Ms. Lauryn Hill at Pitchfork on Sunday night Credit: Sarah Joyce

It was coming up on 15 minutes past the scheduled 8:30 start time for Ms. Lauryn Hill’s headlining Pitchfork set when her DJ started playing Nas’s “If I Ruled the World,” which features Hill’s classic rendition of Kurtis Blow’s hook from the original—her cooing vocals over the itchy percussion of the song’s intro were met with thunderous anticipatory applause. But in moments it became disappointingly clear that this was not, in fact, the song that was going to introduce Ms. Lauryn Hill. A young photographer, not much older than me, came clamoring into the photo pit. “Damn, so she still hasn’t come out yet?” she asked, with a dash of genuine concern sprinkled on top of the obvious sarcasm. “Nah, but that was kind of a sick tease,” I replied.

A tinge of uncertainty had started to creep into the eyes of the fans in the front row, some of whom had been waiting to secure prime real estate since before Big Baby Dram played the same stage hours earlier. It looked a little like this:

Hill is notorious for a long string of late sets or straight-up missed shows, and as we entered the 20th minute with no sign of her, the question had to be in the back of everyone’s mind, if not in the front: Would this be another one? The DJ set, which also included DMX and Sister Nancy, set the perfect tone and successfully placated the thirsty crowd. Chicago was ready for Ms. Lauryn Hill.

Over my three days at Pitchfork, I heard people describe Hill’s imminent set as “a once-in-a-lifetime experience” so many times that it’d be pointless to attribute the quote to anybody in particular. It was clearly a sentimental thing to say, but technically it was also a fact—there’s never been and will never be again a chance to see Lauryn Hill celebrate the 20th anniversary of her only solo studio album at the Pitchfork Music Festival.

The crowd waits for Ms. Hill.Credit: Sarah Joyce

As the instrumental for “Lost Ones” began, a half-second of silence washed over what was clearly the weekend’s largest crowd. As Ms. Hill pranced onto the stage, wearing a sun hat and a billowing, diaphanous white skirt topped by an oversize plaid button-down, the park erupted. One of the people in that sea of waving arms and chanting voices was Chicago-based rapper Smino, who’d graced the same stage only a couple hours earlier.

“Lauryn Hill was one of the only rappers my momma listened to,” he’d told me earlier that evening. “With a single album, she was able to change the entire culture of hip-hop.”

Ms. Lauryn HillCredit: Sarah Joyce

Like many of the other performers of Pitchfork’s Sunday schedule, Smino is young enough to have grown up listening to and learning hip-hop in a post-Miseducation world. Hill is often credited with pioneering the rap-singing style where Smino now finds his own lane. In her performance of “Everything Is Everything,” she drifted seamlessly from spitting a cappella bars to singing extravagant, marathon runs that sounded as complete and vibrant as they did on the album two decades ago.

“It’s one of my favorite albums, and it’s been in my life since I was a kid,” said Nnamdi Ogbonnaya, another Sunday Pitchfork performer who’s just barely old enough to remember the album coming out. “It’s going to sound typical but ‘Doo Wop (That Thing)’ is still my favorite song off of it.”

For Chicago rapper Joseph Chilliams, who performed with Noname during her Sunday set, Lauryn Hill is just as significant as a symbol as she is an artist. “Just the idea of a black woman doing what she wanted, it’s important,” he said before Hill’s set. “On top of all that, she could rap and sing her ass off.”

It was an emotional night.Credit: Sarah Joyce

In an impromptu speech during her set, Hill spoke about the struggles she’d faced in bringing her solo debut to fruition after the breakup of the Fugees. “There were a lot of skeptics after I left the group. But I was so driven to get this thing done that I didn’t even sleep,” she said, raising her voice to a shout and sending an echo bouncing across the park.

The crowd favorite was probably “Ex-Factor.” It seemed like everyone was singing when the beat dropped out, leaving the harmonizing voices of the audience front and center to deliver the iconic chorus. South-side poet Kwynology, who says Hill is her favorite rapper, called it the perfect breakup song. “The way she was able to deliver a message about something so complex with such a simple melody is some true genius,” she said. “It’s black girl magic.”

The unheralded hero of the set was Hill’s use of imagery. Massive LED panels onstage set the mood for each song, and they showed us more than just the trippy light show you get at a typical festival. During her performance of “Everything Is Everything,” Hill used them to display images of black dancing and celebration: young women romping at skating rinks, b-boys spinning on the streets of New York, teenagers on corner-store runs carrying boom boxes.

Lauryn HillCredit: Sarah Joyce

During her sobering and emotional rendition of “Forgive Them Father,” she used the same screens to show video clips that’d been burned into our memory by infamous cases of police brutality, including the moments after Oscar Grant’s shooting, the seconds leading up to the murder of Walter Scott, and Sandra Bland’s encounter with a Texas traffic cop. Her visuals added to the intensity of some songs and to the high-spiritedness of others. She even used them to invoke a mellow nostalgia on “That Thing,” showing decades-old clips of her onstage.

Hill delivered everything you could’ve expected at her Pitchfork set: not just the amazing performances but also the eccentric outfit, the emphatic delivery and impromptu speeches, even the late start. It was enthralling, it was introspective, it was conscious, it was relentless, it was vulnerable, it was passionate, it was masterful, and it was fun. It was everything that makes The Miseducation of Lauryn Hill one of the greatest albums in the history of hip-hop, and it was the perfect way to celebrate the 20th anniversary of a classic.

Lauryn HillCredit: Sarah Joyce