Dave Chappelle — the bold-faced funny man who emerged in the early-2000s as an Afrocentric satirist, unafraid to squeeze risqué racial commentary into his now-legendary sketch comedy show — has long been an important figure in hip-hop. The first season of Chappelle’s Show (which briefly aired on Comedy Central) featured musical guests such as Mos Def, Talib Kweli, Busta Rhymes and The Roots, while its second included DMX, Erykah Badu and Kanye West (to name a few). Yet, unlike so many artists who haunt the primetime late-night sets of Jimmys (Fallon and Kimmel) — often seeming so out-of-context during their promotional performances that one wonders if the hosts even knew who they had invited — artists’s arrivals at Chappelle’s Show felt like pointed recommendations. Their performances served as punctuation marks for each episode.

So, a true Chappelle fan should not have been overwhelmingly surprised when hip-hop legends Ms. Lauryn Hill and Nas announced — just days before the launching of their joint PowerNomics Tour — that the notoriously-reclusive comedian would be joining them on the road. In fact, the closer that one has been paying attention, the less surprised they ought to be: Since June, Chappelle has performed aside Ms. Hill, Chance the Rapper, Childish Gambino and more during a residency at Radio City Music Hall; he has questioned Kendrick Lamar for Interview Magazine, an already-historic conversation in its own right; and he has continuously owned up to his role as a musical gatekeeper, like when he labeled Lil Wayne “one of the most clever motherfuckers ever” during an appearance on Sway In The Morning. Much like modern rappers, who can earn enough clout through their craft to eventually expand into other ventures (think fashion, film and Diddy’s Ciroc vodka), Chappelle became so deeply embedded into hip-hop through humor that his position aside two historic emcees just feels natural.

For anyone who’s ever nostalgically wondered how Chappelle’s Show accomplished its near-perfect roster of conscious Black musicians, or has hoped for a similarly prolific blending of hip-hop and comedy to occur today, the PowerNomics Tour — which touched down at the Michigan Lottery Amphitheatre at Freedom Hill in Sterling Heights on Fri., Sept. 8th — represents a perhaps once-in-a-lifetime opportunity to travel back in time and become a witness to history. Both Nas — whose debut LP, Illmatic, is commonly considered the best rap album of all time — and Lauryn Hill — whose only solo LP, The Miseducation of Lauryn Hill, was the first hip-hop project to win Album of the Year at the Grammy’s — are like walking relics from a former version of hip-hop, hardly recognizable against modern standards. But performing after Chappelle, who is himself also representative of a long-gone era, one in which impolite humor and cable television ruled supreme, the pair truly succeeded in establishing a sense of then.

Throughout his forty-five minute set, Chappelle appeared in full-form, talking through even the touchiest of subjects in his classically casual tone and unflinching against today’s heightened expectations for correctness. Skewering the famous sexual assault allegations against Michael Jackson, he minimized the late, great pop star into the “Jay-Z” of hanging with kids, drawing parallels between MJ’s odd indulgence in children’s fantasies (he owned a monkey, an amusement park and beds dedicated exclusively to jumping on) and the veteran Brooklyn rapper’s similar obsession with luxury goods (references to cars, yachts and watches decorate his every album). Traversing through race-relations, Chappelle laughed off the time that a pregnant Asian women (who is married to a Black man) became so offended by his commentary on interracial marriages that she went home to write a complaint to his promoter. And, finally, sweating through a bit that he swore he wouldn’t have told if attendees’s phones had not been locked into inaccessible pouches upon their arrival, Chappelle cringed at memories from a night of clubbing in Hollywood during which he danced (initially unbeknownst) with a transsexual woman.

Clearly, Dave Chappelle was simply being Dave Chappelle, but in 2017 that’s a major accomplishment in its own right. Throughout the next month, the PowerNomics Tour will bring him — along with two equally historic and fabled musicians — into fifteen more cities, fifteen more jam-packed theaters filled with thousands of people, old and young, who could’ve probably never predicted such an opportunity would arise. But more importantly, it will also generate millions of dollars worth of proceeds, a major portion of which its team has pledged to donate towards further enfranchisement of African-American communities.

This tour is not simply a parade of nostalgia for nostalgia’s sake, and it’s also not an attempt by old artists to collect new cash. Rather, it’s a strong-handed effort by a legendary team of Black entertainers to merge their platforms and heighten their impacts — both on the crowds they entertain and the communities that they will assist. This point was hinted at by a briefly serious Chappelle in the final moments of his set. Addressing Detroit, he professed how proud he is to be among residents of the largest Black community in American history, then reminded attendees that Motown — which was launched right here in our own backyard — is still the most quintessential example of a Black cultural enterprise, period.

“Detroit, I’m gon’ fuck with you until the wheels fall off!”

Just like that, it was time for Nas and Lauryn.