I only ever get obsessed with a genre when I'm first introduced to it and there's a strong connection. Then I like to look for music that exemplifies exactly what I like about the genre. If an artist has enough songs that make the cut, I'll listen to them a lot and see if they have staying power. Otherwise, I make sure they have enough in common with other songs I already have so that they can be listenable "filler" songs. I don't like wasting any of my time with disposable music (mostly because I purchase most of it).
Really, I don't like being obsessed with artists because I find it makes me want to like some stuff they put out that I otherwise wouldn't care for. I tend to prefer approaching music on a song-by-song basis instead, and focusing on two or three genre obsessions at a time.
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