Two of the screencaps are TOTAL MYSTERIES. Nobody has guessed either artist or song correctly for either #4 or #8 yet. Every other cap has had at least one correct guess. The thing about #8 (I smell a hint coming on!) is that the women pictured in the shot have nothing to do with the artist (so far all the guesses have been for girl bands.) The artist is a guy. One guy. One kinda weird guy, but back then, who wasn't?
Now that I've said that, it's only fair to let those who've already made guesses do a second one for #8, so if you feel like thinking it over some more, feel free to reply to your original comment with an updated #8.
#4, well, you're on your own with this one, but again, the person in the picture has nothing to do with the actual artist himself, herself, or themselves. Whee!
And to help soothe your soul in its hour of need, here's a picture of my future wife:
She was picking out a contest winner! MAYBE IT WAS YOU!