More specifically, like the Eagles he’s “Stuff White People Who Qualify For AARP Like.”
I have yet to figure out the JB phenomenon. I don’t like him at all and my fiancee loves him. She when we take road trips and let the MP3 players go, I promise him Spice Girls in exchange for no Jimmy Buffett. (Hey, I don’t think the Spice Girls are musical geniuses or anything… I’m nostalgic when I listen to them. Reminds me of middle school when I didn’t have any problems.)
Not a fan. I do enjoy that lifestyle, but it kind of wrecks a nice beer on a Caribbean beach when the bar has his CDs on constant rotation.
There’s one song where he raps. That was a deal-breaker for me.
I’ve never actually heard a Jimmy Buffet Song, nor have I ever met someone in this part of the world who could be described as a “Parrothead”- which surprises me, because Australia has a rich and vibrant “Beach Culture” and you’d think a guy who sings about getting drunk on the beach would be a National Icon here, even if he was an American. 
Martini, try these for an idea:
In two weeks, I’ll be breakfasting at Margaritaville. I can already taste that omelet!
I think the “Gulf + Western” description sums it up pretty well, actually. Not my cup of Ceylon’s finest, but it’s inoffensive enough and I can see how it appeals to the “working in a Mid-Western/North-East office” demographic. 