OK, this is for standard issue bar bands, not tributes or niche bands. Most of us play hits, or songs that are charting now that might not stand the test of time.
But every now and then you just have to whip out one self-indulgent, random, B-side, relatively-unknown, never-saw-it-coming song and rip it because the band wants to do it.
Sometimes they wind up catching on locally and become a favorite. Such was the case in the late 80s and early 90s when a regionally-popular band I played in (I was a kid and the rest of the band members were in their thirties) played Cowboy Song by Thin Lizzy. (The intro is kind of a downer. Listen at least a minute or so. Skip to 45s if you have no patients.... like me.)
Thin Lizzy Cowboy Song - YouTube
It became one of our most requested songs. I'm not saying the song is "obscure", per say. But your average bar goer, even back then, had no idea who did the song if they had even heard it. So that one worked out well.
Really, Cowboy Song by Thin LIzzy "obscure"? Man, I was there. This tune was on constant airplay repeat in '76. Takes me right back to the skatepark where this was pretty much one of about 8 tunes constantly wailing over the PA.
I guess they didn't license their back catalog to the oldies conglomerates, so they don't get heard all the time.
: