How the Roots Picnic Became Hip-Hop’s Greatest Festival 

On an early Saturday evening in Philadelphia, in a pastoral stretch of park known as the Mann Center for the Performing Arts, Questlove is making time stand still. Onstage with him are Ronald Isley, wearing a patent-leather suit and looking ageless enough at 82 to make you think of Dorian Gray; Ernie Isley, playing a guitar solo with his teeth at a comparatively youthful 71; and the rest of the current-day iteration of the Isley Brothers, along with Questlove’s Roots bandmate Captain Kirk Douglas on guitar.

As Questlove begins playing the instantly recognizable drum pattern for America’s horny national anthem, “Footsteps in the Dark,” it’s clear that musicians like himself and Kirk aren’t strictly needed to handle these lovely, ancient compositions. But they’re up here nonetheless, keeping time and playing simple rhythms, despite being spread thin on what is probably the busiest weekend of their year, the three-day Roots Picnic. It’s obvious that they’re playing for fun, and for love.

The Roots first brought this festival to the band’s hometown in 2008, a lifetime ago for some of the people in attendance this year. “Take my daughter, for example, who’s 17 — this is all she knows as an indication of the beginning of summer,” says Tariq Trotter, a.k.a. Black Thought, when I reach the virtuosic Roots vocalist via Zoom from his backyard in Maplewood, New Jersey, a few days before the Picnic. “It’s just wild to think about… When we were holding the picnic on a hot slab of concrete, we aspired to one day be able to have it on a festival grounds like this one.”

This year, the festival boasted performances from Ms. Lauryn Hill (who ended up bringing out the rest of the Fugees), Lil Uzi Vert, Usher, Eve, Busta Rhymes, Ari Lennox, City Girls, GloRilla, and a reunion of the early-2000s Roc-A-Fella crew State Property that was the highlight of the lineup for every online rap head of a certain age. “This is a family affair,” Trotter continues. “That’s the vibe. But you know what’s crazy? Some of the artists that we bring out — people who I would think tend to perform for predominantly Black audiences on a larger scale — when they come out to the Roots Picnic, they’re in awe. It’s breathtaking for them to see that many Black people together in the city of Philadelphia at one event.” 

In 2008, the Roots were already starting to think about the type of career shift that would make them the house band for The Tonight Show Starring Jimmy Fallon a few years later. But before they traded a life of constant touring for a steadier gig, they wanted to accomplish everything on their bucket list — which included their own music festival, a dream that dated back to the Nineties.  “At the time, you only knew about Woodstock, Live Aid, Farm Aid, and Lollapalooza, where there was little room for Black culture,” says Questlove, a.k.a. Ahmir Thompson, who’s on the Zoom with Trotter and their longtime manager and current Live Nation Urban president Shawn Gee. “For Black people, there were always the cool jazz festivals, and that’s it. But when we got to Europe, it was way more eclectic and diverse. Our minds were blown. It was always, ‘Wouldn’t it be dope if we could bring this sort of thing back to the United States?’”

The first few Roots Picnics were smaller gatherings, where ticket sales were seemingly trumped by the massive guest lists. Fifteen years later, they sold upwards of 55,000 tickets to what is now a Philly institution. Walking the grounds on the festival’s first day, I see people dressed down for a cookout, and others who are dressed up for something akin to an all-day, outdoor, mid-Atlantic Met Gala. There are stocky self-identified Muslims with freshly manicured beards and shape-ups, and women with face piercings and chunky blonde dreads.

Events like the Roots Picnic are no longer alone. The market finally came to its senses and woke up to tremendous earning potential of more diverse types of festivals and arena shows. This is both a blessing for fans, and a challenge for established events like this one, who have to remain innovative and dynamic to compete. For the Roots, it meant doubling down on their principles. “As other festivals came into the market, we looked at what was not being served in the city of Philadelphia, and it was Black culture,” Shawn Gee says. “So we went deep into Black culture over the last couple of years, specifically mirroring the various genres of Black music that traditionally aren’t showcased at festivals.”

