New York City Serenade tells the story of lifelong friends Owen and Ray and the series of events that lead to their final farewell. A simply told, surprising and emotional film in the tradition of Mike Leigh, Paul Mazursky and Ken Loach, New York City Serenade follows in the spirit of Frank Whaley's earlier films Joe the King and The Jimmy Show telling a riveting human story without compromise, with humanity and heart.
The film follows Owen and Ray. Owen is an aspiring filmmaker, suffering in a job as a photo developer at the neighborhood photo shop. The one good thing in his life is his relationship with his fiancée, Lynn. Owen’s childhood friend, Ray, is a struggling musician who works as a telephone salesman in order to support himself.
One night Ray invites Owen and their friends Terry and Russ to a house party in the city. Rachel, an attractive Columbia co-ed, seduces Owen, while Ray gets involved in a game of truth or dare with several girls, not knowing one of the girls’ brother is throwing the party. When the brother and his jock friends burst in on Ray’s game, chaos ensues and Ray, Owen, Terry, and Russ are chased from the party.
The World Wide Film Festival has accepted Owen’s short film and gives him two first class tickets to the festival. Owen is excited to share his moment of glory with Lynn, but that excitement is abruptly extinguished when his indiscretions catch up with him. After finding out about Owen’s fling with Rachel, Lynn breaks off the engagement, leaving Owen heartbroken.
Determined to cheer up his depressed friend, Ray steps in to accompany Owen to the festival. Things begin to look up for the two friends when they run into actor Wallace Shawn at the airport. As Owen anxiously looks on, smooth-talking Ray approaches Wallace to invite him to the screening of Owen’s film. When he returns, Ray not only has persuaded Wallace to come to the screening (or so he claims), but has also lined up a room for he and Owen at the Four Seasons (quite a step up from their reservations at the Motor Lodge). The trip seems to be going well; Owen is even approached by an interested Los Angeles sound designer. To celebrate, Ray invites some girls to their luxury hotel suite at the Four Seasons. Before the celebration can begin, hotel security arrives. Unbeknownst to Owen, Ray has been posing as Wallace Shawn’s son in order to stay in the suite. The two are kicked out of the hotel and left with the hefty room service bill. Humiliated and worried about his fragile reputation as a filmmaker, Owen is furious with Ray. His escalating frustration leads to a fight that ends with Ray locking himself in the motel bathroom. In the morning Ray is gone.
Unable to face the heartache and loneliness that await him in New York City, Owen impulsively exchanges his return ticket to New York for a one-way ticket to Los Angeles.
Eighteen months later, after moderate success in LA making commercials, Owen is back in New York City. Out of a cab window he glimpses a clean-shaven Ray sitting on a park bench. The two friends are happy to see each other, and their reunion is a warm one. Time has treated both men well and their anger has faded into the past.
It is apparent that sometimes to keep a friend you have to grow up and grow apart.