I actually kind of like listening to Dave Matthews--as far as what he's doing, it is fairly simple--playing "modal" style, which is to say, playing a vamp of partial chord positions(in Superman, it is the   two finger E 7 figure, first in Sixth position, then in fourth position, then altered so the index is on the G string third fret and the ring finger on A string fifth fret, then to the regular E chord) against the sustained low note of a single chord--

It gives a moving bass line against a drone--which is a nice full sound that all the acoustic guitar players like because they can get a lot of power and movement at the same time, without need of a band.

The lyrics are of the sort that the young people like today, which are, basically, oblique--they sound like they are about something, but you never know quite what--rough time to be young, I guess--

As to the singing style, well, its the same thing--every generation has it's "Alpha Male" singing style-- --I remember when everybody tried to sound like Frankie Laine--

The thing is that he is considered to be mass-market pop by this generation's musical cognescenti, and, therefore, beneath contempt--right up there with Hootie and the Blowfish, Alanis Morrisette, and possible even Jewel--

So the good news is, you don't have to like him to be hip--to be hip, check out The Killers, or Hot, Hot, Heat, or Modest Mouse--