Does it have to sound good for you to like it?

Charlie Parker can be rough to listen to on many poorly recorded outings. But he is so phenomenal you can't avoid appreciating and enjoying his playing even on the worst recorded records. 

My latest favorite rockers, Band-Maid (from Japan) have several mediocre recordings on CD of otherwise great material. Their excellent youtube videos make up for this however, so it's not a total loss. If you haven't listened to them already  pull up their songs "Hate?" and  "Play"  on youtube. You won't be disappointed. After a month of stumbling across Band-Maid, I'm starting to think they're the best rock band to come around since the Stones. High praise indeed. Don't miss out.

Mike

Yes and no. For example, the recordings of Robert Johnson or Feruccio Busoni are not easy to listen to.  But for seminal recordings like those, or bootlegs of of extraordinary performances (e.g., Hendrix, SRV, Parker) or rare, or even unique recordings, sometimes there’s no other choice.  

then there’s the problem of live performances vs studio.    

Like almost everything, it depends. If it's background or on the go music, then I'm not so critical. If it's a set down and listen, then yes it has to sound very good, or I feel I'm basically wasting my time. 

With literally millions of songs to access, I would find it mind boggling why I would listen to poorly recorded music. If your tastes are limited, I could see it. Not an issue for me.