1. HD580 (Oehlbach) - in terms of sonic quality, the clear winner of my cans. Bests the 595 with a velvet-smooth midbass through midrange to lower treble (without grain), extended highs, better detail, bass impact, and a more refined presentation. (From my description it does seem like a big difference compared to the 595, but realistically, the 595 is nearly as good). When using the stock cable however, the 580 is not as good as the 595.
2. HD595 - in terms of enjoyment, this would be #1. It has a certain quality to it that makes music more fun to listen to. It is very involving (envelops you in sound), comfortable, and something that can be listened to for hours without fatigue. My only (extremely minor) complaints include a little grain in the mids and lower treble and despite the fact that there's plenty of bass and it extends nicely, there isn't enough bass impact - for instance a bass drum sounds too "polite."
3. HD25-1 (Stock HD580 Cable) - when isolation is important
4. KSC-75 - I don't miss my Grado's thanks to these (ok... they're no Grado headphone but they come reasonably close and are just as fun and I can't help but smile when I think about what I paid for them)
5. PX200 - I'm one of the lucky ones who can get a great seal - LOADS of bass. Mids are honky and the highs roll off pretty dramatically, but for really portable closed phones that offer some minor isolation, I can accept the shortcomings. The honkiness and the highs can be fixed with EQ. I smile too when I remember that I only paid $29 for them.
6. MX400 - Just a great ultra-portable solution. They sound pretty good flat, but a little EQ can add some nice bass presence and make them sound like full-sized cans. I don't need to say anything about the price