Stretching their wings has long been a calling card for the Roots, the Philadelphia-born, dynamically live hip hop band. Experimenting with R&B is what won them their biggest-ever, Grammy-winning hit, “You Got Me” (featuring Erykah Badu and Eve). Toying with the mainstream and becoming the house band for NBC’s “Tonight Show with Jimmy Fallon” put them in people’s homes performing new music on a nightly basis.
One of the group’s longest-lasting and most popular experiments is the Roots Picnic: their hometown musical and cultural mini-festival. Started as a one-day, outdoor multi-genre event on blacktop in 2008, the Roots Picnic expanded, by 2019, into two days on real grass at Fairmount Park’s Mann Center.
For 2023, The Roots expanded its Picnic beyond grass (and its usual two-day schedule) with an additional pre-Mann nighttime event in an indoor arena with comedy as its lead, headlined by friend and collaborator Dave Chappelle. The Roots also ceased its usual practice of the full band backing the weekend’s headliners, until its surprise pairing with Lauryn Hill’s set-ending mini-reunion with her fellow Fugees, Wyclef Jean and Pras Michel. (To be fair, Diddy and the Roots were a headline pairing until the rapper-mogul pulled out at the last minute and Usher picked up the Picnic torch.) By weekend’s close, the 2023 iteration of the Roots Picnic wound up being its most thoroughly engaging, and surprise-filled festival.
Controversial comedian Dave Chappelle and the Roots have long been collaborators. Along with Questlove (and John Mayer for a cover of the “Diff’rent Strokes” theme song) guesting on Comedy Central’s “Chappelle Show,” and the band taking part in the 2005 movie “Dave Chappelle’s Block Party,” Chappelle was scheduled for 2018’s Roots Picnic until inclement weather dashed all comic hope. For the 2023’s Roots Picnic’s first-ever indoor arena show at Philly’s Wells Fargo Center, Chappelle and the Roots co-headlined the nighttime jam for the band’s only full showcase of the weekend.
The Roots were tight and briskly inventive. When Black Thought wasn’t smartly speed-rapping his way through the “Rage is Back” freestyle and his part of “You Got Me” (with guitarist Kirk Douglas doubling impressively as vocalist), the ensemble was a churning combine of insistent rhythm (Questlove, together with percussionist Stro Elliot and bassist Mark Kelley) and dexterous heavy riffing from Douglas and sousaphone player Tuba Gooding Jr. As for Chappelle, despised by the trans community for his rough comedic treatment, he barely stuck to his part of the mean-edged bargain.
While keeping on the pro-trans tip in relation to one-time University of Pennsylvania swimmer Lia Thomas (“Let the bitch swim”), Chappelle saved disses for disabled North Carolina U.S. Rep. Madison Cawthorn and his Filipino-American wife. Most surprising about the comic portion of the program were the guests that Chappelle had on stage – “Saturday Night Live” Weekend Update co-anchor Michael Che and one-time Daily Show icon Jon Stewart, who ended his set with anti-gun jokes about the paperwork of buying AR-15 rifles being easier than adopting pets.
The end of the second night of the Roots Picnic got a huge surprise when Saturday headliner Lauryn Hill welcomed one-time Fugees bandmates Wyclef Jean and Pras Michél for a brief, but impactful reunion of the hit-making R&B-hip hop trio. Handsomely dressed for the surprisingly cool breezes of June with an emerald green cape and a gem-encrusted vest-shirt-and-tie ensemble, Hill started her set by promoting the 25th anniversary of her 10 million-plus selling “The Miseducation of Lauryn Hill” (“I love saying those words,” she shouted) before launching into husky-voiced renditions of “Everything Is Everything” and a jaunty “Superstar.”
Not long after covering Frankie Valli’s “Can’t Take My Eyes Off You,” and a spirited take on her solo classic, “Doo Wop (That Thing),” Hill was joined by players in the Roots, and her Fugees friends Pras and Wyclef. Starting with “The Score” and ending with the hoarse, but sing-song-y “Fu-Gee-La,” the set-within-a-set seemed like a fully-rehearsed, crisply executed session as opposed to an impromptu, last-minute thing. Perhaps the intuition of three old souls interacting as one, the frisky Fugees ran through the huff-and-puffing “How Many Mics,” a raga-tinged “Zealots,” and the rugged rhymes and supple rhythms of “Ready or Not” and “Killing Me Softly with His Song,” before its unified “Fu-Gee-La” finale.
