Rather than resent our longtime contributor Mark Ellwood for his continent-hopping lifestyle, we choose to embrace it. (Okay, fine—resent and embrace.) Welcome to an occasional, and opinionated, series of dispatches from the frontlines of luxury journalism, both at home and abroad.

I hate driving in Italy. And it's not just because of my suicidal fellow motorists, who'll sit in the center of every road until another vehicle—say, the one you're driving—barrels down on them before swerving to one side. Oh, no, what makes driving agonizing in Italy is the radio.

The back catalog here is like a Men's Wearhouse suit stashed in the rear of Italy's Prada-crammed cultural closet. (This is the country that gave us Black Box, after all.) The radio plays an endless stream of what sound like novelty records, and the dial is permanently stuck on 1985 FM. Its only impressive touch are the phone-ins. One shock jock last week, in between spinning pappy pop and Toto, asked his teenybopping listeners this prize-winning question: "Which artist invented perspective?" Try asking that on Z100.

There are plenty of homegrown music stars, too, like Jovanotti (pictured), who's guest-editing this month's Italian GQ. The singer broke through almost 20 years ago as a joke rapper—think of him as the love child of Eminem and "Weird Al" Yankovic—then went into the Italian army for his national service at fame's peak. He emerged an impish, bearded style icon—think Johnny Knoxville by way of Jude Law—and buddied up with Bono for the campaign to end third world debt. His music's no better, though.

But my problems on this trip were more than just the radio.