Roots Picnic: What to see and hear, besides Dave Chappelle and the Roots

The 2023 Roots Picnic is upon us.

The Philadelphia hip-hop band’s ever-expanding annual festival begins Friday night, with Dave Chappelle and the Roots sharing the stage at the Wells Fargo Center.

Then on Saturday and Sunday, the Picnic moves back to its home base of the Mann Center, where it will occupy three stages in the Fairmount Park venue.

This year, the Mann grounds will feature the Roots Picnic food court, the Love + Grit Black Business Marketplace, and the Roots Picnic Spades Tournament with comedian Clint Coley, which debuted last year.

There’s lots of music to choose from. Memphis rapper Glorilla, Philly rapper Fridayyand D.C. go-go specialists Rare Essence and Backyard, and Philly bandleader Adam Blackstone with gospel singers Mary Mary and Coco Jones are at the fest Saturday.

Miami hip-hop duo City Girls, jazz-classical ensemble Yussef Dayes Experience, and Philly duo Kindred the Family Soul play Sunday.

Here are 10 picks on what not to miss at this year’s Picnic.

2023 marks the 50th anniversary of hip-hop. It’s also the 25th anniversary of The Miseducation of Lauryn Hill. The 1998 debut solo album by the Fugees singer and rapper was the first hip-hop album to win an album of the year Grammy. The soul and rap classic, which features the Roots’ James Poyser on seven songs, is still Hill’s only studio album. Hill will perform it in its entirety, from “Lost Ones” to “Everything is Everything.” Over the years, she’s developed a reputation for tardiness, so hopefully she’ll be on time as well as on point.

The Philadelphia rapper born Symere Woods pops over to Philly’s other hip-hop festival after years of being a regular at Jay-Z’s Made in America. Uzi is overdue for new music. The adventurous emo and sometimes mumble rapper’s last proper solo album was Eternal Atake, which came out in 2020. Uzi is the most successful Philadelphia artist of the Spotify era, with two songs, “XO Tour Liif3″ and “Lucid Dreams,” with over 1 billion streams. His latest hit, the oddly structured “Just Wanna Rock,” is a slow-burning hit getting plenty of play at Philly sporting events.

In the late 1990s and early 2000s, the collective of neo-soul and hip-hop artists that included J-Dilla, Erykah Badu, and Bilal, as well as Questlove and Poyser of the Roots, were known as the Soulquarians, teaming up on records like Common’s Like Water for Chocolate and D’Angelo’s Voodoo.

Now, Soulquarians sets with Questlove and Poyser, and musicians like Philly bassist Adam Blackstone (who is also performing separately) have become a Picnic tradition. The band will be joined by the Isley Brothers, the “Twist & Shout” and “Fight the Power” legends with singer Ronald Isley, 82, and his guitarist brother Ernie, 71. Roy Ayers, the much-sampled vibes player originally on the bill, will not be performing.

Beanie Sigel is the definition of a rapper’s rapper, a command presence with unassailable street cred — named after a street in South Philly — who served as Jay-Z’s right-hand man back in the early 00′s. That was the era in which, Sigel, Freeway, Peedi Crakk, Oschino & Sparks, and Young Gunz (collectively known as State Property), made a hip-hop gangster movie, and scored hits like the Young Gunz classic “Can’t Stop Won’t Stop.”

Sydney Bennett, formerly known as Syd tha Kid, and now just plain Syd first came to notice over a decade ago as a member of the Odd Future collective, along with Tyler the Creator, Earl Sweatshirt, and Frank Ocean. In those days, Syd was known primarily as a DJ, then revealed herself to be a canny, seductive singer in the band The Internet, along with collaborator Steve Lacey. On her two solo albums, 2017′s Fin and last year’s Broken Hearts Club, she’s distinguished herself with disconsolate love songs that are smooth on the surface and cut deep with a surplus of hurt.

Diddy dropped the ball, and Usher saved the day. The plan for this year’s Picnic was for the Roots to pair off with Sean “Diddy” Combs as they did with Mary J. Blige last year. But with Diddy dropping out “due to unforeseen circumstances,” he’s been replaced by marquee headliner Usher Raymond, the “Yeah!” hitmaker who turned out to be between Las Vegas residencies, and available. On such short notice, the Atlanta entertainer won’t be pulling together a show with the Roots, but will be bringing his own stage show with him.

One of the Picnic’s annual highlights is this showcase, with DJ J. Period backing Black Thought as the Roots rapper goes head to head with other estimable MCs. This year’s throw down includes a Philly classic who’s rarely heard from these days in Eve, plus Busta Rhymes, the motormouthed Native Tongues rapper who stole the show at the Roots-helmed 50th anniversary of hip-hop celebration at this year’s Grammys.

One highlight of last year’s Picnic was a Sunday afternoon set by Kirk Franklin plagued by sound problems which forced Franklin’s singers to rouse the crowd without amplification. This year’s big name gospel booking is Maverick City Music, the Atlanta-born worship music collective. Kingdom: Book One, the group’s 2022 album, is a collaboration with Franklin and the singers of the Florida Correctional Institute that swept all four gospel and contemporary Christian awards at this year’s awards.

Neo-soul singer Ari Lennox’s Age / Sex / Location simmers, conjuring an early Erykah Badu vibe from the opening “POF” that Lennox rides throughout as she looks for more than sensual satisfaction on her second full-length album on J. Cole’s Dreamville label. The D.C.-born singer broke through with the title cut to her 2019 Shea Butter Baby, and as with Badu, you can hear Billie Holiday in her music.

The Picnic podcast stage is recommended not just because it’s hosting some of the biggest names in the hip-hop adjacent podcast game. Those would include Charlamagne Tha God, Don’t Call Me White Girl, People’s Party with Talib Kweli, DJ Akademiks, and of course Questlove Supreme. The live pods are taking place high up on the hill on the Skyline Stage, where the crowds are thinner, the hassles are few, and lines at the food trucks shorter.

More information at rootspicnic.com