Neurotic writer turns romantic P.I.

Ever since he burst onto the book scene two decades ago with I Pass Like Night, the story of a young college grad’s descent into New York’s sleaziest corners, Jonathan Ames has been one of the city’s quirkiest—and most autobiographically minded—literary fixtures. Comic novels such as The Extra Man and Wake Up, Sir!, essay collections like this summer’s The Double Life is Twice as Good, graphic novels like The Alcoholic, and occasional ventures into one-man shows, stand-up comedy and bizarre performance art, all tap into Ames’s primary obsessions: neurosis, masculinity (or lack thereof) and situations that would be embarrassing to most, but when Ames or his fictional alter-egos experience them, come off as endearing. How else to explain the standing-room-only crowd packed into a Brooklyn gym two years ago to see Ames engage Canadian writer Craig Davidson in a boxing match—and win?

But now the 45-year-old Brooklyn-based writer is about to reach a much broader audience. A film adaptation of The Extra Man, featuring Kevin Kline, John C. Reilly and Katie Holmes, has just wrapped production. And as of Sept. 20, TV viewers will get to know Jonathan Ames—or rather, his fictional counterpart “Jonathan Ames,” as played by Jason Schwartzman—in HBO Canada’s new eight-episode comedy series Bored to Death, created, produced and mostly written by Ames and based on the darker short story of the same name.

Within 20 minutes of the pilot, “Jonathan” morphs from a commitment-phobic struggling novelist and magazine writer recently dumped by his girlfriend Suzanne (Juno’s Olivia Thirlby) to an unlicensed PI on the lookout—with suitably disastrous and cringe-comic results—for the missing sister of a college co-ed who saw his ad on Craigslist. The impetus? A frayed paperback of Raymond Chandler’s 1940 novel Farewell, My Lovely, Ames’s favourite Chandler novel. “Marlowe’s the most romantic of private detectives out there,” said Ames, speaking by telephone from Los Angeles, “and he’s someone a young man would want to emulate more than, say, the Continental Op,” the tougher, far less handsome detective created by Dashiell Hammett, another of Ames’s favourite crime writers.

Watching “Jonathan” attempt to right wrongs such as cheating boyfriends and missing screenplays certainly rings with Chandlerian echoes, but two other people—one obvious, one less so—came to mind. “Jonathan” is not the author, but there are distinct mannerisms of the real article that creep into the character, from the crinkling of his eyes, the set of his mouth and the flattening out of his accent. “I didn’t consciously set out to ‘do’ Jonathan Ames,” said Schwartzman from his home in L.A., “but I moved back to New York a month or so before shooting the pilot, and I would shadow [him] a little bit in order to get a sense of his Brooklyn—his streets, the coffee shops where he’d work, the bars—and merge it with the dreamed-up version in the show.”

But the detecting MO “Jonathan” employs also owes a tip of the hat to a certain comic icon made famous by Peter Sellers. “Certainly, Inspector Clouseau came to mind—the slapstick, the fumbling—but [“Jonathan Ames”] is not as dim or as blind as Clouseau,” Ames clarified. “Most of his fumbling comes from his inexperience and the interjection of his own struggles into the cases. He’s a flawed knight doing the best he can.”

Each episode uses a particular case as its narrative framework, but Bored to Death is just as much about what executive producer Sarah Condon dubs “the three stages of man”: “Jonathan,” the often-thwarted white-knight optimist; his best pal Ray (Zach Galifianakis), a scruffy cartoonist in a passive-aggressive relationship with his live-in partner, and his magazine boss George, given dissipated glamorous life by Ted Danson sporting a shock of white hair and a knowing sense that his type of man has become an anachronism.

Time will tell how Bored to Death will be received by the masses, but Ames is as sanguine as he could be about whether the show’s audience will be entertained by his particular brand of neurotic New York comedy. “HBO has a very literate audience—it’s not like it’s a sitcom for ABC, which would be a real leap,” he laughs. And as for the experience of moving from writing prose to creating a television show out of wholesale cloth, “it’s like being handed the keys to a Ferrari without ever having driven a Mustang before.”