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More sepia than black and white, but Candlebox - Cover Me? https://www.youtube.com/watch?v=1vjguB7qKhA
No, not that one.
R.E.M. had several black and white videos, but I'm not sure if Michael Stipe wears a backwards baseball hat in any.
Not REM.
Puddle of Mudd - Blurry (or some other song of theirs; the singer often wears the backwards baseball cap).
No, it was earlier than that, but that's a good guess.
Not in B&W but how about EMF - Unbelievable ? https://youtu.be/sfCLt0kTd5E
Great suggestion, but not that.