With his second novel completed (and rejected), Jonathan moonlights as a creative-writing teacher, while also taking on some desperate new clients in Season Two of this 'noir-otic' HBO comedy series.
Taking time out from his new gig as a night-school fiction-writing teacher, Jonathan (Jason Schwartzman) is hired by a mounted policeman (Lenny Venito) whose name is on the client list of an S&M dungeon that’s about to be busted. Meanwhile, George (Ted Danson) is flummoxed to learn that his new publisher plans to cut costs on every front, and Ray (Zach Galifianakis) fails a yoga test with Leah (Heather Burns), putting their relationship in final jeopardy.
Kenny Powers (Danny McBride) heads to Mexico to lick his wounds and start a new, more anonymous life. Befriended by a neighboring Mexican family and a sultry bar singer named Vida (Ana de la Reguera), Kenny emerges from “the darkest hole I’ve ever been in” by planning his comeback.
George worries about remaining “intact” after getting some sobering news from Dr. Kenwood (Jessica Hecht), his new urologist. A bad day for Jonathan gets worse when a pair of S&M henchmen (Domenick Lombardozzi, Jim Norton) kidnap him, demanding a ransom that calls “GI” George and Ray to action.
A professor (F. Murray Abraham) hires Jonathan to track down a valuable item. George finds an alibi to explain the results of his drug test. Flushed with cash from his “Super Ray” comic book, Ray heads to the bar – and meets a familiar barfly (Kristen Wiig).
Jonathan attempts to repair the relationship between a poet/limousine driver (Ajay Naidu) and his wife (Sarita Choudhury). Ray has a meeting with Kevin Bacon.
Leah hires Jonathan to help find her new dog, “Little Ray.” Ray joins Jonathan in the search for the dog, getting some inside help from a local woman (Olympia Dukakis). A reflective George heads to the hospital for surgery.
A dermatologist enlists Jonathan (Jason Schwartzman) to deliver a letter to his intended at an Asian health spa. Jonathan takes Ray (Zach Galifianakis) to the spa for his birthday, with George (Ted Danson) and his new chauffeur Vikram (Ajay Naidu) in tow.
In the Season Two finale, a mad stalker imperils Ray on the eve of the Brooklyn Comic Con. George decides to make a stand at work. Jonathan has another battle with his nemesis, Louis Greene.