Perhaps you caught his recent press conference, when he was asked about this. Looking surprised by the question, President Bush responded, "That's interesting. I hadn't heard that." It was a reminder to Americans that a guy who doesn't pump or pay for his own gas isn't truly in touch with regular folks.
And it's something you hear with regularity from personalities who have hit the big time financially. It's not uncommon to hear them talk about a lavish vacation, a Vegas weekend, a luxury car purchase, the free tickets to the suite they received, or the limo ride to the concert. Part of this may be expected by listeners who totally understand that they're listening to stars who have cashed in on their success. Some live vicariously through these DJ stars and their rock star lives. And clearly, a portion of the audience can afford these types of extravagances - or buys them anyway. Howard Stern has typically talked about his riches and perks, and he's often made it entertaining. Although I would submit that he was always more relatable playing "everyman" with regular guy problems with Allison and the girls, than when he dated strippers in limos.
It's the same thing with the local morning guy, and even the syndicated show that speaks to millions of listeners around the country. More often than not, they are better off being relatable, and in-touch with their audiences, rather than above them. In these recessionary times (yes, it is a recession), keeping it real is the way to go. We're going through a difficult period in this country, where foreclosures are common, jobs are tenuous, and it's tough for the "Average Joe" to afford concert or baseball tickets. Personalities that maintain great eye contact throughout this tough patch will most certainly have an edge - not just with their listeners but with many others who work at the station who are struggling to make ends meet.