Questlove and Black Thought on how quarantine unlocked their creativity

DJ sets, cooking shows, poetry readings: Sheltering in place has changed how The Roots and manager Shawn Gee think about how to engage audiences.

Questlove and Black Thought on how quarantine unlocked their creativity
[Photos: Bryan Bedder/Getty Images for Hulu (Questlove); Santiago Felipe/Getty Images (Black Thought); Eric Krull/Unsplash]

Ahmir “Questlove” Thompson and Tariq “Black Thought” Trotter of The Roots, along with their manager, Shawn Gee, can confirm that they fell into what two out of the three of them describe as a monotonous rut over the past few months pre-coronavirus.


They had a lot of ideas that they wanted to see come to fruition, but not enough time to create. They were so busy with other stuff—from their personal projects to their The Tonight Show Starring Jimmy Fallon gig to touring to planning the 2020 Roots Picnic—that some ideas had to be put on hold.

Trotter described it as a predictable daily schedule with a few periods where they could be creative, but with long periods of monotony as they played the waiting game.

Thompson cracked a joke about how they were the kings of seeing something, not liking it, and vowing to create something better, but never doing it.

Then, as for so many others, the pandemic upended everything.

For the past few weeks, they’ve had a lot more time to be more creative and we’re going on the fourth week of content coming from their Two One Five Entertainment wheelhouse (the Picnic has been postponed until August 1 pending what happens with the pandemic). So far, viewers have been treated to over 50 pieces of content such as live DJ sets from Questlove; Behind the Keys with James Poyser, where Poyser, The Roots keyboardist, shares the stories behind music he has made with the likes of Mariah Carey, Lauryn Hill, D’Angelo, and more; Streams of Thought With Black Thought, where he has discussions with other creatives and reads excerpts from things that inspire him or that he has written himself; Guitar Stories With Captain Kirk (The Roots guitarist); acquired content from friends like producer J Period; and more, all streamed across The Roots’ social media pages.

There’s a highly curated content schedule released on a weekly basis, and next up for May 1, is The Bridge: Conversations in the Diaspora, which is a chat with African creatives; the Questlove Supreme podcast, live with guest Ilana Glazer, as well as more live DJ sets from Questlove through the weekend.


The themes and conversations of what they’re making are constantly changing because the concepts are about more than just quarentainment.

This is about The Roots creating more music-related content that can be produced, marketed, and distributed on their own terms. It started last year, when Gee, Thompson, and Trotter founded their production company (Two One Five Entertainment) and sold a six part documentary series to AMC titled Hip-Hop: The Songs That Shook America, which aired last fall and received good reviews.

“Our fundamental mission with Two One Five is to be the global leader in compelling music storytelling,” Gee tells Fast Company. There are a lot of great directors and production companies that have told one-off stories, but we haven’t seen anyone become a hub for diverse, compelling, music-based stories. We will eventually spread our wings outside of music, but initially, the majority of our content will be music-focused because of our obvious connection.”

The collective is excited about the business they’re building, and there’s a lot to take in with multiple creatives streamlining several ideas. Here, the trio breaks down the process—and how their creative aspirations will transcend the COVID-19 crisis.

Shawn Gee’s Strategic Reaction

The first days of the COVID-19 crisis were full of anxiety for Gee. It was the usual stuff—processing what was happening with the world, and what it would be like to be hunkered down for an unknown amount of time. The first few days involved everyone in the circle making sure that everyone was okay, but after almost two weeks in, it was clear that there was no end in sight.

Then the quarantainment started.


Most notably, D-Nice started #ClubQuarantine, a live DJ set that became the virtual place to be. By that point, Gee, Trotter, and Thompson, who loves to DJ anyway, began to set their master plan in motion.

“This was a reaction. Prior to this, I always stayed three to six months ahead of the guys as far as strategy and what I’m executing. They still had The Tonight Show, which they still have, and shows that I had set up three or six months prior, but this situation was a reaction,” says Gee. “We were already moving in that direction from a content production perspective, and this gave us the opportunity to incubate something and really build something that we feel is going to live well beyond this COVID time period.”

The creativity blitz kicked off with Questlove providing a “90s slow jams” set designed as an after-party to #ClubQuarantine, as well as a fundraiser for Food Bank for New York City. There’s always a charity element involved, because that’s a no-brainer.

“Ahmir loves to DJ, so once we saw some DJ’s going live on a nightly basis, we quickly put a strategy in place for Ahmir to do what he loves,” says Gee. “However, instead of just DJing on IG—like everyone else was doing—I asked if it was possible to do both on IG and YouTube, because although IG has the audience, with YouTube, at least there is a path to monetization. We already had a YouTube channel setup for The Roots and a rev-share deal in place.”

