So far I have read of his:
Generation X
Microserfs
Miss Wyoming
Girlfriend in a Coma
I am up for reading more because I like his writing style. One attitude I got from the 3 books I read was an underlying theme in all the main characters: in order to find happiness, one needs to make one's own way, which almost always means breaking out of the world's standardized categories. If his other books don't project this, I would be surprised.
In Generation X, the characters, after already dropping out of the corporate hullabulloo, drop even further out at the end of the book, buying into a hotel in the desert. In Microserfs, all the former employees of Microsoft leave their jobs and join a startup created by one on their ranks. And in Miss Wyoming, the two characters slated to fall in love have taken this extreme of dropping out from extraordinary occurances that happen to them that they take advantage of. In each of these books, you are left knowing that the story goes on and it's not up to you or the book to tell the whole story.
In addition, all of these characters were in a rut previously for many years, indicating a long history of lives that, while being stagnant, are full of reflections and memories. It is a challenge to accomplish this as a writer, to not make the past the focus but also enable it to be the motivation for current thought patterns, for we are so built on what we have already experienced.
I can't help but wonder if/how Coupland himself may have dropped out of the system when it was clear he would never be happy with his outcome, as it seems to be such a strong presence in his books. Because of this, among other things contributing to his popularity, I can see why Coupland has become such a cult figure, whether that's what he wanted to happen or not.
In these three books, there is not much indication that the characters suffered more than any average, struggling middle class cog suffers. Extreme poverty is not represented, but there is a smug attitdue toward exhorbitant wealth, judging it from its source and execution. The sarcasm displayed in these stories is not snooty nor immature, but regulated and educated, though not overt, meaning that the accumulation of knowledge is not over our heads but gathered in the ways common knowledge is gathered today (from newsblips and magazine blurbs). Because of this, Coupland's characters, both the protagonists and those set up merely for contrast, are people we are, relate to, or have seen in everyday life.
While they could be referred to as the modern everyman, Coupland's characters are given depth, quirks, good natures and quick wits. While the people may seem common, Coupland's description of scenes (as well as natural environments, which seem to be where characters search for in the midst of modernity) is supurb and yet flows in the language I think is most widely accepted: brief, but encompassing a lot of detail to convey a whole picture.
Another element of Coupland's style is community, a coming together of individuals who, while not at ease with it, have accepted that if they never get married, they have each other. These stories focus on people and friends the way they do tend to end up: tangled up in one another, spanning generations and locations, providing certain needs in certain crevices of our lives, and yet never disappearing from view, even after their deaths. The accounts speak from a generation that has recognized the distance from their families (usually the protagnist's parents are still married but have settled into a state of suspended animation while the other characters are children of divorces), and while striving to maintain connection and respect for their elders, also strive to articulate what that distance has done to them in adult life.
Not everyone will relate, but I think most people from a wide age group will be able to appreciate Coupland's efforts. Wanting to think myself a writer, however, I am more curious as to what Coupland himself was like, if he acted in these capacities, or like me, did he merely admire these characters and wanted to be more like them.