How Many Times Do You Have To Listen To Understand A Piece Of Music?

When I first heard Captain Beefheart, it sounded like Frank Zappa and the Mothers on acid. I figured that out in five minutes. 

Some of my favorite artists I love the music right away, but can take at least 5 or 6 listenings before I can even figure out what the song is doing.... 

To quote Beefheart, "When It Blows - It Stacks."

That is all ye know, and all ye need to know.

It varies by song obviously some are more accessible than others. Countless times I've decided a song was the best on an album only to later consider a different song I didn't care for originally best on an album.

Classical music and good jazz—if it’s music that grabs me: hundreds and hundreds of times. In my case, Ralph Vaughan Williams, Charles Ives, Charles Lloyd and Charlie Mingus. If I listened to these in vinyl I would have worn them out by now. In fact I did wear out Three or Four Shades of Blue back in my turntable days.