Bryan Calhoun, leader of their tech team, added on to the streaming idea. He figured out how to make possible simultaneous streaming across Twitch, Facebook, Periscope, YouTube, Instagram, and Facebook, and that’s how #QuestosWreckaStow kicked everything off.

How Your Favorite Music Teacher Found His Groove

Questlove’s #ClubQuarantine after party was almost going to be a comical situation, with Questlove playing bad cover-band versions of songs—similar to the “Do Not Play” segment on The Tonight Show—because the point was to make it authentic. However, Gee convinced him that he could make it authentic by owning his role as the musicologist people needed to help keep their minds off real-life drama.


“Once Oprah is in your party, like with DNice, then it’s like, okay, you’re clearly going to be America’s—or the World’s—Coronavirus DJ. And I don’t want to be Scottie Pippen to his Jordan at that moment,” says Questlove. “My whole narrative is that I’m this musical griot or this musical expert with 170,000 pieces of vinyl that you can Google, but now that I’m thrown in the pool, I realized, yeah, I have 170,000 records, but at the end of the day, I know maybe 400.”

Questlove has digital access to about 30% of that massive collection and decided to get to know more of his songs in front of a live audience. It’s different when that audience is the internet, but Questlove gets it now. He can reach more people. He’s having fun with his selections, and his diverse and meticulous approach to music shows up in his nightly playlists.

“I challenged myself to do a dancehall set that didn’t require me to play ‘Murder She Wrote.’ I’m gonna try and do the salsa set that doesn’t require me to play like ‘Suavemente,’ all the Captain Obvious stuff,” he explains. “So, I mean just as a music lover and a musician, it’s challenging me to find exciting ways to present music.”

There was a Prince tribute, a Bill Withers tribute, a night of all Brazilian music, a relaxation set, a dancehall set, and it’s constantly changing. Listeners get treated to music they might not be familiar with, studio session stories, music history lessons (he’s making one of those lessons, about the Harlem Cultural Festival, which took place at the same time as Woodstock, into a documentary), and music-theory breakdowns, like how E major is a popular key in pop music.

“On average, I’m somewhere between 10,000 and 20,000 people, depending on your willingness to put up with why this snare is more important than this particular microphone technique or something like that,” says Questlove. “But what I’d slowly realized by day seven is that I don’t even consider this the new normal. I just consider this what I’ve been preparing for all my life.”

Black Thought’s Freestyle Culinary Stylings

Before coronavirus, Black Thought was working on Black No More. It’s a Broadway play that he wrote and produced with Academy Award-winning writer John Ridley (Twelve Years a Slave). The initial plan was for it to debut at the end of the year, but now it’s most likely going to premiere in early 2021.


In the meantime, Black Thought has been sharing excerpts from it as part of his creativity series. Black Thought is chill about it, but Questlove describes it as what could potentially become his MacArthur Genius moment adding, “If y’all thought that freestyle was brilliant, wait until y’all see this play.”

The play is an adaptation of George S. Schuyler’s Afrofuturist Harlem Renaissance-era novel, where a man promotes a machine that promises to remove the burden of race from any person of color by turning them white. In addition to the play, Black Thought has also been reading poems that he wrote that were supposed to be on an EP, passages from books, and generally sharing things that inspire him—in addition to hosting conversations with the artists Carrie Mae Weems and Bisa Butler, raptivist Mysonne, and more.

It’s the type of discourse and presentation you’d expect from a man with “Thought” in his name.

But the man—who has been regarded as one of the greatest lyricists of all time—says that he cooks as well as he raps, and we’re about to witness the culinary content he’s preparing. It’s set to launch over the next couple of weeks.

“What did Liam Neeson say? I have a certain set of skills. Cooking is also part of my skill set. It’s the way in which I express love,” says Trotter. “I’ve always been the person who cooks for the holidays, and I’ll cook for 25 or 55 people at a time. I do the big meals with the barbecue grills and all that sort of stuff has always been my deal. Back in the day, we used to host a brunch, or breakfast, lunch, dinner sort of thing that we would have weekly in the early 90s at my apartment in Philly, and I’ve continued that tradition.”

Black Thought says he doesn’t write a lot of his recipes down, much like his freestyles, but in his lifetime before entertainment he worked at multiple restaurants and picked up techniques from his grandmother. The only recipe he has ever written down was for a cioppino published in Questlove’s cookbook, Mixtape Potluck, which came out last October.


“Anyone who knows Questlove knows him as a culinary ambassador but what people don’t know is—and he has been more vocal about this in recent years—is that his entree into that world was me,” Black Thought says. “I’m not formally trained, but I’ve always fancied myself a foodie and I’ve always been a chef. I’ve always wanted to do a cooking show, so we’ll see where this goes.”