In its simplest terms, Bored to Death is about characters who envy one another. Ray and Jonathan could never imagine George’s wealth and influence and life of indulgence, all while working within the arts (if we’re being generous about the cultural status of magazine journalism). Meanwhile, George wants nothing more than to hang onto youth and vitality and the opportunity for third, fourth, and fifth chances — Jonathan and Ray may be no one’s idea of vigorous physical specimens, but they’re decades younger than he is, trying to make their way in the city on the backs of their creative talents. It’s not a mean-spirited envy, it’s more the grass-is-always-greener variety.
To that end, George and Jonathan vow to no longer let their pessimism get the better of them. George feels he has more reason to be feeling blue, what with the cancer diagnosis, but Jonathan, who doesn’t even have the writing chops or C.V. to get an adjunct professorship, starts musing aloud about applying to law school — a form of death of its own. George’s speech about not wanting to be turned off is a beautifully written slab of melancholy that counters the rest of the episode’s seventies-gumshoe high jinks.
Jonathan is hired by a literature professor at Midwood College (F. Murray Abraham!) to steal back a signed copy of On the Road that he unwisely used to pay off his heroin dealers. This teacher, who had one novel of note in the seventies and could never get it together to follow it up, represents a new option for Jonathan as he visualizes the abject failure his life is becoming. “You come in a queer package,” he tells Jonathan, “but you’ve got guts.” (He also wonders why Jonathan isn’t writing about his cases, which makes two of us.) Making matters worse, Louis Green is on the campus to provide some smarmy taunting and can’t fight the temptation to trail Jonathan as he follows the teacher’s dealer back to his lair. (It is a testament to the simplicity of the real Jonathan Ames’s worldview that he depicts heroin dealers in 2010 as having a lair, complete with street-level windows through which an aspiring detective and a weasly literary critic can observe all manners of contraband being sorted.)
Of course the dealers notice these spies, and make Louis do cocaine to prove he’s not really a cop, despite the poor man’s nasal polyps, and Jonathan uses the moment to make an escape in a cloud of white dust, book and enormous bag of weed in hand. The dealers chase Jonathan and Louis through ... the inner-city woods — again, best to not think too hard on the practical details — and Louis falls and hurts his ankle. Rather than leaving his nemesis to the wolves, Jonathan fights off the completely unarmed narcotics dealers with a tree branch like a ninja in a trench coat.
While Jonathan and George contemplate their downward spirals, Ray is on something of a roll. His self-published SuperRay comic is actually selling and makes the nerdy girls with elf ears get all squishy. He picks up Kristin Wiig’s Carol and brings her home, which allows for the possibly ad-libbed piece of genius, “I want to go down on your beard.” (Another great Ray exchange: “Where do you get your ideas?” “I smoke pot and then I draw.”) Thanks to the power of positive visualization, Ray is the only one of our three heroes who’s finding some success, and no one quite knows how to handle that.
That’s not exactly true — Jonathan envies that attitude and vows to try it himself. He excitedly reenacts the battle to George in his impossibly spacious Maritime Hotel suite. George, who has just failed Wellstone’s mandatory drug test, gets out of a rehab banishment to Arizona by telling Catherine about his prostate cancer. So even he has found a silver lining to his black cloud. Bored to Death’s main characters are broad, sure, but they’re likable enough that these little reversals of fortune feel like proper drama, and fuel enough to keep the show’s relatively rudimentary engine running.