The sun has set at Afropunk, Brooklyn’s annual festival celebrating black music, and the crowd is agitated. A giant banner to the right of the stage reads: “NO SEXISM. NO RACISM. NO ABLEISM. NO AGEISM. NO HOMOPHOBIA. NO FATPHOBIA. NO TRANSPHOBIA. NO HATEFULNESS.” Lauryn Hill, one of the festival’s marquee performers, was due onstage 45 minutes ago. When Hill performs these days, there is a looming fear that she’ll show up hours late, if at all. But this is a tightly scheduled event, and Grace Jones is set to follow. When Hill finally emerges, the fact that she’s only 45 minutes late—her set will be cut short, but she will play—feels like a blessing.

Clad in a floor-length white coat atop a fire-red dress, her hair cropped close to her head, Hill sits on a stool in front of her band and begins to strum an acoustic guitar. The sound system is far too quiet, and these songs—noodling renditions of songs from 2002’s MTV Unplugged No. 2.0, her collection of raw, religious acoustic sketches—are evaporating. Most of the crowd struggles to see or hear her, and fans begin to initiate chants of protest against the crappy conditions before giving up and milling around, bored. Rumors swirl that Hill will show up at a Boiler Room DJ set later tonight, but she doesn’t.

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That evening in August found Hill and her fans in a familiar suspended state, trapped somewhere between anticipation, reverence, confusion, hope, and defeat. More than any icon in recent history—excluding Dave Chappelle, maybe—Hill has been shrouded in mystery and misinformation. She has produced only a handful of new tracks since her ground-shifting breakout, 1998’s The Miseducation of Lauryn Hill, and has faced a mountain of back taxes that landed her in prison in 2013. She has developed an inconsistent live reputation, delivering a brilliant set one month and then bailing on a show the next. Bring up Lauryn Hill in a casual conversation and you’re likely to incite speculation that she is crazy, or hear references to her politics, which are often perceived as militant.

Hill has become an inscrutable kind of icon whose career begs the most dramatic questions we have about art and celebrity. What do artists owe their fans? What do those fans owe the artists? Is fame the equivalent of captivity? At what point does conviction come at the expense of creative output? Can an artist—a black female artist—participate in the entertainment industry purely on her own terms?

Hill’s reputation as a tormented recluse obscures what’s actually happened in recent years, which is more than meets the eye. Since 2010, she has been working quietly and diligently on a new album and a host of politically minded film projects. She began touring again five years ago as a way of exercising artistic muscle and financing her recording plans, says Phil Nicolo, one of her current producers and a founder of Ruffhouse, the Fugees’ original label. According to Nicolo, she is closer than ever to finishing the follow-up to Miseducation. And thanks to her involvement in a documentary about the late Nina Simone—perhaps her greatest forebear—Hill is on the brink of a genuine comeback. With world politics dovetailing with pop culture in an unprecedented way, there couldn’t be a better time.