Meet the Filmmaker - Ryan O'Leary // The Lost Weekend

Meet the Filmmaker: Ryan O'Leary - The Lost Weekend

Ryan O’Leary is an award winning independent filmmaker from Monroe Township, New Jersey. After a successful international festival run in 2014, his first feature film, The Backseat, acquired distribution with Osiris Entertainment. The Backseat is now available on Amazon Prime and many other major digital platforms. The film picked up awards at the Manhattan Film Festival and The International Indie Gathering, as well as several other festivals.We recently had an opportunity to interview Ryan about his experiences in making The Lost Weekend, and here is what we learned.

Firstly, can you tell us a bit about the film?

The Lost Weekend is a family drama disguised as a romantic comedy. It's adapted from a feature film I've been trying to get made for the past several years called The Lost Year (yes, I am very clever with titles). After having some financing fall through, we decided to see if our investors were cool with us using the bit of money we fully secured to make a short. I try not to think of it as a proof of concept, but as something that can hopefully stand on its own and make you smile and cry at the same time.

What was your biggest inspiration to make this film/How did you get involved or attached to the project?

It's based off life experiences and the experiences of those around me.

As a filmmaker there are many ups and downs in the process, what was your absolute favourite and/or funniest part of making/producing this film?

The absolute best part of making this film was having the opportunity to work with such a special cast and crew. This was the first time where I had a producer on set who really let me just focus on directing (shout out to BBF alumni Anthony Pedone). Our casting director Adrienne Stern did a phenomenal job putting together a cast that I never thought would spend a second on material that I wrote mostly while still living with my parents. Each actor brought their own unique experience to the project. Seeing everyone work so hard made me bring up my game and simply made the film more special overall.

What does a film festival like Byron Bay Film Festival mean to you and your work?

It adds a certain degree of legitimacy that made all the more difficult parts of the process worth while. To have the chance to see the film play in front of an international audience is a dream come true and quite daunting, if I'm being completely honest. It's also an honor to be screening not too far away from where Steve Baker, one of my longtime internet colleagues, is from.

Byron Bay Film Festival showcases an array of entertaining, inspiring and thought-provoking films. Do you feel that your film helps people ‘Dream With Their Eyes Open’? And if so how?

I think it applies to Dreaming With Their Eyes Open in the sense that it gets into how sometimes we get so caught up in our emotions and little challenges in our lives, that we manage to miss what's right in front of us, and how that's often what's in our hearts and souls. Sappy, I know!

What was the most challenging part of the filmmaking process?

Financing! In film school, it was nice being able to have a crew work for free. But hitting this point in my career, everyone needs to be paid and deserves to be paid well, as I am nothing without my cast and crew.

What is the best piece of advice you can give to future independent filmmakers?

Don't be afraid to ask questions. Take your time in preproduction. Plan, plan, plan, and be ready to throw those plans away the second things start moving in a different direction. Don't give up. Be kind. Remember, we're here to tell stories. That's never something worth putting people in danger for.

If some or all of the team is coming to the festival at Byron Bay. Who is coming and what are you looking forward to?

I will definitely be attending. I'm trying to get some of my producing team and cast to go, as well. I'm looking forward to seeing how Australian audiences appreciate film and meeting filmmakers and enthusiasts that I'd never meet otherwise.

Any upcoming projects for you, your team or key creatives involved in your film?

Hopefully the feature version of this film! If anyone reading this wants to invest in a movie, I assure you, we treat our investors well!

Any upcoming projects for the filmmaking team?

Our producer Anthony Pedone is working on a doc called Chasing Chasing Amy about Kevin Smith's film Chasing Amy and it sounds INCREDIBLE. Our lead actor Sam also just got cast in an Ethan Coen play, and I could not be more excited for him.

What drives you as a filmmaker?

Life. All of it. The ups and downs. It's beautiful how it can make each experience worth having, when you know it's a story to share. Warts and all.

If you have had previous involvement or experience with BBFF how would you say it compares to other festivals or related events?

Our producer Anthony Pedone screened his film An American in Texas at BBFF and RAVED about it being the best festival out there.

Anything interesting or unique about the filmmaking process for this film, any hiccups along the way, any happy coincidences that changed the films direction?

Definitely failing to make it as a feature at first, then making it into a short.

Is anything-else you would like to share?

There's so much I'd like to share, but my laptop battery is dying and I don't have a power cable with me today. Thank you for this opportunity. I can't wait to see what BBFF is all about.

The Lost Weekend screens Saturday 19 October at 8pm and Saturday 26 October at 1:15pm the Byron Community Centre. 

You can meet many of our filmmakers at the BBFF Filmmakers Breakfast on Monday 21st October at 8:30am and other special events including the Opening Night Gala and Closing Night Gala.The Lost WeekendAfter a rough breakup, Charlie Monahan dives headfirst into the world of online dating. Guided by his charismatic best friend, Rufus, Charlie meets the charmingly complicated Maggie Mae. Quickly learning the differences between expectations and reality, Charlie's forced to confront the challenges of maintaining a relationship in the digital age. In an era where everyone's connected, Charlie's never felt more apart.