Beyond its shock value to an audience hung on every Hill trill, was the fact that the reunion happened at all, taking into account Pras’ recent conviction for conspiracy to defraud the U.S. Crediting Philly’s Ruffhouse Records’ Chris Schwartz and Joe Nicolo for signing Fugees and Hill in the first place, Hill shouted out Questlove (who interned at Ruffhouse as a kid) and the Roots for making “this class reunion” happen.
The Roots’ backing of modern R&B legends (e.g., Mary J. Blige, Pharrell) has forever been the most unique element of the Picnic. That job, this year, however, was left to Questlove’s occasional other ensemble, Soulquarians, playing behind, the Isley Brothers. While guitarist Ernie Isley managed a few patented flanged, fuzztone squiggly solos, the heavy lifting during their quiet storming set came down to vocalist Ron Isley. Resplendent in his “Mr. Big” gear of a gold, gilded suit jacket and a black chapeau (in the afternoon’s 80-degree heat, no less) Ron Isley used the top of his bold falsetto for romantic classics such as “Between the Sheets” and an acoustic version of Todd Rundgren’s “Hello, It’s Me.”
This writer’s favorite act of Made in America 2022,the Memphis-based GloRilla, traded her cheerleader outfit for a glammy purple sparkle jumpsuit, and managed to make hers the most energized set of the Picnic. Along with summertime anthemic hits such as “Tomorrow 2” and “F.N.F (Let’s Go),” GloRilla raged forward, frenetically, with contagious should-be-hits such as “Unh Unh” and “Internet Trolls.” Somebody please get GloRilla a headlining set, soon.
Nothing is more personal to the Roots’ co-founding mouthpiece than a great flowing freestyle. So fast and loose – but studied – is Thought when it comes to the art of improvisational rapid-fire rapping, he surely freestyles in his sleep. That’s what made the 2023 Mixtape Session with Busta Rhymes so special, as this was two men with the power, breath control and jazz of fast-paced rap at their command. While Thought ran through elements of the passionate “Act Too (the Love of My Life),” Busta stuck to barking and teasing his way through his rugged, hop-pop classics such as “Put Your Hand Where My Eyes Could See.” As for Eve – the “First Lady of Ruff Ryders,” a Philly-born native – she traded mean licks with Black Thought, returned to her Gwen Stefani pop duet days with “Who’s That Girl?” and paid tribute to the late, great DMX with a portion of their 1999 track “Ruff Ryders’ Anthem (Remix)” that sounded as fresh as if was recorded yesterday.
While Philadelphia rapper-fashionista Lil Uzi Vert has been part of the Roots Picnic in the past, he hasn’t been to the fest’s mainstage since long before his having a Top Ten hit (“Just Wanna Rock”) or going emo with recent on-stage collabs with Paramore at Madison Square Garden, or dropping tracks with Bring Me the Horizon (“AmEN!”). Resplendent in a heavily decorated jeans jacket, Uzi ran through a diverse array of steely, mechanized rhythms and fast FX-filled vocals on his own hits (“Sauce It Up,” “That’s a Rack”) and covers (a hearty version of Migos’ “Bad and Boujee”). After inviting everyone onstage to dance – only to have stage management immediately kick fans offstage – Uzi punked up “XO TOUR Llif3” and “Just Wanna Rock” with aggro energy and robotic voice-processed zeal.
After a touching video tribute to Philadelphia electro rapper and singer PnB Rock (murdered in LA in 2022), glossy R&B vocalist and dancer Usher ran through a brass-driven set of his classics, slow (“My Boo,” “Confessions”), dramatically mid-tempo (“Caught Up,” “U Got It Bad”) and grooving (“Birthday”).
Dressed in what looked like a body-hugging black-and-white two-piece, Usher twirled, kicked and arched his body like Michael Jackson on hyper-drive while lending each vocal phrase an almost impossible brand of passion for someone moving so physically and so fast. By set’s end, however, Usher changed into something relaxed – red leather – and welcomed Grammy-winning, Philadelphia R&B vocalist Jazmine Sullivan and Black Thought in freestyle verse, some sensual vocal spieling and chilled-out dance moves between the vocalists. While Black Thought did not get in on the dancing, the meetup between Sullivan and Usher was yet another surprise set ender, and a reminder to fans that – when it comes to the Roots Picnic – leaving early means missing the best parts of the festival.