There is no conversation about music that is less interesting than one party talking about a band/album/song/genre that the other has never heard of or heard. Obscurity is a necessary evil when dealing with music, particularly for those constantly seeking a new aural thrill. But taking pride in obscurity is one of the lowest forms of music appreciation, second only to disliking an artist based solely on popularity.
I teach guitar lessons as a day job -- or, more accurately, late afternoon/early evening job. I am frequently put into situations where somebody who comes from a completely different place in life (such as "loves Avenged Sevenfold" or "grew up on AC/DC" or "is eight years old") asks me what music I listen to. I rarely answer this with complete honesty, and I usually fall back on an answer representative of something larger -- Radiohead, The Beatles, jazz.
I respond that way because I hate the way a one-sided music conversation feels. I become anxious when a discussion or small-talk devolves into "have you heard (insert band here)?" That game was a blast when I was younger, but hoarding music becomes less fun with each passing year.
The overarching issue is the difference between our public human interactions and our private explorations. I find that I listen to music much differently when I am alone, and this affects what I actually listen to when I am with another person. Whenever I put on a song that I privately enjoy for somebody else, I become nervous. It is an intimate experience, revealing something personal about myself. Maybe this is why I have such a hard time relating to the bragging mentality of so many obscurity fetishists; it comes off like divulging unsolicited information about his sexual conquests.
Also, the immature quest to find music that nobody else has heard closes off the potential for common ground with another person when discussing music. I find it much more satisfying to talk to somebody I have never met before about Kanye West than to tell them they should listen to (insert band here).
But when an interaction about something obscure can be deep and thoughtful between two people, it is strangely powerful. A friend who I rarely see casually recommended a Fela Kuti record to me a few months ago, and I loved it. I was inspired to recommend to him a Brazilian artist I had been listening to for weeks, but hadn't mentioned the name to a soul. I remember waiting to hear back from him as though I was anticipating a response to a "do you like me? check yes or no" note. He emailed me to say he likes it, and even though we haven't talked much since, I feel inexplicably closer to him.
My dislike of obscure music conversation might seem hypocritical. After all, I write about music for the RFT and, therefore, am in the business of recommending artists to others. But we have a system worked out here - we being everybody who participates in music dialogue via online or print publications, not we the Riverfront Times and the greater Village Voice Media conglomerate. The information is optional, and readership is consensual.
Furthermore, if the subject of a piece in the RFT happens to be unpopular, part of the motivation is to remedy that injustice, to suggest what is worth checking out so the reader/listener is fulfilled and the artist is rewarded for their good deeds. The standard profile of the pretentious music fan involves a selfish desire for the artist to not succeed - not wanting to "share" the music with others, not wanting to pay extra money if the artist begins playing larger venues, et cetera.
Obscurity is not poverty; it is not something we can campaign or work to eliminate. But it is something we can destigmatize with tasteful conversation and a selfless attitude.