on Jeremy’s case about during the narrative were actual things that my roommate accused me of. (And there were other things he said/did to me that I wasn’t able to fit into the film) Living with him was a very unpleasant experience for me, and I felt that I needed to get it off my chest by telling this story. In addition to Brian being based on my college roommate, I added a disturbing and tragic backstory about him and decided that he and Jeremy being brothers would make for a more interesting narrative. While I am not nearly as uptight as my college roommate was, I can be a bit neurotic, so I took “pieces of myself” which I injected into Brian in order to make him more layered. In general, I believe that creating complex characters often requires giving them flaws that can make them unlikeable at times, and I always do my best to try to walk in the shoes of the anti-hero or villain in order to portray them in a more genuine manner.

from left: Lance Eliot Adams , Harry Waldman and Mohamed Nazar

Which filmmakers inspire you? And why?

H-Christopher Nolan was the first film director who I specifically followed. I first watched one of his earlier films, “Memento” at a friend's house in 7th grade. It was actually his parents' recommendation, and I was a rebellious kid, so I was skeptical. I was quickly proven wrong, and while I was confused by the twist ending, I was also very intrigued and immediately wanted to watch it again. I forgot about the film for some time, and about 2 years later, I stumbled into it at a Blockbuster. I became so obsessed with the movie that I watched it 5 nights in a row, learning something new every time as Christopher Nolan dropped so many Easter eggs throughout the film. In general, I really prefer to watch new films and I often get tired of repetition, but "Memento" is one of the few films that I can revisit over and over without ever becoming even slightly bored with it. Due to the ingenious plot structuring, smart script, incredibly complex characters and insane twist ending, "Memento" is the first film that I became obsessed with and is still my favorite film to this day. When I saw “Batman Begins” in theaters a few years later, I was blown away by the darker, more serious tone that the film went with and saw Christopher’s name in the credits as the Director shortly after the film ended. That was the moment that I learned of the influence that a director can have on a film and have followed Nolan closely ever since. There are so many other directors who I follow, but I would say that some of the others who have definitely had an influence on my work include Danny Boyle, David Fincher, Gaspar Noe, Alfred Hitchcock, Stanley Kubrick, David Lynch, Akira Kurosawa, John Carpenter, Satoshi Kon, Michael Mann, Brian De Palma, Phil Lord and Christopher Miller. I have had a number of family, friends and acquaintances compare my filmmaking style to David Lynch after watching “Enter the Room” which I take as a gigantic compliment.

Harry Walkman on set with Steve Wester Gaffer and Lance Elliot Adams Producer and DP.

You previously said that you graduated in Business at Ithaca College, that's where you discovered your true passion. What made you change your path?

H- I found myself not paying attention during most of my Business classes as the content just didn't interest me. My Second Semester of my Junior year of College was when my eyes were opened as I took a Personal Essay class with a Professor who my friends warned me about, saying he was a tough grader. Not only did I receive a very positive grade in his class; I had so much fun writing stories about myself. After I took this course, I began to question if it was a problem that I could barely pay attention in most of my classes, whereas I looked forward to going to this class. About a year later, I finally realized that storytelling was my true passion.

Peter Mastne (Brian)

This short has an excellent cast how was your casting process?

H- Thank you for your kind words. My friend and the Producer of the film, Lance Eliot Adams, made posts about the film on Breakdown Express (Actors' Access for Actors) and Craigslist. After the talent posted for our project, we auditioned a handful of actors at a theater one night and Lance, the Assistant Director, Mo and I came up with the conclusion that Rich and Peter were the best fits for their respective roles in addition to being very talented actors. Since this film, I have produced my own films and led casting, expanding on everything that Lance taught me, posting to a handful of different casting websites. I try to bring at least one casting expert onboard to help me find not only the actors/actresses who have talent, range and seem connected to what they are saying, but also those who are the correct fit for their roles and seem professional enough to work with. One interesting note about our casting process during "Enter the Room" is that while I realize that it is normal to have talent read lines for the auditions, Lance decided to have them perform their own monologues. On my films since, I will have the initial audition involve monologues and the callbacks will involve the actors/actresses reading sides with each other.

