Hometown by the Obama Foundation

Barack Obama was, among other firsts, the first POTUS who shared his listening habits with the public through Spotify playlists. And though he hasn’t personally curated any music selections since leaving the White House, his Chicago-based non-profit recently debuted the first iteration of Hometown, a collection of tracks handpicked by Chicagoans that remind them of home.

Comedian Cameron Esposito opens the playlist with one Chicago band covering another, JC Brooks & The Uptown Sound putting an unlikely retro soul spin on Wilco’s fragile epic “I Am Trying To Break Your Heart.” But while songs from and/or about Chi-town dominate, not everyone is so literal with the theme; actor Nick Offerman picks two Tom Waits songs that remind him of his theater days in Chicago (neither of which is Waits’s 2011 track “Chicago”).

Kanye West looms large over the playlist, with three curators picking his tracks. One is West’s young protege Chance The Rapper, who singles out the sweetly nostalgic “Family Business.” A few tracks later, President Obama’s former Deputy Press Secretary, Bill Burton, picks Chance’s own “Blessings,” with a tip of the hat to Chance’s father’s work on Obama’s first campaign. But despite some recurring threads, Hometown offers a pluralistic view of Chicago music, with equal room for Liz Phair and The Staple Singers.