Smooth sailing

Philip Seymour Hoffman delivers an emotionally honest indie romance

Jack Goes Boating
Studio: Relativity Media
Rated: R
Cast: Philip Seymour Hoffman, Amy Ryan, John Ortiz, Daphne Rubin-Vega, Tom McCarthy
Director: Philip Seymour Hoffman
WorkNameSort: Jack Goes Boating
Our Rating: 5.00

It would be so easy to dismiss Jack Goes Boating, an adaptation of the Robert Glaudini play in which Philip Seymour Hoffman originally starred in New York, as standard quirky-for-the-sake-of-quirkiness Hoffman fare: All of the Sundance-baiting elements are in place, from first-time director and star Hoffman's Jack dabbling in Rastafarianism to his desire to learn how to swim to the score by Grizzly Bear, which is peppered with tunes from Cat Power and Fleet Foxes. There's even some reliable sexual dysfunction, with Jack's love interest, Connie (the lovely Amy Ryan) recovering from a violent encounter with a subway pervert, and Jack's best friend, Clyde (breakout co-star John Ortiz), dealing with being made a cuckold by his lonely wife, Lucy (Daphne Rubin-Vega). 

But there's a massive heart within Jack Goes Boating to be dealt with before the eyes cynically roll, and it's confounding. Ultimately, the film is uplifting in a way that I haven't experienced at a movie this year. 

The people in Jack's life want only the best for him. Clyde and Lucy are emotionally intelligent and accommodating toward Jack without ever stepping into condescension. Clyde teaches him how to cook and Lucy hooks him up with a chef (who happens to be her former love) to help Jack prepare a feast for his newfound crush. Jack, unlike so many indie quirkfest's protagonists, wants to grow. He yearns to become a better person and he's willing to spend long hours doing so. In return, Ryan's Connie is patient and understanding with him. 

So where's the drama? It's a question I found myself asking as well throughout the first half, and one that's answered at a fateful dinner party, a weed-aided lovefest that inevitably serves as the setting for a variety of long-bubbling issues to boil to the surface. It's messy and often violent, but the film presents it as entirely necessary, and we believe that. Luckily, Hoffman and Glaudini navigate the terrain with aplomb, gently guiding the narrative toward genuine resolution, rather than awards-hungry theatrics. 

I can't say enough about this film's knowing sense of conflict; Jack and Connie's pivotal sexual moment toward the end is imbued with such experience and nurturing that it tells us how the filmmakers involved must have gone through their own highs and lows to arrive at such an honest conclusion. It's the first happy ending I've seen in an indie film in a very long time that feels so earned and so transcendent. 


We welcome readers to submit letters regarding articles and content in Orlando Weekly. Letters should be a minimum of 150 words, refer to content that has appeared on Orlando Weekly, and must include the writer's full name, address, and phone number for verification purposes. No attachments will be considered. Writers of letters selected for publication will be notified via email. Letters may be edited and shortened for space.

Email us at

Support Local Journalism.
Join the Orlando Weekly Press Club

Local journalism is information. Information is power. And we believe everyone deserves access to accurate independent coverage of their community and state. Our readers helped us continue this coverage in 2020, and we are so grateful for the support.

Help us keep this coverage going in 2021. Whether it's a one-time acknowledgement of this article or an ongoing membership pledge, your support goes to local-based reporting from our small but mighty team.

Join the Orlando Weekly Press Club for as little as $5 a month.