How to Open a Window When Your Entertainment Career Door Slams Shut

How to Open a Window When Your Entertainment Career Door Slams Shut

I’ve always considered myself unsuccessfully successful.
On paper it all sounds pretty great.
I started writing movies out of the angst of being a struggling actor. A casting director may not choose me. But I can. I choose me. The first movie I wrote had Chevy Chase and Burt Reynolds, Not Another Not Another Movie. My second, Scouts Honor, had Fred Willard and Chris Kattan. I then directed a passion project I wrote about a musician who gave away millions to live on a Native American Reservation, named Rich Mullins.
The movie was called Ragamuffin.
It was very underground. Our theatrical distributor was two guys in a Toyota Corolla. We did ragtag screenings all over the country in movie theaters, bars, and coffee shops.
We did 208 screenings and pulled in about 300K and eventually signed a distribution deal with Millennium Entertainment and they grabbed us an exclusive with Walmart and the movie eventually landed on Netflix for a few years.
Me and Chevy Chase on set of "Not Another Not Another Movie"
And guess what I do now to pay the bills? I drive for Uber.
Matter of fact I once had a big time manager fire me for writing an article in the Hollywood Reporter for joking about being a rideshare driver. “As an actor you might have seen me in such hits as your Lyft driver.” He was embarrassed. But not as much as me. It’s okay though, we’re still friends.
I’ve always valued authenticity.
The truth is, I’ve always wanted to be an actor.
Period.
But I knew pretty quickly that the chances were slim. When I moved out to LA in 2004, I told myself - I want to figure out how to do this for the rest of my life, even if I never scratch the winning lottery ticket.
Friends…I’m still scratching.
I started writing movies for myself to act in. The problem was I didn’t know how to write. My background was as a sketch comedian with the hopes to one day be on Saturday Night Live. I had some nibbles of interest there and even got close to being a cast member on the last season of Mad TV back in 2008.
Close…but not close enough.
Poster for "Ragamuffin"
I remember the first screenwriting book I ever read was after I made those first two movies. Whoops. I’ve always been the type of person to dive into the deep end and then start learning how to swim.
But the writing wasn’t the only problem why my first two movies failed. Would you imagine I had some pretty shady producers involved who messed up both those projects? Hard to believe, I know.
Down in the dumps, a dear friend told me, “Make one more movie…but this time you be in charge.” And that movie was, Ragamuffin. I’m sure you haven’t heard of it, but I hear it’s helped a few people. It’s even saved a few lives with reports of folks who struggle with suicide finding hope and light in a world that’s often dark and depressing.
But even after 7 movies and an almost acting career that can never seem to get off the ground, I mean…who needs another chubby white guy anyway? Most agencies have that type covered.
So what do you do when it just feels like it’s NEVER going to happen for you?
You keep going.
One foot in front of the other. That’s what I have to tell myself each and every day. Get better at acting. Keep sharpening my comedic point of view. Keep writing. Keep learning. Fill the page. Re-write the page. Rest. Then do it all over again.
But after awhile, when you think you’ve exhausted all the referrals, opportunities, classes, and trope advice…you just start to lose hope.
Just being honest. It’s called, “Breaking-In” for a reason, right?
B.J. Bales, Fred Willard, and Myself BTS of "Scouts Honor"
But for well over 15 years I have felt it’s just unbreakable. And it’s hard to hold on to hope when your friends either give up or become famous. You, the one that hasn’t given up, starts to feel stupid.
You question whether all those people, even from movie stars and powerful executives, that say “you’ve got it, just keep going”…are just pandering because they don’t have the heart to tell you that there is no lottery ticket coming your way.
And that’s the truth. There is no lettering ticket. Out of despair I often, metaphorically, find myself sitting on a bus stop, waiting for the bus of opportunity to come.
But that bus ain’t coming. You have to go and find that bus. And sometimes you have to go build your own bus.
I’ve built my own bus. Several times. And they’ve all broken down.
And in the midst of my mid-life crisis and mounting despair, if I’m honest…I’ve been thinking of quitting. Matter of fact I probably think about quitting 27 times a day (and still do).
But a few months back…in the midst of the script beat of my life called “All is Lost”…and trudging through the “Dark Night of the Soul” …there enters an unlikely mentor, a guiding light, called Stage 32.
I don’t even know how I discovered it. Probably an ad on Instagram.
But as soon as I discovered the platform - I thought, “This is too good to be true.” I called my screenwriting buddies. Some had heard, some haven’t…but the reputation was firm that “they were one of the only good ones.”
So I thought I’d give it a shot and it has turned out to be the best decision of my career so far.
Not just because of opportunities, but because of something better.
Hope.
Me and Burt Reynolds in "Not Another Not Another Movie"
After 17 years of feeling beat-up and burnt out, Stage 32 finally feels like a true gateway where you can let your work speak for itself. And have the space for grace and humility to make it better. It truly feels like the first democratic bridge, door, gateway, or whatever metaphor you want to use, that will actually give you a window (damn… pick a metaphor and stick with it David!)…into making your Hollywood dreams come true.
To say that I’m thankful for Jason, Amanda, Angela, Taylor and the whole Stage 32 crew is an understatement.
For example, Carli Haney, was so encouraging, insightful, and brilliant…it has helped elevate my projects. (Thanks Carli!). And that’s just one example.
All of the executives, writers, reps, and especially the staff of Stage 32 have given me hope.
Now I have to go. I have to go drive Lyft.
Pursue your pleasure.
Find your joy.
Always be a student of the craft you are craving.
Don’t worry about the success or the failures. Just keep one foot in front of the other. Fall off the horse and get back up…(Dammit here I go with the metaphors again).
You get what I’m saying. If this work, that we all love, this world of storytelling, is what brings you life. Do it, not because you’ll be famous, rich, or successful, do it because you are alive and it brings you life.
And if it brings you life, then through your art, it will bring others life.
Thank you Stage 32!
About the Author

David Leo
Actor, Screenwriter, Filmmaker
David is an Actor, Writer, Filmmaker with 7 produced independent feature films under his belt. For writing he has studied under Brian McDonald and Anne Beatts. For acting under the Michael Woolson Studio and comedy with Groundlings, UCB, & I.O. West.