The painting Northside Southside (pictured above) anchors the series with a romantic projection of Toebbe’s condominium community, East View Park, a cluster of 1920s brownstones just a stone’s throw from Lake Michigan. The artist’s studio, situated in a garden-apartment studio, looms over the picturesque lakefront park near their home, Promontory Point, marking a thematic divide: Northside, slate gray-green and churned up by the wind, and Southside, blue, undulating, and calm. Northside and Southside wryly symbolize both Toebbe’s state of mind and the deep-lying geographical, cultural, and racial divisions of Chicago’s neighborhoods.

The historical and cultural undercurrents that define Hyde Park play through Toebbe’s paintings in patterns and subtle details. Obama’s House offers a simple street view of the former president’s long-empty but closely-guarded residence on the border of Hyde Park’s upscale enclave, Kenwood; seen from the dividing street, Hyde Park Boulevard, the famous home is intentionally hidden by a clump of overgrown evergreens, a symbol of pride and a bittersweet reminder of his presidency. Toebbe’s work explores details that hide as much as they reveal – the old men in the corner of the cafe, the feral critters inhabiting the backyard alley, the crowded reading rug of a kindergarten classroom.