Ms. Lauryn Hill at her 2018 Pitchfork Music Festival performance | Photo by Nelson Okunlola (The TRiiBE)

Ms. Lauryn Hill actually showed up – quieting a collective fear that she would arrive more than an hour late to her 85-minute Pitchfork Music Festival set or not show at all. Just a few nights before, fans complained about the 43-year-old hip hop legend rushing through her setlist after being an hour or so late to the Toronto stop of her 20th Anniversary of The Miseducation of Lauryn Hill tour. It’s a reputation she’s acquired after years of tardiness and no-shows, which she’s blamed on a need to align her energy before performances.

But the Hill that showed up Sunday night still didn’t feel quite right. She appeared at war with her own perfectionism: at times, wildly motioning for her sound engineer to fix her mic levels, for her band to drop out sporadically during bridges and for her background singers to fill improvised arrangements with detailed harmonies.

Her struggle seemed larger than performing her one-and-only solo album to the crowd’s liking. It felt like a glimpse into the mind of a creative treasure, one gifted with a divine charge to deliver a flawless piece of art on the first try, who then had to live with the immense pressure of topping herself for the last 20 years.

“This charge was in me so heavily. I didn’t sleep. I didn’t rest,” Hill said, taking a few moments to discuss the making of Miseducation with the audience. “I realized this album, it has a life outside of me. Beyond me. It’s the people’s music.”

Deuces, fam | Photo by Morgan Elise Johnson (The TRiiBE)

The three-day festival got off to a rainy start on Friday afternoon. Chicago’s own Saba brought out the sunshine, though, with a therapeutic performance of his critically-acclaimed second album, Care For Me.

“This shit is so amazing. I’m so blessed to be here,” Saba said about his first time on the Pitchfork stage. He rolled through “Calligraphy” and “Fighter” with his fans reciting the lyrics back to him.

“I wanna do my favorites from Bucket List,” Saba continued.

The crowd roared as he cruised through the deep cuts: “Photosynthesis,” “Church/Liquor Store,” and “MOST.” He took a break in the middle of his show to talk about his cousin and best friend, John Walt, who was fatally stabbed last year in the River North neighborhood. According to Saba, his cousin died two weeks before his first headlining tour.

Saba instructed the crowd to say, “Long Live John Walt,” as the beginning of Care For Me’s “Prom/King” played in the background. He didn’t rap any of the words to the heartbreaking track, instead the deejay cut straight to the last line of the song: “I just hope we make it to tomorrow.”

Saba brought the whole Pivot Gang on stage | Photo by Nelson Okunlola (The TRiiBE)

On Saturday, a 3 PM Chicago Comedy Set at the Bookfort tent featured comedians from all walks of life, including emerging funny Black woman Ashley Ray. During her 10-to-15-minute set, Ray joked about being the only light-skinned child in her family with her mom, who she referred to as ”pussy printer,” disclosing that she “ran out of ink.”

Just after 5 PM, legendary singer, producer and songwriter Raphael Saadiq took the red stage. He gave the crowd a taste of some new music from his upcoming album, Jimmy Lee, which is scheduled for a winter release, he said. Saadiq then sped through a few of his jams, such as “Anniversary” from his days as a member of Tony Toni Tone and “Be Here” from his solo album Instant Vintage, trying to see which songs would stick to the predominately-white audience.

Once he played “Cranes,” a song he wrote and produced on Solange’s A Seat At The Table, he teased: “Y’all don’t know the words.”

The moment was telling of the overall Black experience at Pitchfork, a festival rooted in alternative music. Saadiq is an artist whose music lives in the neo-soul nostalgia of the 1990s. His versatility in creating instantaneous cravings for love on any song he’s a part of is why he’s the mastermind behind the musical choices of Issa Rae’s Insecure on HBO and that of neo-soul sensation D’Angelo.

Yet, Saadiq and other 90s artists like him who now peruse the white festival crowd rarely get the same family reunion reception as they would at a Black festival such as Essence Fest. Meaning, there won’t be the Black aunties seductively dancing to their jams, or Black couples making eyes at each other while singing along to their love songs.

Raphael Saadiq at his Pitchfork performance | Photo by Morgan Elise Johnson (The TRiiBE)

“The energy’s definitely different. I know I was really excited to see Solange and A Tribe Called Quest last year,” said Paige Fraser, a professional ballerina in Chicago. Last year, Solange closed out Pitchfork with a beautiful ode to Black women and life, attracting hundreds of Black folk to the festival on Sunday alone.

