(2010) Reprising his stage role for the screen, Philip Seymour Hoffmann portrays Jack and directs the small cast in this "dromedy" of misfits from playwright Bob Glaudini's script, adapted from his own play. A middle-aged limo driver in Manhattan, who lives in his uncle's basement, Jack, wearing his stringy blond hair in dreadlocks and listening to reggae music on his headphones, timidly agrees to meet a woman for dinner his best friend and fellow limo driver Clyde (John Ortiz) introduces to him through his wife Lucy's suggestion.
During the meal in Clyde's apartment, Connie (Amy Ryan) tells Jack and Clyde about being with her comatose father where the male coma nurse came on to her, just before Lucy (Daphne Rubin-Vega) arrives with chunky-monkey ice cream. While walking her to a cab afterward in the snowy night air, Jack, in child-like innocence awkwardly struggling at speech, hears her suggest they go boating together sometime before Connie gives him a kiss on the side of his face.
But he can't swim Jack tells Clyde, who takes his buddy to an indoor pool in Harlem and teaches flabby Jack to swim. In Jack's eyes, Clyde (who's attending night classes to improve his opportunities) in his marriage to Lucy has a well-formed relationship as desirable as the physique of a man he sees in the locker room until he realizes the man's missing his legs.
At work Lucy became acquainted with Connie, hired to solicit customers over the phone for Dr Bob's grief seminars, but though pitying her social ineptitude, Lucy decides to fire Connie for failing to complete a single transaction; Connie arrives bloodied from being sexually assaulted on the subway and still manages to close a deal with a client before going to the hospital with a broken nose and fractured ribs.
Jack, following his Uncle Frank's instructions to get a gift, arrives with a stuffed koala bear and then offers to cook her a feast when she's well. "No one has ever done that for me before," Connie expresses her gratitude.
But he can't cook Jack confesses to Clyde, who arranges for his pal to get culinary lessons from Federic, a chef at the Waldorf-Astoria. Lucy has a connection with the "Big Cannoli," Clyde explains (warning Jack never to make mention of any of this), from a "thing" they had together, as well as another with a charismatic "death guy, grief expert" in an elevator ("only kissed him," she'd said): "That's what you live with - never knowing for sure."
After Jack accidentally spills the beans to Lucy, she fills him in on Clyde's many failings along with a caveat for him if he's in a long-term relationship: "Things will come that you'll have to live with." Following Clyde's having taught him to mentally practice swimming by visualizing the strokes first, Jack sees himself plowing through a liquid lane of traffic beneath a bridge; he does something similar in thinking through preparing a meal for Connie.
Having invited him up to her room and in bed with her, Connie (though she's imagined doing it with him in the bath) informs Jack: "I'm not ready for penis penetration." Nevertheless, enjoying his light, stimulating touch, she asks him what he expects in a woman. Someone with a positive personality who appreciates music, but who doesn't need other men to satisfy her. "I won't do that, ever," she assures him before answering the same question from him with wanting a man to be truthful, humorous, employed, patient, gentle, and sexy (which she generously says he is).
At Lucy and Clyde's Jack proudly prepares his feast for Connie while Lucy brings out a hookah with hashish and Clyde departs for a walk (meeting Connie as she's coming up), saying he wants to work up his appetite. When Clyde comes back as they're enjoying a toast of sweet smoke, a moment of paranoia envelopes them when the phone rings, the door buzzes, and all hell breaks forth. The soundtrack and especially "Rivers of Babylon," a song on Jack's tape player, at times become like another character's dialogue.
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