This case of Jonathan's was one of the first I conceived for him. Initially, 'Bored to Death' was going to be a novel in three parts. The first part was to be the original short story; part two would be incarceration as a result of part one and I could act out, through my writing, my fascination with imprisonment; and in part three, Jonathan would get out of prison and become a full-time detective. (For great prison novels, I recommend the work of Eddie Bunker, whom I met once in Mexico, which is another long story.)
So the case of the blackmailer was a case that I was going to give Jonathan in the novel after I read about a husband-wife blackmail team in the New York Post, who were perpetrating the same kind of blackmail that we see in the episode. By the way, isn't blackmail an interesting word? I don't have time to research the etymology and the birth of that word, but since most blackmail begins with a dark and ominous letter, some journalist for a London newspaper in 1850 or so must have invented the word for a scandal that was going on, or it probably goes back to the Sixteenth Century, since it seems like Shakespeare would have used that word...Anyway, for people who are nuts about etymology I highly recommend Simon Winchester's book about the Oxford English dictionary - The Professor and the Madman.
Anyway, I never wrote the novel, but I did create the TV show, and so I still had the case in mind. When I was looking for writers, I mentioned to Martin Gero, whom I eventually hired to be a writer on the show, that one of the cases I would give Jonathan was this blackmail case where Jonathan would sleep with the blackmailer, and he suggested that this would be a good opportunity to get all three guys involved in a case and I thought that was a smart suggestion, and hence Martin came on the staff. Thank you, Martin!
One of the scenes that was most beautifully actualized for me during the whole season is the opening shot of Jonathan emerging from the Subaru at the diner in New Jersey. Adam Bernstein, our director that episode, seemed to go right in my brain and perfectly paint what I wanted, which was a slow-motion, super-cool shot of Jonathan emerging out of the car like a hero, and Adam pulled it off perfectly. Thank you, Adam! He took the description in the script and really made it come to life. And thank you, Jason Schwartzman for looking so amazing and cool in that moment! I want to be a hero in the worst way, and so that shot was total wish-fulfillment for me...
Once we're in the diner, Geoffrey Cantor is brilliant as Mr. Eaton, the beleagured father of two. A month or so after we shot this episode, a strapping, attractive, and rather hip looking fellow came up to me at the wrap party for 'Bored to Death' and was very familiar with me. The gentleman seemed to know me quite well, but I didn't know him or remember where I had a met him and I confessed this. Well, it turned out it was Geoffrey Cantor - the guy had completely transformed. He wasn't the humbled and humiliated Mr. Eaton at all. He was a ladies man who looked to fare very well at the libidinous wrap party. I complimented him on his abilities as an actor to completely, like an Alec Guinness, transform himself. Thank you, Geoffrey Cantor!