Compared to its mega-fest brethren, Pitchfork Music Festival has always been one of the most manageable, exciting, and comprehensive showcases of Chicago’s thriving and eclectic music scene. This year is no exception, with 11 local acts (including Freddie Gibbs, from Gary) on the lineup, ranging from gospel and soul masters to jazz mainstays, rising indie-rock outfits, and upstart rappers. Read on for an act-by-act guide to the city’s exceptional talent performing this weekend.
Friday, July 19
Great Black Music Ensemble: 1 p.m. (Green Stage)
Pitchfork Festival founding director and booker Mike Reed is an established figure in the local jazz scene, which typically means that the genre appears on the lineup in some form. This year is no different, with a group featuring members of local nonprofit the Association for the Advancement of Creative Musicians (AACM). These are all versatile, incredibly skilled, intergenerational musicians from a variety of different backgrounds, so expect several different movements and styles of jazz played with a gleefully improvisational approach.
Valee: 3:20 p.m. (Red Stage). Thursday show at Thalia Hall
This local power player has a full-length debut tentatively scheduled to drop in the fall, fresh on the heels of Runnin’ Rich, the red-dog-covered EP he released this past June. Check out his deceptively understated style, filled with clever wordplay and backed by beats harder than concrete.
Grapetooth: 4 p.m. (Blue Stage). Friday aftershow at Metro
The collaboration between producer Chris Bailoni and Twin Peaks’ Clay Frankel make synth-powered rock songs so anthemic that their live shows can get overwhelmingly joyful and rowdy. The duo are known for inviting the crowd up onstage for its hit “Trouble”; while that’s unlikely to happen at a big music festival, expect similarly party-leaning theatrics.
Mavis Staples: 7:25 p.m. (Red)
This soul, gospel, and blues powerhouse just celebrated her 80th birthday last week and still manages to do things singers half her age can’t, like play energetic shows in 90-plus-degree weather. Anticipate a career-spanning set skewed more favorably toward her latest LP, We Get By (fingers crossed that Jeff Tweedy, her longtime collaborator, and his son Spencer join her onstage for a couple songs).
Saturday, July 20
Lala Lala: 1 p.m. (Green). Friday aftershow at Metro
Fronted by the U.K.-raised Lillie West, this indie-rock outfit first gained notice with last year’s excellent The Lamb. Your favorite local band’s favorite local band has toured with acts as big as Death Cab For Cutie and WHY?, and recently added local mainstays Nnamdi Ogbonnaya, Sen Morimoto, and V.V. Lightbody to its touring roster.
Ric Wilson: 1:45 p.m. (Red). Friday aftershow at Schubas
This rapper and prison abolitionist introduces many threads of musical history into his buoyant hip-hop, leaning on soul, disco, funk, and electronic music to diversify his songs. Though a full-length is on the way this year, the real highlight comes with his mid-show “soul train” lines, where he separates the crowd down the middle and turns the gap into a respectful dance party.
Freddie Gibbs: 6:30 p.m. (Blue)
The last time the Gary, Indiana, native played Pitchfork, in 2015, he was backed by the esteemed and dynamic producer Madlib, fresh off their collaborative album-of-the-year contender Piñata. While Madlib isn’t scheduled to join the rapper onstage for his 2019 appearance, the two have just released Bandana, a full-length every bit as good as its precursor. Gibbs will likely play some cuts from the new release, but even if he doesn’t, his hard-nosed, gritty showmanship is the perfect Saturday-evening appointment.
Jeremih: 7:45 p.m. (Blue)
The hottest local R&B singer first played Pitchfork in 2016, when Chance the Rapper memorably and briefly joined him onstage. Now the Chicago soul singer is back for a later slot at the festival’s intimate Blue Stage. Since his festival debut, he’s released a collaborative EP with Chano as well as MihTy, a full-length with pop and hip-hop polymath Ty Dolla $ign.
Sunday, July 21
Dreezy: 1 p.m. (Green)
After years of press hype from her early mixtapes and her breakout Jeremih-assisted single “Body” from 2016, this South Side rapper returned in January with her sophomore studio album Big Dreez, a full-length that features marquee guests like Offset, Jacquees, and, of course, Jeremih again.
Tasha: 2:45 p.m. (Blue)
The Rogers Park-raised singer makes delicate songs that blend folk and indie rock. Intimacy isn’t a great fit for crowded festival environments, but Tasha’s strong voice and stellar songwriting have the necessary power to overcome any distractions in the Union Park grounds.
Whitney: 6:15 p.m. (Green)
Whitney’s first album, Light Upon the Lake, was the soundtrack of the Chicago summer of 2016, and now the band is set to debut a handful of new songs from its follow-up, Forever Turned Around. A counterpoint to the ramshackle and sunny sounds of Whitney’s debut, the sophomore LP boasts sweeping strings and a heaping dose of wide-screen melancholy.
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