Dave Chappelle and the Roots, and Jon Stewart and Michael Che, kick off the Roots Picnic at Wells Fargo Center

The Roots Picnic grew into a two-day event at the Mann Center in 2022, and on Friday the Philadelphia hip-hop band’s festival debuted a more expansive full-weekend look with a sold-out show at the Wells Fargo Center in South Philly.

The draw? A double bill hosted by the Roots, the group led by rapper Tariq “Black Thought” Trotter and drummer Ahmir “Questlove” Thompson, who played their first full set in the city of their birth since before the pandemic.

They were joined by Dave Chappelle, the comedian who has been criticized of late for remarks perceived to be transphobic, with whom the Roots have a long shared history. And as an added bonus, the show included a pair of big-name surprise guests.

The Roots-Chappelle relationship dates to the turn of the century, when, as Chappelle recalled during his headlining set, he watched Questlove selflessly support such artists as D’Angelo and Common. Questlove was a guest on Chappelle Show skits and the Roots were the house band in the 2005 movie Dave Chappelle’s Block Party.

Chappelle was scheduled to headline the Picnic in 2018, but his set was cut short due to severe weather. Last year, he dropped in at a pre-festival show at Punch Line Philly.

But Friday’s Wells Fargo show was by far the festival’s biggest comedic foray, complete with special guests that made it even bigger than advertised.

And it arrived with an air of mystery, in part because, as is common with comedians, no cell phones were allowed, and thus no social media sharing of valuable jokes or controversial remarks.

Access was not provided to the media. The Inquirer paid its own way in. Fans who brought phones had them placed in a pouch they kept with them but were unable to open until after the show.

If your ticket was on your phone, staffers scribbled seating info on a Post-it note sized piece of paper, which functioned as a ticket. I left my phone at home for fear of delays and printed out my ticket.

But the process seemed to work seamlessly, with added benefits. Being freed from an addictive device, and not being annoyed by other patrons snapping photos. (Mea culpa, in many cases.)

The 3½-hour show — presented in the round, though the stage was square like a boxing ring — began with a surprise set by Saturday Night Live writer and “Weekend Update” co-host Michael Che.

DJ Trauma spun hip-hop hits between acts; comic Marshall Brandon did a short, amusing set. His best observational joke was about how houses in Philadelphia are so close together you can open your window and reach into your neighbor’s refrigerator.

And then there was a major surprise. Between the Roots and Chappelle’s sets — each an hour in duration with no shared time on stage — Jon Stewart was announced.

The Central Jersey resident said Chappelle and the Roots were among the few things that could get him to “drive my old a— down the turnpike.”

The 60-year-old comic riffed on how decrepit he is, including needing reading glasses to look at porn on his phone. (Ewww.) He closed with an excellent routine about how it’s easier to buy an AR-15 rifle than adopt a cat.

The Roots were spectacularly good. Their taut, propulsive set, anchored by Questlove and bassist Mark Kelley and demonstrating Black Thought’s how-does-he-do-it? breath control, did not let up. That went for “The Next Movement” from 1999′s Things Fall Apart on through their biggest hit, “You Got Me.”

The latter was a showcase for Kirk Douglas, both vocally and on lead guitar, while other stars were sousaphone player Tuba Gooding Jr. and Stro Elliot, who performed a mind-blowing electronic percussion solo.

It felt like a privilege to see the band together as a cohesive unit. Members are to appear in various configurations over two days at the Mann, but they don’t have a performance scheduled as “the Roots.”

And what about Chappelle? Was he funny? Offensive?

Both. Chappelle has come under intense criticism for his anti-cancel culture comedy, with his 2021 Netflix special The Closer earning particular condemnation from the trans community.

Friday’s show presented Chappelle with ample opportunity to make new enemies. He certainly didn’t back away from his reputation as an equal opportunity offender, and his button-pushing jokes got big laughs. He even mocked his Filipino American wife’s appearance — while also depicting her as cutting him down to size.

Chappelle remains a master of conversational comedy. He’s well prepared, but gives the impression of seriously thinking through his issues — such as how he feels about the Will Smith-Chris Rock slap, or when he was attacked at the Hollywood Bowl — in real time. It feels genuine. Stewart seemed off-kilter in comparison.

(That might have had to do with sound problems. During the sets by Che, Stewart and Chappelle, pockets of people in the lower bowl shouted that they couldn’t hear. It sounded fine upstairs.)

Anyone expecting Chappelle to double down was disappointed. “It’s Pride Month,” he said. “I’m not going to talk about those people.”

He didn’t quite keep his promise, but added that everyone he’s met with from the LBGTQ+ community “has been kind and respectful,” and blamed the characterization of the conflict as combative on a familiar target: the media.

Instead of talking about “those people,” he said he would make jokes about the disabled. A flurry about former North Carolina U.S. Rep. Madison Cawthorn followed.

Neither Chappelle nor Che could resist bringing up former University of Pennsylvania swimmer Lia Thomas, a favorite subject of anti-trans activists. But both comics came to the same conclusion, expressed by Chappelle: “Let the b— swim!”

Has Chappelle learned anything from his public and private conflicts with his critics? Mainly that it’s best to choose your battles wisely when you face a well-organized opponent.

Chappelle thanked the Roots profusely, expressed love for Philadelphia and said there’s little difference between the plight of Black people today and in 1863: “We just want to be free.”

He then finished by characterizing American life as a battle between red state “MAGA-land” and a blue state world whose name played on a homophobic slur. Given his druthers, he said, he’d choose to live in the latter.

The Roots Picnic continues at the Mann Center, 5201 Parkside Ave., on Saturday and Sunday. More information is at RootsPicnic.com.