Jason Ancona Interview: ‘Dr. Cheapskate’ Director Talks About His New Film

Dr. Cheapskate is new independent comedy/drama from filmmaker Jason Ancona, set to release later this year. We recently had a chance to ask Mr. Ancona about the experience in creating the film. Read our review.

Tell us about your new film, Dr. Cheapskate.

Jason Ancona: It’s about a lonely, frugal guy, fresh off a divorce, who isn’t ready to start dating again. He runs into an old acquaintance, who becomes a friend, and who challenges him to meet women, often against his wishes.

The story feels very personal and Dana is a brilliantly realized character. As both writer and director, how did he come to be? 

JA: Thank you. And, yes, it is a personal story. I based the narrative and Dana’s character on some of my experiences. I went through a divorce, and it took some time before I had the courage to start dating again.  When I moved to Austin I didn’t know anyone and didn’t have a job. My social network started at zero. Trying to meet guy friends at forty took a while. Fortunately I did find a job after a couple of months, and after a year, ran into someone I hadn’t seen or spoken to since college, twenty years ago: Scott Dean. Who I cast as Dr. Cheapskate’s friend Beau.

In rom-com’s there’s usually a cute meet. In real life my bromance with Scott Dean started at the gym. Fortunately I had a Chicago Bears tee-shirt on and he had a much better memory than me. I recognized him, but for the life of me couldn’t recall his name. Also divorced and in his forties, we had a lot in common. We became good friends and hit the Austin social scene, often feeling like old creepy guys amongst women in their twenties and thirties. So we tried online dating to meet women who were more age appropriate. And we argued over the best way to make an online profile, where to go on dates, what to talk about, and sometimes what to wear. I always deferred to fashion-plate Scottie, with his fancy shoes and collection of infinity scarves. A lot of those experiences found their way into Dr. Cheapskate.

That said, Hunter feels like an amalgam of many kinds of rom/com ‘bad guys’, a character we love to hate. What went into developing him and his personality? How involved was actor Andrew Key in creating Hunter?

JA: Hunter’s character was drawn from a co-worker and friend of mine: A cocky, good-looking twenty-something who has no shortage of confidence and who talks a lot of trash. He’s from Oklahoma, has quite a southern accent, and is undeniably charming. And ladies love him. Women would sometimes approach him and hit on him. Was always a bit jealous when that happened. “It’s because he’s young,” Scott and I would rationalize. 

That being said, Andrew brought his personality and communication style into the role of Hunter and made the character his own. Being a cross-fit trainer, his physicality and confidence added to his performance. And he became the guy you love to hate. Andrew really did a great job.

The story takes place in and around Austin, Texas, where you currently live. What about that city attracted you to telling your story there?

JA: Austin really is a cool city. So many different things to do and places to go. The scenes with paddle-boarding, running Town Lake, and pedi-cabs show some of the fun outdoor things people do in Austin. Another great thing about Austin is that local business owners are film-friendly. Which is much different from my experience in Los Angeles, where businesses charge filmmakers an arm and a leg for using their location.

One of the really nice things about the film is its authenticity. This really felt like the right direction, especially in a sequence where Dana meets a few dates he’s met online. These women felt real and the choice to avoid a silly montage of wild or eccentric characters was refreshing. How important was it to keep this as genuine as possible and was there any discussion about avoiding rom/com clichés?

JA: You’re making my heart warm. Thanks. I tried to portray the characters as authentic. Glad you think we did. There wasn’t a discussion of rom-com clichés, but I’m sure I’m guilty of writing them in some of my previous screenplays. Think because I knew we were shooting the script, I may have had a heightened awareness about avoiding those clichés.

As an independent filmmaker, what are some of the larger lessons you learned during the process of making Dr. Cheapskate and how has it changed your approach to upcoming projects?

JA: That the people you work with, your film family, are so important. And that I am very lucky and grateful to have had a cast and crew who are such giving and talented people. Hope to work with them all again.

Another thing I’m learning as an independent filmmaker is how important promoting and marketing your film is. Without a celebrity or name actor, it’s a real challenge to get distribution, something I’m still working on. Need to improve my social media skills and hopefully build an audience for Dr. Cheapskate.

Speaking of upcoming projects, what’s next for you?

JA: The next project is Tag Team Truckers. It’s about a carefree dreamer who’s trying to figure out what to do for a living. He wants his straight-laced brother to be a part of his trucking team so they can travel the open road and work together. Before they do, the brothers test out another job to see if they won’t kill each other.

Thank you so much for your time. We really appreciate your answering our questions. Best of luck and we look forward to whatever is next from Ancona Films.

JA: Appreciate your time as well. Thanks!