Screenwriter Spotlight: Winner Questionnaire (Dylan Wolf & Geoffrey Scheer.)
Having troubles finding something to write about? Not satisfied with the content of your screenplay? Feel like you are out of screenplay ideas?

By Chicago Screenplay Awards Dept.
Dylan Wolf
What’s your name and where are you from?
- My name is Dylan Wolf. I am from Saddle Brook, NJ
What’s the title of your screenplay?
- My screenplay is titled “Made Man Cleaning”
What’s the logline and how did you come up with the concept for your screenplay?
- The logline for my screenplay is: “Desperate for money, a man takes a job as a “private janitor” and is quickly thrown into a world of organized crime, revenge, and dead bodies galore.” I came up with the concept after a day of watching crime/thriller/mob films. You see all of these murders and messes of bodies, and it got me thinking who cleans it all up? What if they had their own in-house janitors? And it evolved into a “fish out of water” type story about an unsuspecting guy just trying to make some money, and he takes this cleaning job and now he’s helping cover up murders for the mob.
Tell us about your history as a screenwriter. Where did your journey begin?
- My screenwriting journey began about 6 years ago. I had made the shift from playing music to pursuing film. I feel that I’ve always done well in the writing department, and I have so many stories in my mind that I want to tell. I decided to pursue a career as a writer/director. Once I decided to start, there were many YouTube rabbit holes and educational book purchases. Eventually, I found myself seeking out more of an education. I found a local film school near me, NJ Film School, and took many screenwriting courses which helped me develop my craft immensely. All the while I just kept writing and writing. Both short films and features that lean to the horror/thriller/comedy lane.
What motivates you to be a screenwriter or filmmaker?
- The thought of being able to make a career out of telling visual stories excites me. I was never cut out for a 9-5 corporate desk job kind of life. I get bored too easily and seek out a change. Filmmaking excites me and having to adapt to any changing situation makes every day interesting. I thrive in a creative environment and there’s a satisfaction that being a filmmaker gives me. It really is true that my worst day on set is still better than any other job I’ve had.
What is the biggest challenge you have encountered as a screenwriter and filmmaker?
- The biggest challenge I’ve faced as both a screenwriter and filmmaker has probably been 2020 as a whole haha. As with a vast majority of people in the industry, dealing with a pandemic has definitely made things difficult in a variety of ways. Back in January/February, my producing partner and I were gearing up to film a few short films and then the lockdowns and rise in COVID cases put all of that to a halt. Toward the beginning of the pandemic, I was motivated and said to myself how I would get so many scripts done and use this time wisely. The reality of it was that it was difficult to be creative when there was so much uncertainty and anxiety of everything going on in the world. It was a rollercoaster of a year and there is some shaft of light coming from the other end of the tunnel, so I’ve been pushing myself harder than ever to create.
What’s the most important thing you want audiences to take away when watching your films or reading your screenplays.
- The most important thing I want people to take away from my films/screenplays is a feeling of being entertained. For me, watching a movie takes me to this special place. When going to the theater, I would feel like for the next 2 hours I am traveling into a new world with nothing else to think about. I want my films to help people escape the crappy stuff they may have going on in their lives, because that it is in turn what movies do for me.
Ideally, where do you see yourself in 5 years?
- In 5 years, I see myself having directed or sold at least one feature film and have continued plans to keep on creating bigger and better films.
What’s your favorite film of all time? If you can’t single out a film, give us your top 3.
- This is always the million-dollar question. I’ll go with the top 3 route (only slightly easier).
#1: Pulp Fiction/Inglorious Basterds (Tie)
#2: La La Land
#3: Drive
Honorable mentions to The Nice Guys and Hereditary.
What’s your earliest favorite childhood movie?
- My earliest favorite childhood movie would probably have to be either Raiders of the Lost Ark or Lord of the Rings. I’ve always loved action/adventure films growing up. Indiana Jones films were always so exciting (and terrifying seeing people’s faces melt at a young age) With Lord of the Rings, I want to say that that was the first movie I can think of that made me REALLY fall in love with cinema.
Who’s your favorite cinema hero?
- My favorite cinema hero, as much as its probably many people’s answer, Quentin Tarantino. His passion for films and film history is present in every frame of his films. He perfectly blends humor and suspense. His love for genre films is something I relate to very much. There are a few writer/directors that I look up to. More honorable mentions to Ari Aster and Shane Black.
Who’s your personal hero?
- Two people are personal heroes to me, still film related coincidentally. Adam Green and Joe Lynch. Both are established horror directors, and they have a podcast called “The Movie Crypt.” The community they have created with the podcast is such a great one and they enjoy interacting with the listeners and have given me advice on several things. Each week they interview people working in the film industry (actors, directors, cinematographers, writers, etc.) and it’s always a very open and honest conversation. Every episode ends with the question “what was your lowest point and how did you not give up?” The stories that people have told were both surprising and motivating. Every episode pushes me to keep going and not give up.
