Early Friday afternoon time slots at Pitchfork are often filled with up-and-coming hometown acts, and this year the honors go to indie-rock trio Dehd. A set composed largely of songs from the Chicago band’s most recent album, 2020’s Flower Of Devotion, would be the perfect way to ease into the festival. Dehd is full of heartache and longing, and we imagine lead singer Emily Kempf’s lush vocals and Jason Balla’s reverbed guitar will do well in the open air, drifting out echoey and dreamy across the park. [Laura Adamczyk]

When London experimental rock band black midi played SXSW in 2019, X’s marked the band members’ hands, as they were still too young to drink in American bars. As young men who did not have PR or a social media presence, the members of black midi instead relied on word of mouth for hype around their shows. What unfolded during this daytime show was a captivating set that kept the audience on their toes—as kicked off by a loud, garbled intro to Kacey Musgraves’ “High Horse.” The frenzy of lead singer Geordie Greep, underlined by the cleanliness of the instrumentals, is not something to miss; it will be interesting to see how the young lads have evolved two years and two albums later. [Gabrielle Sanchez]

It’s been over a decade since the Fiery Furnaces have released new music and gone out on tour, and it’ll be exciting to hear what the oddball storytelling siblings from Oak Park have been up to. The Friedbergers’ first single since 2011, last year’s “Down At The So And So On Somewhere,” is of a piece with the band’s previous work: It’s peripatetic, it’s a little mournful, and it’s got those mildly proggy synths in there. And while we think it would be quite the move for Matt and Eleanor to play their epic rock opera Blueberry Boat front to back, theirs should be an interesting set no matter what they play. [Laura Adamczyk]

Big Thief’s recorded output is the kind of material that makes you want to turn up your headphones and focus, as the beauty of the band’s austere indie Americana is often quietly intense. Thus, a live setting is the perfect chance to finally hear some of those lovely words Adrienne Lenker’s been singing with more clarity, as well as get a chance to experience an act that’s been justly lauded for the transportive intimacy of its performances. [Alex McLevy]

As her star has risen over the last year, Pitchfork bumped Phoebe Bridgers up to well-deserved headliner status. While her music is far from high-energy, jump-around festival sounds, Bridgers’ delicate voice should wash over the crowd to provide some moments of much-needed public emotional catharsis. One of the captivating things about Phoebe Bridgers as a bonafide “sad girl musician” is that you never know what to expect: We can only hope she smashes another guitar on the ground during “I Know The End.” [Gabrielle Sanchez]

It’s still hard to explain Bartees Strange to those who haven’t heard his engaging musical mashup—a heady amalgam of folk, country, house music, rap, and more—without eventually resorting to a “just trust me, it’s good.” But the chance to hear him display those genre-blending chops on a massive outdoor stage is an exciting thought, with the musician jumping from one song to the next, a sort of sentient live jukebox who never wears out his welcome. [Alex McLevy]

As we said back in 2018, when Jamila Woods’ final performance of Heavn was named one of the best live concerts of the year, “music festivals help make Chicago bearable, but artists like Jamila Woods are what make the city great.” And we’re always excited to see the kaleidoscopic genre-hopper (and Pushcart Prize-winning poet) take to the stage, given her knack for blending spectacle, social issues, and soulful music in ways few others even attempt, let alone pull off. [Alex McLevy]

Angel Olsen appears on the Pitchfork lineup so regularly now that she could front a house band with Kurt Vile and the Animal Collective guys. But for as many times as we’ve seen Ms. Olsen live, in Union Park and elsewhere, we’ve never heard the same set twice. Beyond the evolution of her sound across her most recent albums—All Mirrors’ towering walls of synths and her EP of anesthetized ’80s covers—she has a way of transforming her studio work just enough to surprise at a live show. [Laura Adamczyk]

In each of St. Vincent’s distinct musical eras, she promises something new. Masseduction brought latex-clad minions and hyper-stylized images of femininity, combining her meticulous approach to live performances with a near-robotic element. With Daddy’s Home, she’s taken a dive into the ’70s funkadelic era, with a more relaxed air and lingering sensuality in her promos. As one of her first shows on tour, it will be interesting how she brings it to life on stage. But no matter what she’s doing, she shreds. [Gabrielle Sanchez]

It Is What It Is was one of the best albums of last year (and instant classic “Dragonball Durag” one of the best singles), and activities like his Adult Swim-prompted collaboration with Ariana Grande have kept idiosyncratic artist Thundercat firmly in the spotlight. But really, there’s no need for any additional reasons to check out the one-named wonder beyond his glorious—and gloriously funky—self. Thundercat is his own justification. [Alex McLevy]

What, like you’re going to make Erykah Badu the final-day headliner of your music festival and expect anyone to not be enthusiastic? This is the kind of above-the-title artist that we’d go out of our way to see in any setting, but there’s something about the idea of Badu taking the stage just as the sun has set on a warm Chicago evening that feels especially right. Our heads might instinctively champion many of the smaller acts performing this weekend, but our hearts belong to Erykah Badu. [Alex McLevy]