I guess maybe "well established" to me means they are known in more than just a certain region. For example, Vanity Crash are beloved in Cleveland/Akron(and some Columbus/Cincy/Pittsburgh/Detroit/Indianapolis/Louisville/Buffalo) bars and even open when major bands come to town but I don't expect anyone to know them here in NYC unless I've introduced them myself. Also, to be fair, you did accidentally type "Crave Wives" the first time which definitely didn't ring a bell whereas "Crane" vaguely could if only due to "The Decemberists" album title.
To answer about Conan: often those folks are getting their first national exposure so I'd probably say they could be considered "upcoming artists" or even perhaps "breaking" but when that's the case, they certainly haven't already established themselves yet at that point.
Marti, that makes far more sense now. I'll check out his lyrics and hope someone who actually does sing covered him to see if I like the songs themselves.
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