I caught that Esquire spread too. Also, I recently saw a favorable article on cryonics and immortalism in another mainstream rag, LinguaFranca. Seems like a boom of good press.
But the piece in Esquire gives me a good feel of how most people in the literate mainstream probably regard the prospect of immortality - with equal measures of curiosity and bemusement.
The Richard Dooling piece had an absurdist ring to it, mirroring the cover tag line in its inquiring "would you really want to live forever?" And the question isn't an easy one from the perspective of Dooling. In his short article, he paints a picture of a possible future that is just as frustrating, conflict-ridden, and senseless as the modern world. He projects his fictional self surviving to the year 2099 only to be killed by a terrorist in Darwin's Army, a group that opposes "unnatural" evolution.
Still, I count this as a positive representation of transhumanism. The tone may be one of world-weariness, skeptical of a better future, but that attitude just happens to be part of the zeitgeist. Anything that departs from that perspective too greatly would probably alienate Esquire's trendy readers.
Often times, for new memes to spread, they have to be packaged in a way that will mostly fall in line with what people already believe to be true about the world. By that consideration, efforts by the likes of Dooling might be far more effective vehicles for spreading transhumanist ideas than the various singularity-themed visions, which tend to confuse the hell out of most people.
If you get a chance, check it out. For kicks, there's a great photo of a twenty-something yuppie giving the finger to the grim reaper.