How do music venues reconcile competing desires for popularity and uniqueness in their bookings? According to 25 semi-structured, in-depth interviews with the staff of licensed and unlicensed music venues, gatekeepers tended to prefer ‘weird’ music in terms of unconventionality and even obscurity rather than focusing on cultural similarity through genre conventions. Respondents described at least three ways to reconcile this internal tension of cultural-economic value. A few licensed venue administrators took popularity within the ‘underground’ as an index of value. Others constructed a narrative of building bands from obscurity to success in terms of both economic and cultural value. However, most respondents described strategies of differentiation between cultural and economic value in their economic relationships. This final way of understanding the cultural economy extends Zelizer’s theory of relational economics to find that economic actors do not only differentiate transactions according to social ties but also may differentiate their exchange relationships according to opposing value judgments.