Bob Dylan's Hifi?

As A guess I would say he uses a pair of AR-3s with some old tube amp. Maybe a HH Scott integrated. Probably some massmarket CD player, and an old Empire TT.
Total wild fantasy... but IMO what he has.

Striies me as a guy who doesnt really think about it much, he hears or experiences music on a different level not worried about expensive gear.

I agree with Chadnliz. When a musician listens to music they are more concerned with phrasing, time signature, texture, message, emotional rhythm and progression, feeling. Are they moved/inspired etc. I am sure we would be surprised with simplicity of their set-ups. I envision a vintage set-up ala Sansui, Pioneer and Advents or Cerwin Vega, connected with zip wire. Like many of us they listen to the music not their equipment.

I am equally sure their are some poseurs out their who have to put on a show for people who may stop by or do an interview. They are generally the artists who are driven by other things than being a "true musician".