Sherr is right on the money, of course. While one can probably shoehorn almost any band or musician into some category of "lifestyle rock" (where the lifestyle catered to may be bookish/intellectual, sophisticated/aware, ironical/kitschy, angry/rebellious, etc.), there is something profoundly insidious about Buffett's music in particular. A novelty act that somehow transcended severe musical limitations and built an empire on what is essentially a Slurpee with tequila, Buffett's music is irredeemable in that it trades on the supreme smugness and self-satisfaction of middle-aged doctors and lawyers (and their progeny, who even as teenagers dream of one day being middle-aged doctors and lawyers themselves). The central message of Buffett's entire catalog is basically, "Let's all sing about how sweet and easy life can be here in the highest tax bracket." No matter how you slice it, that's a pretty lame oeuvre.
Songs like "Margaritaville" and "Cheeseburger in Paradise" also have certain unavoidable associations. Button-down oxford shirts tucked into slightly too-short khaki shorts, worn with loafers sans socks. Sunglasses attached with Croakies. The schools of the SEC. Practicing air-golf swings (i.e., pretending to swing a golf club, even though there is none in hand) during conversation. Gated communities. Those incredibly retarded black "W The President" car stickers. Date rape. And a bunch of other stuff that's pretty hard to overlook.