The most engaging passages in Prisoner Of X, Allan MacDonell's appropriately trashy account of his two decades toiling for noted gutter pornographer/First-Amendment activist Larry Flynt, ponder quandaries the average New Yorker editor will probably never have to face. How do you respond when enterprising country businessmen (i.e. hillbillies) try to sell you a videotape of Chuck Berry eating feces? For that matter, what's the appropriate course of action when approached by a man with a video (purportedly) showing Ted Turner and Jane Fonda engaged in a kinky threesome prominently involving a strap-on dildo? Prisoner Of X's most compelling segments function as perverted choose-your-own adventures implicitly asking readers how they'd respond to a series of surreal and ridiculous situations.

MacDonell wound up in many such ridiculous circumstances over the course of his two decades working for Flynt, from covering grubby porn shoots to digging up dirt on Republican lawmakers. In the hands of a better, less bitter writer, his experiences might be engaging. Alas, the problem with any memoir from a Hustler writer is that it's bound to feel like it was written by, well, a dude who wrote for Hustler. For a Hustler scribe, MacDonell undoubtedly qualifies as the second coming of Don DeLillo, but by loftier standards, his prose is overwritten and under-funny, constantly straining for laughs that never arrive. MacDonell came to Hustler as a punk-rock fuck-up, college dropout, and low-rent-'zine scribbler with a weakness for drink and a wide array of illegal drugs. Then he cleaned up and rocketed up the Hustler corporate ladder, eventually becoming Flynt's right-hand man.

Once MacDonell makes the jump from underachieving druggie to sober company man, the vaguely desperate self-deprecation permeating the book's first half is replaced by the bulletproof self-righteousness of the reformed doper. There's nothing righteous about MacDonell's abundant anger, nothing edifying about the withering contempt he heaps on subordinates and co-workers. He doesn't seem to realize that nastiness devoid of humor or insight is just ugly.