Rich Holton (Jeremy)

The chemistry between your actors is incredible, tell us about your vision and your modus operandi. H- Thanks! I envisioned Brian as very neurotic and uptight, whereas Jeremy was supposed to be more laid back, but a bit messy and arguably inconsiderate at times. Peter and Rich naturally read a lot like their characters, which made the process pretty easy for me. I also do like to think that I have a pretty specific attention to detail and provide many notes, which allowed for them to properly get into character for the film shoot.

We noticed very symbolic cinematography, the short's look is impeccable. What was the process behind this behind it?

H- I appreciate the compliment! I used a lot of close-up shots on the characters to capture their wide range of emotions conveyed throughout the film. And the single shots (as opposed to two shots) were often used to give the audience a cold and distant feel in which the characters feel isolated from each other, which is the case for the brothers in reality. The low angle shots looking up for the big argument were key to make the characters look more intimidating. I do believe that my cinematography for my films since have become a bit stronger as they include more motion, longer takes and more variety of types of shots in general, but I do feel that the shot selection plan was executed successfully for "Enter the Room".

What was the biggest challenge for you?

H- As this was my first professional film, while there were a lot of obstacles that I faced, the toughest one had to be scheduling the shot list. While I think I had a decent knowledge of cinematography at the time, I didn’t fully grasp the importance of saving time by tactically picking and choosing the order of shots that would be captured throughout each day. This mistake led to more lighting and camera setups throughout the shoot than was necessary. Fortunately, my Assistant Director, Mo Nazar, was on point during the entire shoot and really helped to keep things moving quickly. Because of this, we were able to finish the film in about 2 2/3 shoot days even though we had initially scheduled 4 days for the shoot. In general, properly scheduling a shot list is something that I have struggled with and stressed over consistently, and if I am ever able to direct films with a larger budget, I will prioritize using some of that budget to hire someone who can specifically help out with this in order to keep the film shoots flowing efficiently and smoothly.

Harry, please, blow our minds, share with us a fun fact about your short.

H- Every single thing that Brian got on Jeremy's case about were real things that my college roommate called me out on. There were actually a lot of things he called me out on that couldn't be included in the film due to me not wanting to make the film too long.

Wow, did your former roommate ever find out? If so, what did he do about it?

H- I believe he is not currently aware of the film. To be honest, I don't know how he would react if he saw the film and knew it was based on our relationship.

This short has a psychological impact on the audience, what was your purpose psychologically wise?

H- My purpose was at first for the audience to loathe Brian and be very irritated by him, but as the film progressed to gain some empathy for him and understand the reality that anyone can be turned to the dark side after going through a tragic experience.

Did you work during Covid 19? How did that affect you?

H- I did work at my full time Post-Production job, but my hours were cut and the company struggled for a bit as they focus mostly on weddings and the wedding season died for a time. It had a pretty big effect on me psychologically, but what the toughest part for me was not being able to make my own films as I have been obsessed ever since I began making them. Fortunately, I have been much happier since COVID has calmed down and feel like myself again now that I can continue to make my films.

You come from Chicago, how's the film industry in your area, what would you change?

H- There are a decent amount of filmmakers out here and they are very supportive overall. I am happy with the industry out here, but I would love if there were more film festivals in Chicago, especially because it's such a large city.

Harry Waldman and his cast and crew on set. From left Mohamed Nazar AD, Lance Elliot Adams Producer and DP, Cody Adams Location Manager and Sound, Ryal Zeller Gaffer.

What's the best part of your job, what's your favorite step in the process?

H- It's editing, whether for my full time job or my own films. Editing is where the story really comes to life in my opinion, and it is so satisfying to see everything come together, especially if the film comes close to how you initially envisioned it. Writing is a close second and is arguably the most important part of the process in my opinion.

If you could choose between editing and directing, what would you choose?

H- As much as I love editing, I would choose directing, assuming that I would be directing my own personal story as I believe that I would have the most control over how the final product turns out. I also really enjoy directing, even if editing is my favorite part of the filmmaking process.

What would you say to someone that wants to start this path as you did?

