New York City Serenade

[StevePulaski]

New York City Serenade (2007)
Directed by: Frank Whaley

Freddie Prinze, Jr. and Chris Klein in New York City Serenade.

Rating: ★★★½

With three directorial efforts under his belt, and a fourth one on the way, from the looks of it, actor Frank Whaley seems to love to explore the ideas of good people making bad decisions in situations where they are simply trying to do the right thing. In his directorial debut Joe The King, Whaley focused on a young adolescent, who had been emotionally neglected and physically abused by both his parents, but carried an undying love for them, so much so that he stole and deceived others in order to better off their situation in a surprisingly captivating take on the idea of an anti-hero. In his sophomore directing effort, The Jimmy Show, we saw Whaley play a man struggling to maintain a marriage, hold down a job, raise a child, and take care of his elderly grandmother, all the while trying to carry out a standup comedy career when he wasn't just not funny but wholly depressing and upsetting.

Whaley's latest film, New York City Serenade, is a film that catches one off guard, allegedly masquerading as a frothy, incredulous romantic comedy but existing as a thoughtful and realistic iteration of two lifelong best friends realizing that they are each others dead-weight in the middle of a potential break for one of them. The film stars Freddie Prinze, Jr. and Chris Klein, two actors we never really got to see in captivating roles until now. Prinze, Jr. stars as Owen, an aspiring filmmaker who's short film has just been nominated for an award at a small film festival. Owen agrees to take his longtime girlfriend and now fiancee Lynn (Jamie-Lynn Sigler) to the festival as his sole guest, which will be held in Los Angeles. However, when Owen listens to his longtime buddy - the heavy drinking Ray (Chris Klein), who plays in a band - and goes to a party, cutting his movie-date short with Lynn, he winds up cheating with a woman at the party, leading Lynn to break up with him just before the festival.

Ray tags along on the trip from New York City to Los Angeles, much to the dismay of Owen, who wants to be left alone. The idea of both men being dead weight to each other comes in when we see that all Owen wants to do is have a quiet evening, which is impossible with Ray, who slugs cheap vodka shooters endlessly, and we see all Ray wants to do is be belligerent and disrupt the consistency of a formal event. Ray winds up impersonating the son of director Wallace Shawn, and gets the two a lavish suite at The Four Seasons, leading Owen to recognize that this friendship and his own career will not thrive if both kept around and that one needs to be terminated.

Prinze, Jr. and Klein carry on a great chemistry in this film, and their characters are incredibly similar to the likes of Dante and Randal from Kevin Smith's Clerks, whereas each character is flawed or burdened by an unlikable characteristic in a pretty significant way, but we still can't help but root for them, or at least find them interesting in some way. While Owen's actions are pretty offputting, and nearly everything Ray does is in poor taste and contemptible, there's a certain beautiful realism in their conversations, biting relatability in their friendship, and true honesty in the way they communicate and vent their problems to each other, which will undoubtedly remind people of that friend they have in their life - the one that means well, is fun to have around for a while, but also does things that are truly unforgivable and grounds for termination on someone's metaphorical friends list.

There's the relatability, and Whaley's human interest that makes New York City Serenade surpass any preconceived cliches it could've had under its belt. Whaley, who makes a cameo himself and allows a poster of his preceding film to be used in a key scene, if you pay close enough attention, clearly has a fondness for characters burdened or flawed in serious ways, making them the protagonists of each of his first three directorial efforts. This allows for a sense of reality to buoy the picture, rather than a ridiculous and frothy sense of romanticism or contrived relationships. At times, Prinze, Jr. and Klein's relationships tread so close to real life they cause an abrupt sense of pain.

New York City Serenade may find criticism for profiling two rather contemptible characters, but in the end, everyone is contemptible in their own way, and the fact that Whaley allows his characters to lay their cards out on the table from the start, showing some of their worst traits (Owen's whiny attitude and momentary infidelity and Ray's obnoxiousness and complete lack of sympathy or empathy towards anyone) to be seen deserves some credit, especially considering he takes two good-looking, male actors - one of them known for their pretty boy roles - and makes their characters' personalities and quirks ugly and noticeable. After three thoroughly commendable films, I demand Whaley writer and direct more films this instant.

Starring: Freddie Prinze, Jr., Chris Klein, and Jamie-Lynn Sigler.