re: Attempting to get into Classic Rock - Where do I start?

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I'm pretty diverse there. It's probably easier to list what I don't like. I like folk stuff, jazz, some young people R&B stuff like Khalid, old school country (not 90's country though), I enjoy some softer rock like some Fleetwood Mac songs or "Fast Car" by Tracy Chapman.

All of that to say I'm open to just about any sound/style, although I've never particularly liked screamo/metal stuff. I like to hear and understand most of the lyrics.

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With this description, check out Grateful Dead. Seriously. They have a lot of stuff with jazz influences and also a lot that is very earthy and folksy. They have some cowboy songs and you can find some live versions of them playing Mama Tried. Listen to American Beauty and see if any of it catches you. From there, you have to go exploring live shows. I can give you a list that'll keep you busy for a long time.