Q&A: Questlove on Philly’s music, food, and the El

Keep your eyes peeled if you’re riding the El this winter. You might run into a hometown hero.

When Questlove’s feeling homesick, he’ll throw a hoodie and shades on and ride his favorite form of SEPTA, the Market-Frankford El. It’s kind of like when Beyoncé goes to Target — just Philly style.

The drummer, DJ, filmmaker, and artist divulged this nugget during an interview in his trailer as day one of the Roots Picnic — which he executive produced and also performs at — unfolds around him. He’s reclined in a tan leather seat wearing a flannel shirt and gray Pollex clog by Salehe Bembury Crocs as a stylist twists his hair.

About an hour earlier, he raised a can of Stella Artois to a small group of select VIPs and sweepstakes winners as part of the beer company’s partnership with him. The result was Questlove’s Cheesesteak Diner, a red-and-white checkered pop-up diner in a wooded area hidden away from the rest of the festival.

It was part of a partnership with the beer company for its “Let’s do Dinner” summer series, featuring pop-up food installations in Philly, Los Angeles, Atlanta, Chicago, and New York. Each pop-up features different artists and themes.

The theme for Philly’s was natural: Questlove has been an investor with plant-based Impossible Food Inc. since 2017 and first launched his cheesesteaks about two years later, a sustainable tribute to his hometown. The menu also featured a kale slaw and lemon pepper popcorn, a nod to the artist’s 2018 popcorn seasoning collab with Williams Sonoma.

“I had to tell [Williams Sonoma] that lemon pepper is the new barbecue,” he said.

The artist’s relationship with food is long-spanning. It’s what he says contributed to The Roots’ success — food-boosted jam sessions that sparked the local scene’s neo-soul movement. And his reputation for throwing a solid party reaches back even further.

» READ MORE: Review: Jill Scott shines on Day 1 of a sold-out Roots Picnic in a glorious day in Fairmount Park

We talked about the Roots Picnic legacy, Philly’s ever-evolving food and music scene, how he manages his time, and of course, game night.

This interview has been lightly edited for length and clarity.

So two years ago, I finally had to give in. Artists are sort of leery about seeming too “businesslike.” There’s this perception that artists are artists and business is business. During the period when I entered the movie world, I was dropping too many balls. My manager was like, “You’ve got to step it up and get a chief of staff.”

The chief of staff is the person who manages my seven managers — a DJ manager, a Roots manager, a Tonight Show manager, book manager, food manager. Once you get a chief of staff, she gets everyone to stick to a schedule.

Because it’s a lot. Post-Oscar, the world’s my oyster now as far as the film world, there’s also a Roots record, and plays I’m working on. I’m able to wrestle these eight or nine things, but also sleep for eight hours, implement date night, and have a personal life, exercise, meditate and stuff. You have to be Zen in order to do this.

We’re trying to figure out what our endgame is. It’s to be determined. There’s a future venture coming up in about a year. I’ve been kind of in movie and book mode right now. Food mode will eventually catch up and we’ll announce in about a year.

The key to life is to be very careful with what you ask for. You have to be prepared.

What’s hilarious is my manager was ecstatically losing his mind over the fact that this year will probably be our heaviest population. Two days, 65,000 people. He said, “Man, not bad for some guys whose first festival was just 3,700 people.”

There was never a moment where I took notice that “Oh, now The Roots can sell out Radio City Music Hall.” I think my mind was just so used to us playing venues for 1,000 people. So to go from that to this, it’s almost like too much. I don’t even think The Roots themselves could headline this venue on our own.

In ‘93 there was basically just Lollapalooza, only a few festivals. We played one of the first Coachellas. Europe has over 7,000 festivals. We wanted to bring that back home. That was our dream and here we are living it.

Returning from that time we lived in London, we knew that whatever we learned over there, we were going to bring here. The one thing that always happens in London is jam sessions. Back home it was like “Who are we going to convince to work on our album and do jam sessions?” Our manager got Chef Terry from Zanzibar Blue [known as Philly’s “Premier Jazz Club” from 1990-2007 and owned by the Bynum brothers]. Every creative is suddenly migrating over.

Those first four years I think spawned 14 record deals, for Musiq Soulchild, Jill Scott, Common, a 10-year-old Jazmine Sullivan. Artists from all over began choosing Philly because they heard something was happening here. My manager was like, ‘We just have to create a scene, and we’ll do it with food.’ Now, it’s in reverse. Back in the ‘90s, we used food to entice the music community. Now, I use musicality to entice people to eat. So when I throw my food salons or game nights, it’s the opposite. I’m not going for the jam session, it’s for the social gatherings.

The magic that makes it work, I know that perception might seem like only a certain type of person gets in, but every gathering I have has — from college students to, yes, a certain popular singer [he’s talking about fellow Pennsylvanian Taylor Swift for those uninitiated]. And it’s not even by design. It’s so normal.

The word guests used at first, I was cringing, was wholesome. One time we had a high-caliber artist come to our L.A. one. I didn’t know what the protocol was. They were sending security detail. And after like 20 minutes, the person was like, “Wait, you guys are really just playing games here?” And I was like, “Yeah, what did you expect?”

It makes people drop their guard and the whole reason I do it is for the next night. No one knows this artist and this director linked up and now they’re working on a project together. I really just want my worlds to collide and for people to make friends. Even said popular singer came into zero fanfare. It was more like, “Of course you’re here — you’re gonna draw [an Uno card].”

My all-time favorite thing to do is travel, so I know that sounds weird, but I’ll drive to Philly, usually in the winter so I can wear a hoodie and no one sees me. I love public transportation, it’s an anticlimactic answer. But if I didn’t have Lil Wayne rehearsals tomorrow I’d probably be on the El. I wanna do a complete round trip of it. I look so nondescript. You can’t come with fanfare or security. I blend in, put a hat on, glasses, because the first thought is always “no way that’s him.” Front train, no one can see my face.

It’s everywhere. During the pandemic, I would go on YouTube and watch first-person videos from the front car. I love that so much. Back to careful with what you wish for, I always joked that in my 15 years living in New York City, I’ve yet to see a train show [where performers take over a car]. Sure enough, two weeks ago I overslept for something I had to do with [Jimmy] Fallon. So I get on the train, first car, and there’s a dance troupe. I did it!