“Chicago is lacking that [diversity],” she said while waiting on Kelela’s performance Saturday evening. “You feel it, and the artist feels it. It affects the energy, the vibe.”

On Sunday, South Side natives Leah Isiael and Trey Taylor felt the same way. They bought one-day passes for Sunday to see the back-to-back home team lineup of Ravyn Lenae, Smino and Noname.

By the end of Noname’s set, where she brought out Saba, Lenae, Smino and Joseph Chilliams as a testament to the future of Chicago hip hop and R&B, Isiael and Taylor realized that the ability of these artists to relay the hardships of being Black in Chicago to white audiences through consumable music is major – but, it doesn’t mean that white folks feel the lyrics in the same way Black listeners do. Also, of course, there is the constant paranoia of hoping the white people around you don’t say the word, “nigga,” when singing and rapping along.

Trey Taylor & Leah Isiael waiting on Lauryn Hill | Photo by Morgan Elise Johnson (The TRiiBE)

“Noname could’ve did this on the South Side and it would’ve been a family event, but you gotta  branch out. You want everybody to hear your stuff so you come here and do your thing,” Taylor said.

For a song like “Diddy Bop,” off Noname’s 2016 debut mixtape Telefone, the words narrate the juxtaposition of having to stay with cousins because mom couldn’t pay the light bill this month with the joy of dancing at family reunions and block-club parties during summertime Chi.

“I mean, it’s obviously a lot more white people so they know her music but they not really familiar with the message behind it,” Isiael said. “They just reciting words. They not really understanding that shit.”

As the evening wound down, some fest goers camped out near the Chaka Khan stage, hoping to grab a spot with the perfect view, while Dram jumped in the crowd at the neighboring green stage to sing his hit “Broccoli.”

Khan entered the stage with crazy applause. She led the crowd through super funky renditions of “Everlasting Love,” her 1977 song with the band Rufus, and “I’m A Woman,” from her 1978 solo album debut, Chaka. With the latter, her band added hints of reggae to the beat, which made for a fun time.

Chaka Khan during her Pitchfork performance | Photo by Morgan Elise Johnson (The TRiiBE)

At times, Khan lent her spotlight to the members of her band and the audience. She handed the bridge section of “Sweet Thing,” undeniably the best part of the track, to one of her three background singers, and let her guitarist close out “Ain’t Nobody” by making love to his guitar for his solo. On “Tell Me Something Good,” she teased out the chorus, asking the men in the audience to sing to the women and vice versa.

“Everytime the fellas sing, I can’t handle that,” Khan said.

Hill’s stage lit up around 8:30 PM. Though her set was scheduled to begin at 8:25 PM, her deejay appeared and started playing an array of hip-hop hits, including Kanye West’s “Get Em High” and Dr. Dre’s “The Next Episode.” At one point, he spun her collaboration with Nas, “If I Ruled The World,” and everyone cheered thinking Hill was coming out, but she didn’t.

Around 8:55 PM, Hill hit the stage: “This is a special moment, you know. It’s been 20 years.”

She jumped right into “Lost Ones,” followed by “Everything is Everything.” Everyone rapped and sang along. On the stage backdrop, there were flashing archival images of Black life, including kids graduating from school. It seemed like Hill was back to her old self. Even Chance the Rapper flashed across the jumbotron, singing “To Zion” from the bottom of his heart.

Lauryn HIll during her Pitchfork performance | Photo by Nelson Okunlola (The TRiiBE)

However, she started losing the crowd with a drawn-out version of “Final Hour,” which could’ve been shortened to a medley to make room for more Miseducation essentials, such as “Can’t Take My Eyes Off of You,” or perhaps songs she sang as a member of the Fugees or even songs she worked on behind-the scenes, such as Mary J. Blige’s “All That I Can Say.”

She clearly had more to give, leaving everyone wondering how epic a moonlit night of Ms. Lauryn Hill truly could have been if she had better time management with her improvisation and no park district curfew.

Around 10:15 PM, Hill rounded out the night with “Doo Wop (That Thing).” She also stayed behind to take pictures with fans and other Pitchfork artists backstage.

“I just want to thank you. Thank you for sharing this important moment with us,” Hill said. “I thank you for your support. I thank you for your love. And if this album touched your soul, it’s because the universe gifted you with this music.”