He's a master of spinning absurdist scenarios into a coherent and dark lore of what is dysfunctional in the modern world. His metaphors are almost, dare I say, Picasso-like? I think that's the most refreshing aspect of his writing. It speaks to my stretched-over-the-elastic-limit pseudo-intellectual ethos. I can read his books when I'm anywhere from 30% to 80% awake, preferably in a shroud of disillusionment.
I read Player One, Generation A, and JPod (reverse chronological order of when he published them) In all three books, the story would center around a quintet or sextet of characters thrust into an epic adventure against their will. Despite seemingly very different from one another (different walks of life, different parts of the world, different upbringings), they are united first by their bizarre circumstances and gradually come to the realization that they are more alike than they have thought. That they are all equally screwed over, but somehow things work out. More or less.
There's a stronger autobiographical presence in JPod than in Player One or Generation A in that there is one main narrator and more of the characters are connected to him than others. Later in JPod, however, the narrator's work life and home life become unwittingly stirred into a peanut butter and wasabi mix. Perhaps Coupland has felt like that at some point in his life. I can only speculate...
There's also a lot of stream-of-consciousness in JPod which many other readers have found distracting, not to mention random typographical feats like the word "ramen" in size-7 (?) Helvetica repeated for one whole page, or the first ~50,000 digits of pi, or random Chinese characters. I personally loved the "ramen" page. Hit rather close to home.
Perhaps these are meant to be subliminal bombardment of modern culture? Or the author got lazy? In any event, I found this somewhat amusing. The digits of pi though is rather overdone and a waste of ink. ~200 digits would be adequate. :-P
I might give his earlier books a read, although I have gotten a pretty good idea what to expect. He seems to alternate between rambling stream-of-consciousness (JPod) and intricate story weaving (Player One) and somewhere in between (Generation A). I can empathize too, even though the longest (fan)fiction I've ever written is barely 6,000 words. Or was it less than that? Oh well. So I understand that everyone has more inspired days than others. I'm still a fan.