Wanderinginspace has provided us with some new clues and corrected and connfirmed the answers, so the ones listed on the post are all correct as of right now.
Here are the clues:
6 is hard… southern rocker
7 is also tough… part of a group that justifiably probably should have 2 people in here.
15 is tough. what he is holding is a cup of tea.
22 don’t think its a tough one… based in part on a pretty well know image of him on a live album.
23 also not hard i think. other than dylan… who is the biggest male folk rocker?
25 i think is the hardest one. very well respected/influential by other musicians, but probably not recognizable by a majority of the public. same goes for #7.
27 he has been mentioned in here, but not for the correct number.
28 is Stevie Nicks which was ruled out accidentally as i had been mistakenly saying 65-75. its really more about a generation/attitude of rock despite what years they peaked.
Thanks all of you for participating!!!