Conversations about Madison and Milwaukee often focus on how different the cities are, or how strangely disconnected they are despite being only 70 miles apart. Tone Madison‘s Scott Gordon recently got a chance to trade notes with two journalists in Milwaukee about the challenges and opportunities that Wisconsin’s two biggest cities have in common.

Matt Wild and Tyler Maas are the founders and editors of Milwaukee Record, a website covering music, culture, and all sorts strange civic issues in Milwaukee, like the quest for a new Milwaukee flag. Our websites also occasionally collaborate and share stories. I was in Milwaukee recently and we sat down at the Milwaukee Record’s offices in the Bayview neighborhood to talk about how both cities are seen as being at odds with the rest of the state. We also traded notes on some developments both Madison and Milwaukee are dealing with in their arts and culture scenes, including the rise of a ton of promising Wisconsin hip-hop artists, and the struggle to build more supportive communities for musicians and artists.