Something the Picnic has been remarkably successful in doing is cultivating a brand and a culture. Trotter, Thompson, and Gee book artists who serve as a reflection of their own eclectic taste and sense of history.  When I attempt to articulate the quality that bonds the R&B divas, mixtape rappers, and soul legends that populate every Roots Picnic as the “thinking person’s” ideal of each genre, Ahmir puts it more directly: “They’re nerds.” It’s a bill full of disparate genres, separated by continents and generations, but united in a thoughtful, intellectual approach to their work, and the thoughtful, intellectual fanbase they’ve cultivated.

“You want to make sure you got the barbershop covered, people from the generation that hung around barbershops and would have four-hour conversations about a particular album,” Thompson continues. “Within the Roots circle, we are actually our demographic.” 

“If there is a macro theme that even subconsciously went into the planning of the festival this year, it’s Philadelphia,” Trotter adds. “This is really the hometown music experience on every different level.” 

Case in point: the momentous Saturday-afternoon reunion of State Property, the nerd’s favorite 2000s street-rap collective. The group made Philly a hotbed of talent around the turn of the century with their brand of alternately introspective and menacing (but always fun and radio-friendly) rap. It was a mixtape-era set, with most of the songs being performed over different beats (e.g. “Feel It in the Air” over “In the Air Tonight”). The loudest cheers and most love went to Sigel, State Property’s founder, point guard, and star quarterback. He played the set’s host, calling his group members to the stage one by one, each getting a showcase song and a hero’s welcome. 

Beans and Freeway in particular have suffered harrowing personal and health-related tragedies over the last decade. The crowd was overwhelmingly supportive and appreciative as Beans fought through his verses, a lovefest thanking the collective for their indelible body of work, and the moment when they briefly put Philly on top of rap.

The slate also had room for a generation of Philly acts raised in the shadow of the Picnic. When Lil Uzi Vert played his first Roots Picnic in 2016, he was literally on the bottom line of the flier. By his next visit in 2018, he had made the middle; this year, he was one of the headliners.

Uzi justified his placement in the massive crowd he drew, which far exceeded the ostensible headliner, a densely standing crowd one football field across and two football fields deep. As a rapper, Uzi arguably has more in common with Hayley Williams, with whom he shared a stage at Madison Square Garden the previous weekend, than Black Thought — but one thing the two MCs do share is the ability to command a stage. Uzi brought energy and sang well and clearly over his turned-down vocals for a crowd that didn’t do much to match his energy, because they were busy trying to keep their phones steady, held in their outstretched arms overhead. 

After Uzi, the crowd began to stream out, perhaps a casualty of too much sun and too many substances, par for the course at any all-day festival. What they missed, unfortunately, was an all-time Lauryn Hill set. She was barely 15 minutes late, practically early by her standards, and she brought at least a 20-piece band with her. She was crisp, well-rehearsed, and maintained supreme professionalism, bringing out Wyclef and Pras for a surprise set of hits off of The Score.

Through it all, Hill kept shouting out Philly and her history with the city as a New Jersey native. She talked about her bond with Roots, describing them as members of the same graduating class as herself in the music industry. At one point she shouted out Ruffhouse Records, the Philly imprint that first signed the Fugees. Questlove grabbed a mic to add that he once interned there. It was the banter of two old friends catching up. 

Nothing about the Roots Picnic feels under-considered — it’s a festival where every detail comes together. Take Trent, the Philly-based chef/restaurateur who began with a food truck called Lil Trent’s and a dream. He was brought in to cater backstage at the Picnic in 2014 as he was beginning to build his brand, and his business has grown in the subsequent years along with the festival. 

“He reaches out every year and thanks us, because he says his experience at the Picnic helped grow his business,” Shawn Gee says. “It’s that same element of giving back to the folks of Philadelphia, from where the three of us come from. We want that across all elements of the Picnic. Music, everything.  All of the experience. One thing I always make sure of is, who are the Black entrepreneurs in Philadelphia that are getting this opportunity that they don’t at other festivals?”