“Chicken, fish, or beef. Ya know?”
Offbeat and uncomfortable in its characterizations of four New York City residents overcoming and succumbing to their secrets, Robert Glaudini’s Jack Goes Boating makes it to the big screen. Based on his Off-Broadway hit, star Philip Seymour Hoffman enlisted the playwright/actor to adapt the work into a screenplay and thus make his directorial debut. Three of the four principals partake in the transition—John Ortiz, Daphne Rubin-Vega, and Amy Ryan replacing Beth Cole to round out the quartet—and they deliver some amazing performances. Deeply entrenched in their roles, all of which are troubled beings searching for answers in the world, the actors are complemented nicely by Hoffman’s keen eye and strength of vision. With a stunning soundtrack containing the likes of Grizzly Bear and Fleet Foxes, one cannot deny the flashes of brilliance in a few gorgeous montage sequences set to the indie tunes. The success in aesthetic and acting, however, never overcame the awkwardness I felt delving into the private places we go with these four—for the lack of a better term—strange people.
The whole experience of watching this film has left its mark because of how torn I am in my digestion of it all. If I truly found the acting to be top-notch while the actual characters themselves off-putting, doesn’t that mean the odd feelings cultivated are what the filmmakers desired? It’s as though I’m supposed to question these people onscreen and wonder what it is we aren’t shown in their pasts making them the way they are. Hoffman’s Jack is a bundle of nerves and insecurities, complete with a nervous throat clearing sound when apprehensive. Shy to a fault, he cowers in the face of a public identity, working as a limo driver for his uncle and constantly wearing headphones—attached to a cassette player no less—when able. There is a sense of pity in the way his best friend Clyde (Ortiz) and wife Lucy (Rubin-Vega) interact with him, leading us to believe he either has a mental problem or a horrific past emotional trauma at the center. Either way, his eccentricities make Jack a perfect candidate for dating Ryan’s Connie, a woman also riddled with societal handicaps.
There is a childlike sense of naivety to the world in both despite being in over forty and without relationship experience. You will smirk at Connie’s over-active imagination and belief any man who touches her is making a sexual advance—until tragedy does strike. You’ll be charmed by Jack’s quiet moments, pumping up with reggae music to find the courage to talk to Connie, someone he truly likes even though their first date was a steady stream of ‘why is she telling him this?’ stories of her parents’ deaths while he winced and repeated “God” in response. It is a study in anthropology just to watch the two of them interact as they use such literal language, appear to have no filter to their emotions, and seem the problem cases in comparison to Clyde and Lucy’s idyllic couple hoping to give Jack something in his life besides the three people in his heavily constricted circle. These introverts are stuck in menial jobs, acting as though one step out the door is an insurmountable mountain to climb while their friends are successes, in love, and trying to spread their joy.
However, in Jack Goes Boatings most intriguing turn, Glaudini slowly unearths how the insecurities of two become barricades allowing them to candidly share what they want from one another while the strength of the others is discovered to merely mask severe fractures pulling them apart. Living with their own brand of trust issues, Clyde and Lucy look to give Jack advice as a way to project what they want from their relationship onto him and his. We see the repressed feelings behind their smiles, Ortiz’s anger bubbling to the surface when volunteering to teach Jack how to swim in preparation for a future date with Connie aboard a rowboat—the act of those lessons bringing up memories he’s tried hard to forget. It’s easy for Clyde to proclaim love for his friend since their bond is solid, but he does so in lieu of realizing he may not feel the same about his wife. Everything Jack needs to woo Connie runs parallel to the details surrounding a past transgression of Lucy’s; watching love blossom before their eyes only helps show how distant the married couple has become, no longer able to just ‘live with’ their mistakes.
Violent outbursts and drunken errors in judgment follow as everything implodes. One couple only knows how to lie while the other finds expressing the truth to almost be too difficult. Rubin-Vega is great as the woman relegated into the ‘villainous’ role, overcoming it by giving her humanity despite what she has done to alter the landscape of her marriage; Ryan’s innocence somehow never crosses the line into absurdity, although flirting closely; and you can’t help but empathize with Hoffman’s Jack as he stumbles along trying to better his professional and personal lot. He succeeds in the moments of quiet introspection, doing more in portraying joy through comparing it to the depression otherwise present on his face. Everything ends up being one giant build-up to an eventual explosion as the expression of untainted companionship becomes too much to bear, laughing in Clyde and Lucy’s face, inside their own home. And, as a result, it is Ortiz who steals the show as he wrestles with overcoming his demons to help a friend. Jack may go boating with a girl he’d have been too afraid to approach on his own, but it’s Clyde who is ultimately in need of a release from his own self-induced, trapped existence.
 Philip Seymour Hoffman directs and stars in Overture Films’ Jack Goes Boating. Photo by K.C. Bailey © 2010 Big Beach Films, LLC and Overture Films, LLC. All rights reserved.
 (Left to right.) Amy Ryan, John Ortiz and Daphne Rubin-Vega star in Overture Films’ Jack Goes Boating. Photo by K.C. Bailey © 2010 Big Beach Films, LLC and Overture Films, LLC. All rights reserved.
 Philip Seymour Hoffman stars as Jack and Amy Ryan stars as Connie in Overture Films’ Jack Goes Boating (2010)