Almost one-third of Pitchfork's 2019 roster is from in or around Chicago. Credit: Illustration by John Garrison

The best mixtapes are eclectic, showcasing a broad range of styles and artists and thus encouraging listeners to explore unfamiliar catalogs. This year Pitchfork booked so many acts from in and around Chicago that one song from each would fill a side of a 90-minute cassette, so I made a streamable mix for the occasion. All 12 artists have released music in the past year, and it’s almost all available on Spotify—the lone exception, the AACM Great Black Music Ensemble‘s Live at the Currency Exchange, Volume 1, can be purchased at their performances.

1. Ric Wilson, “Dan Ryan Traffic”

In a little more than a minute, Ric Wilson delivers a heartfelt ode to those who’ve fallen victim to alcoholism or gun violence or been marginalized by Chicago’s segregationist practices. It’s bittersweet but ultimately hopeful.

Sat 7/20, 1:45-2:25 PM, Red Stage

2. Lala Lala, “I Get Cut”

Postpunk band Lala Lala gleefully twist anthemic indie rock into off-balance shapes, pelting it with quick rhythmic bursts to keep everybody on their toes. On the verses Lillie West sings with dry restraint about surviving trauma with the help of love, and on the chorus she hollers with enough force to suggest she can overcome anything.

Sat 7/20, 1-1:40 PM, Green Stage

3. Freddie Gibbs, “Cataracts”

Freddie Gibbs artfully mixes joy and sorrow in a track about chasing the sort of vices that can upend lives, and as usual he delivers his insights at a blistering pace with plenty of swing. For the instrumental, producer Madlib sampled “Teach Me How” by Ohio soul band Wee, which appears on their 1977 album You Can Fly on My Aeroplane, reissued in 2008 by the Numero Group.

Sat 7/20, 6:30-7:15 PM, Blue Stage

4. Whitney, “Giving Up”

The first single from the country-soul band’s forthcoming second album, Forever Turned Around, has everything you could hope for from a Whitney song: it delicately balances the somber and sweet as it climbs to a celebratory finish.

Sun 7/21, 6:15-7:15 PM, Green Stage

5. Tasha, “Kind of Love”

Singer-songwriter Tasha crafts indie-rock lullabies so calming they could help coffee get to sleep. On “Kind of Love” she maintains her tranquility even as she evokes the queasy excitement of a romance that can turn your stomach inside out.

Sun 7/21, 2:45-3:30 PM, Blue Stage

6. Valee, “Yoppie”

Stylistically adventurous rapper Valee radiates bliss even as he mirrors the slack energy of this track’s dreamlike instrumental.

Fri 7/19, 3:20-4:10 PM, Red Stage

7. Mavis Staples, “One More Change”

Pop music would be so different without Mavis Staples, and she’s still flexing her creative muscles. When she leans into the earthiness of her voice on the chorus of the relaxed blues number “One More Change,” she supercharges it with that special Staples gravitas.

Fri 7/19, 7:25-8:25 PM, Red Stage

8. Dreezy featuring Jeremih, “Ecstasy”

Rapper-singer Dreezy recruited Chicago crooner Jeremih for her 2016 breakthrough single, “Body,” and they rekindle its irresistible sensuality with “Ecstasy,” off January’s Big Dreez.

Dreezy: Sun 7/21, 1-1:40 PM, Green Stage

Jeremih: Sat 7/20, 7:45-8:30 PM, Blue Stage

9. Grapetooth, “Trouble”

Indie-pop misfits Grapetooth marry dazed synths and a campfire acoustic-guitar melody for a song that evokes a euphoric late-summer night.

Fri 7/19, 4-4:45 PM, Blue Stage

10. Bitchin Bajas, “Planète T”

Experimental trio Bitchin Bajas first released this ambient track on 2015’s Transporteur via French label Hands in the Dark, but Drag City reissued it last fall as part of a seven-CD retrospective. “Planète T” is gentle and absorbing, so that time feels inconsequential.

Sat 7/20, 2:45-3:30 PM, Blue Stage  v