Doc NYC preview: ‘Five Weddings and a Felony’

Realscreen chats with first-time director Josh Freed about his highly personal doc debut, premiering at Doc NYC this Saturday.
November 4, 2010

The inaugural DOC NYC film festival will take over New York this weekend featuring a program that mixes films by icons of the genre such as Errol Morris and Werner Herzog, with highly-personal shoestring efforts.

One film that fits in the latter category is Five Weddings and a Felony, a lively and intimate first-person confessional about first-time director Josh Freed’s confusing quest for a meaningful relationship. The doc will have its world premiere at DOC NYC on Saturday, Nov. 6 and screens again on Nov. 9.

Freed began shooting the footage that would become Five Weddings and a Felony to impress a woman he was trying to date. A graduate of Columbia University’s film program, Freed interned for filmmaker Barbara Kopple and later landed a job in 2007 as an associate producer on Very Young Girls, director David Schisgall’s documentary about child sexual exploitation in the United States. When production on that film ended, he continued working with Schisgall, producing web videos for Vanity Fair and editing an episode for the PBS’ news show Frontline.

At the same time, he was filming his burgeoning courtship of a woman named Katja, who, we’re told in the film’s accompanying narration, had written a screenplay with a big-time director and experienced the type of success in the film business that had eluded him.

When the relationship ended a year later in 2007, he turned his lens toward two friends who were planning to marry, Adam and Liliana (an Orthodox Jew and a devout Catholic), in hopes of restoring his faith in romantic love.

Around the same time, Schisgall began writing a screenplay and didn’t have any work for Freed. So, the aspiring director pitched the idea for a personal documentary about the trials and tribulations of his courtships. The producer liked the idea and provided Freed with a camera and enough financial support to allow him to sub-lease his apartment in New York and move in with his parents in Chicago to work on the film.

‘I think I had to make it because all these exes were getting married and I felt like I wanted to understand how they got to that point that was so far beyond me,’ says Freed.

In May, 2009 the film became a full-time project. He filmed his trips around the country to his friends’ weddings, and documented both a budding long-distance relationship with Liliana’s shy younger sister Paulina, and flirtations with old flames he’d find himself on the dance floor with various receptions. All the while, Freed’s constant existential self-questioning proved a seemingly insurmountable barrier to his own happiness.

When he returned to New York with the footage, Schisgall liked it and agreed to pay him a small salary to finish the film. ‘He was excited by the intimacy and the tenderness of some of the moments,’ he says. ‘There’s a scene in the kitchen with Paulina where we’re talking and I’m jealous and she looked at me with this tenderness. And I remember him telling me, ‘You know that look? You spend a lot of money and a lot of time trying to get an actress to give you that genuine look on camera and you got it right there.”

Freed shot half the film on a Flip cam and the other half on a few different high-def camcorders such as the Sony HVR-V1U HDV. By the time he was finished, he had 200 hours of footage, which he cut and re-cut with Schisgall providing advice not only as a producer, but as extemporized psychoanalyst. ‘Some times I would put a different scene in and he would have an insight into what was going on in a scene that I hadn’t seen in the same way or consciously understood,’ says Freed.

One problem inherent in the first-person diary film is the camera’s impact on the unfolding drama. Several times, his friends, girlfriends and family members would question the authenticity of his behavior in the heat of the moment, but Freed insists he never did anything for the sake of a good scene.

‘[The camera] does take your attention away a little bit and it’s hard to fully be in that moment,’ he admits. ‘But I think as I got used to it and my subjects got used to it, it got easier.

‘Finishing this film was a very important step,’ he adds. ‘Even if it gets bad reviews or doesn’t get any distribution, I finished it and I feel good about the storytelling and the characters and a lot of things in it. That’s going to help me along in both my career and my life.’

About The Author
Andrew Jeffrey joined Realscreen in 2021 as its news editor. Here, he helps to oversee assignment, reporting and editing for Realscreen's daily newsletter. Prior to his work covering documentary and non-fiction film and TV, he worked as a reporter and associate producer for CBC Edmonton, and as a reporter for The Star Calgary, where he covered daily news on beats such as local and provincial politics, health care and harm reduction, sports and education. His work has appeared in other Canadian news outlets such as TVO, the Edmonton Journal and Avenue Magazine.