The songs I listen to most obsessively are Morrissey or Smiths songs, a fact which does much to explain my presence here. The songs change depending upon my subconscious need (or whatever). I try not to analyze it.
I've lately developed a new OCD behavior, which is that if one of my particular obsesso songs is inerrupted for any reason, I have to start at the very beginning again.
Other songs:
Lou Reed: Perfect Day
Momus: Platinum
Led Zeppelin: Kashmir
Massive Attack: Karmacoma
Beastie Boys: Sure Shot