When Tom Allen started work on his first book, he must have been about 35, which is the same age Dante was when he began writing The Divine Comedy. Like Dante, Allen is concerned about God and love and what happens after death. Like Dante, he wonders about the architecture of heaven and hell. But unlike Dante, Allen writes comedy in the modern sense, and Toe Rubber Blues is aiming to put a smile on your face and some warmth in your hardened old heart.

This collection of 28 essays succeeds more or less. For example, Allen meanders from consideration of direct deposit of paycheques to Casual Fridays to undershirts to a belief that “bankers are supposed to be boring…Sure, they can seem greedy and inhuman, but at least you know where you stand, even if it’s over the trapdoor.” Or from the abstract concept of happiness to binary choices to a riff about politics. For example, politicians “throw their hats into the ring and knock at your door, hat in hand. But at the drop of a hat it becomes clear they were just talking through their hats.”

Along the way, Allen summons up some marvellous images: daydreaming at 15 while lying on his back in the sanctuary of the church he was supposed to be painting, and, at 25, trying to figure out where on his person to stash several dollars in quarters while nude at Vancouver’s Wreck Beach.

Trained as a bass trombonist, Allen currently is host for the classical music morning show on CBC’s Radio Two. Before that, he was the voice of Fresh Air, broadcast weekend mornings in Ontario and Quebec. Several of these essays appear to date from then, which may account for Allen’s concern with aging: the show’s high point for many years was its “Over Ninety Birthday Club.”

But, while Allen laments the fact that he is balding, he is not old by today’s standards, and so his insistence on his mortality seems forced. The 1990s are considerably different from the 1300s, which is when Dante wrote. Just ask that other Canadian writer born the same year as Allen: Douglas Coupland, the author of Generation X.