H- First and foremost, I would not recommend becoming a filmmaker unless you absolutely love doing this and breathe it day in and day out as I (and a handful of filmmakers I have met) do. It is a long, expensive and stressful journey that often doesn’t come close to giving you back what you put in from a financial/recognition perspective. But if you truly love doing it and receive the level of satisfaction that I do from working on and completing your films, I think you should continue to push forward and hopefully things will work out. Even if they don’t, you will always have something to be proud of and no one can take away the satisfaction that you receive from completing your passion project. Second, understand how competitive this industry is, never expect anything and never act like you are owed something. Unless they had some incredible connection, even the best and most successful filmmakers on planet earth had to start at the bottom and grind it out in order to get to the top.

Be professional, kind and courteous to others, and always do what you say you are going to do. The film industry is very oversaturated and you need to do everything in your power to present yourself in the best light Third, just do it. I slowed my career down at times by stressing over trying something for the first time and not taking initiative, giving myself various excuses. Of course, you should plan ahead as much as you can, but studying is never the same as actually getting out there and doing it. Accept the inevitable fact that you will make mistakes, be flexible and move forward and you will learn from your mistakes and improve as you go. And last, just remember to enjoy the process and don’t focus too much on the endgame. I am currently editing my first feature film “The Corridor Crossing”, which I shot last spring/summer, and post-production is taking me a lot longer than I initially anticipated it would. I could obsess over this fact and make myself go insane, but I have instead decided to understand that this was my first feature film, so it is okay that I couldn’t properly estimate how long it would take to edit the film and simply enjoy the journey, which has been an absolute blast so far, despite all of the unexpected hurdles that I have faced to this point.

What do you regret and what would you have wanted to know earlier?

H- I regret not starting filmmaking earlier, which was due to my need to have a "normal and stable" job. I was too practical for my own good. And while studying and planning is important, I have learned that the best way to learn more about filmmaking (and in general) is to go out there and do it. You will make some mistakes, but will learn from those mistakes and grow from there.

What's your dream project?

H- My dream project is an animated film idea I have (I am obsessed with animated films and hope to consistently make them in the future) that involves a young adult (based on myself) who is going crazy because of being locked up in his apartment due to COVID. All of his personality types and emotions (Influenced by "Inside Out") work together through a handful of intense and intimidating trials in order to get his mood up and preventing him from doing anything drastic. (Throughout the film, he contemplates committing suicide, and they do everything in their power to prevent this from happening).

Who would you suggest this short to, and why?

H- My target audience is anyone who has ever had a roommate or family member who they clashed with. But even if you don't fall under this category, if you like dark, visceral and intense films that contain interesting characters and like stories that are rooted in realistic themes, you should enjoy this film.

What do you expect from the future? What do you hope it will bring you on a professional level?

H- I hope to slowly but steadily build my brand name and gain a decent sized following. On a professional level, I would love to receive funding from a Production company for future films, and it is my dream to get signed by A24. With that being said, I am happy enough simply telling my own stories and as long as I can save up enough money to continue to do so, I will be satisfied.

Your short won different awards with us, we truly enjoyed this work, how is it going with festivals so far?

H- It's going great so far! It's been selected into over 200 film festivals (More information about this is on my website and IMDB page) and has won a handful of awards. I didn't know what to expect when I started as is the first film I have submitted to festivals, so I am just so grateful that "Enter the Room" has had this much success.

Lastly, tell us about your past and future projects

H- I just shot my first feature film, "The Corridor Crossing" last spring/summer. The film is currently in the early stages of post-production. I have another short film, "Bay for Blood" that is in the later stages of post-production. I hope to have that one completed by next fall/winter and plan to submit it to festivals around then. And I am hoping to begin production for my next feature film idea, "Incautious" as soon as I finish my festival runs for "Enter the Room" and "Bay for Blood", which should hopefully be in the fall/winter of 2024. I would be happy to submit some of my future films to this festival once they are completed.

Thank you for your time, we wish you the best for your career and your future projects and we can't wait to see what's next for you!

H- Thank you! It was a blast chatting about "Enter the Room" and my filmmaking career.

Watch the traile of Enter the Room here:

Password: ETR18

Watch Enter the Room here:

Password: ETR18

If you want to contact Harry, email him at:



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