I rediscovered Internet Archive as a source of some glorious music, so my picks for May are all from there.
Live recordings and old blues recordings can get a little tinny at times, so I've mostly listened to these recordings via my KEF Q300 loudspeakers or my Fostex T50RP MK3 headphones. You can read more about my speakers in an earlier entry, but these over ear semi-open headphones are something I've been wanting to mention.
The Fostex T50RP MK3's aren't the run of the mill over ear cans; these are planar magnetic headphones which means they aren't normal everyday speakers like you are used to seeing. At ~$160, they are a bargain if you compare them to my Sennheiser HD600's (although I have no reason to rid myself of those gems). I added HM5 angled velour pads for comfort and absolutely adore the fullness of sound they provide.
There is something I can't explain in the bass of these headphones that make them unique. The crispness of the bass eases some of the sibilance that makes listening to a few of the recordings below fatiguing while enjoying in one's own company.
Andrew Bird Live at Paradiso 2005-05-01
Kevin Drew Live at 9.30 Club, Washington, DC 2007-11-18
Elliot Smith Live at Roseland Theatre 2000-11-10