I don't have one, but feel I could throw my opinion around.
IMO, since, in most occasions, I'm very function over fashion, I consider the classic to rock.
I personally have about 80 gigs of music, and a little over 100 movies, not to mention various complete seasons of anime.
For only $50 more than a Nano, the classic is a very great grab.
Also, don't mind the pricetags, Apples pricing doesn't make sense. Example? Ipod Touch (16gb) for more than a Classic 160 gb.