Geoffrey Scheer
What’s your name and where are you from?
Geoffrey Scheer. I was actually born in Chicago and lived in Des Plaines until I was eight. Grew up mostly around Washington, DC, went to college in Boston, lived in New York for eighteen years and now find myself in Knoxville, TN.
What’s the title of your screenplay?
“Calamity Jen”
What’s the logline and how did you come up with the concept for your screenplay?
“A dark comedy about an actress who joins a touring theater troupe in a lawless, climate-ravaged, post-apocalyptic America.”
The germ of the idea came from a story arc on “Game of Thrones,” when Arya Stark tags along with a travelling theater troupe. As a long-time actor with a degree in musical theater, I remember thinking to myself, “Well, if I were ever transported to medieval times, at least there’d still be auditions.”
Then the pandemic hit, and theaters everywhere began closing down. But despite the devastation to the arts community, there has also been resilience. As shows were cancelled and theaters shuttered, artists continued to find ways to create. It wasn’t more than a few weeks after the country shut down that I got my first invitation to attend a Zoom play. And with a wry smile I thought, “Man, even in the apocalypse, theater folks would still be trying to put on a show.”
And thus, “Calamity Jen” was born.
Tell us about your history as a screenwriter. Where did your journey begin?
My first real step as a writer came in seventh grade. I was chosen to be part of a writing program for young playwrights at The Kennedy Center in Washington, DC, and one of my short plays received a staged reading at their Theater Lab. (I got a short write-up in Seventeen magazine; a then-unknown Cameron Diaz was on the cover. It was cool.) That led to an interest in theater, which led to me attending The Boston Conservatory as a musical theater major, which led to me moving to New York to be an actor, which led to eighteen years of misery, rejection and despair.
As a way to stay engaged with my own creativity during those long stretches as an actor where I was, as the euphemism goes, “between jobs,” I got back to writing. One of the first plays I wrote won a high-profile contest and was ultimately published by Samuel French.
The biggest royalty check I ever received for that play was $300. I started thinking maybe I should give TV a try.
What motivates you to be a screenwriter or filmmaker?
Despite my background in theater, my true love as a consumer is TV. I grew up on TV. It was the great Gen-X babysitter. I still love it.
Theater is the best training ground I could have asked for as a dramatic storyteller, but it’s not where my passion lies. If the past year has taught us anything, it’s that life is not just short, but unpredictable. I don’t know if I’ll ever be able to make headway as a television writer (the odds are, shall we say, less than great), but I don’t want to find myself looking back when I’m old(er) and gray(er) and asking why the hell I didn’t at least take my shot.
What is the biggest challenge you have encountered as a screenwriter and filmmaker?
Creatively, it’s making the switch from aural storytelling to visual storytelling. When you write a play, you want it to be heavy on dialogue with minimal stage direction. Screenwriting is the opposite; you want to lay out the visual elements and keep the dialogue as economical as possible.
My first draft of “Calamity Jen” read like a play. The heavy lift on subsequent drafts was ripping out huge chunks of that dialogue and letting the action and the imagery tell the story.
What’s the most important thing you want audiences to take away when watching your films or reading your screenplays.
First and foremost I want them to be entertained. The main question I ask myself when writing a story is, “Is this something that I would want to watch?” If it isn’t, there’s a good chance I’ve veered into pedantry.
If it is something I would want to watch, well … then I can just go and be as pedantic as I damn well please, can’t I? But the entertainment part comes first.
Ideally, where do you see yourself in 5 years?
Ideally? Running my own show. Realistically? If I could get a slot as the tenth man in a ten man writer’s room I would be grateful beyond expression.
What’s your favorite film of all time? If you can’t single out a film, give us your top 3.
My tastes are constantly evolving, so it’s difficult to nail down a single favorite. The movies that have stood out to me the most over the past twenty years would be “Lost in Translation,” “Up in the Air” and “Spotlight.” All three of them have such a beautiful, understated quality that I find myself drawn in viewing after viewing.
That said, if “Blazing Saddles” is on, I’m watching “Blazing Saddles.”
What’s your earliest favorite childhood movie?
So, one of the facets of growing up Gen-X is that we were allowed to watch movies that were wildly inappropriate. At six years old, I saw “Airplane!” in the theater. It’s still one of my favorites.
Who’s your favorite cinema hero?
Weird answer here, but I’m just gonna go for it: Buster Moon, from the animated movie “Sing.” His relentless optimism in the face of ongoing and abject failure is something I aspire to.
Who’s your personal hero?
Melvin R. Batten. He was the music teacher at my high school. He changed my life.