Questlove on the benefits of collaboration

In his new book, Creative Quest, the Roots frontman explores how creative differences can lead to dream teams

Questlove hero image
Image Credit: Michael Baca

No one in music may be as fascinated with the art of collaboration than Ahmir “Questlove” Thompson, the drummer of hip-hop band the Roots. His new book Creative Quest, released in April by HarperCollins, is a guide to the creative process from start to finish that draws from his personal experience. It also doubles as his latest attempt to share what he has learned about working with others throughout his career.

Toward the start of his career, Questlove was part of the Soulquarians, a music collective that answered to music’s digital bent with analog sensibilities. Albums like D’Angelo’s Brown Sugar, Erykah Badu’s Mama’s Gun, and the Roots’ own Things Fall Apart resulted from the Soulquarians’ brief but fruitful existence from 1996 to 2002, epitomizing the height of neo-soul.

That period also became the seed for a running theory Questlove had for decades: There are two types of artists, the more commercially driven “achievers” and the more high-minded “creatives.” Working with the Soulquarians convinced Questlove that creatives worked best among themselves.

But Questlove doesn’t believe that anymore, not when the Roots have since worked with “achievers” like Jay Z, Usher, and Jimmy Fallon, to more success than he could have imagined. In Creative Quest, Questlove updates his terminology, rendering achievers “Type As” and creatives “Type Bs,” to better reflect how no one type is more inventive than the other. In fact, he stresses, the two can often learn from each other. Here are some examples from the book on what Questlove considers some of the most unlikely, yet most successful, collaborations in his career.


Jay Z’s tip for improving team collaboration: Be straightforward

In 2001, Jay Z approached the Roots to be his backing band for a landmark hip-hop episode of MTV Unplugged. But Jay’s musical persona as “the CEO as top-dog hustler,” and his shameless chase for commercial hits, made Questlove feel uneasy.

Questlove fondly remembers how, in the spirit of efficiency, Jay Z would simply ask: How would you make this better?

It turns out Jay Z is the easiest artist Questlove has ever worked with. Perhaps to fans’ surprise, Creative Quest reveals that the Soulquarians era had been a complicated guessing game. Questlove had to constantly figure out what type of feedback his fellow artists wanted to hear. In the book, he describes it as a “strange mix of ego jousting and creative strategy.”

But Questlove fondly remembers how, in the spirit of efficiency, Jay Z would simply ask: How would you make this better? “When you told him,” Questlove writes, “he’d take a little time to think about it, after which he’d either agree or tell you plainly why he wasn’t comfortable with that approach.”

This process worked so well, Jay Z wound up hiring Questlove as creative director for his 2003 Madison Square Garden concert—the basis of his Fade to Black documentary. He even signed the Roots to Def Jam Recordings when he was label president.


Usher’s advice on effective teamwork: Build off each other’s strengths

The Roots Picnic, the band’s music festival in Philadelphia, ends with a two-hour set where the Roots back the headliner. For its ninth year in 2016, the group performed with a classic “Type A” in R&B and pop. “Usher had a reputation as a guy who was more like Jay: a hitmaker, a chart dominator, a commercial presence who wasn’t as connected to the art on a deep level like, let’s say, the Soulquarians,” Questlove writes in Creative Quest.

“Maybe the more arty you are, the more you need to yin-yang it with an achiever: it produces results and reduces anxiety.”

Questlove learned from Usher’s total willingness to experiment, how he never said “no” once. “Maybe the more arty you are, the more you need to yin-yang it with an achiever: it produces results and reduces anxiety,” Questlove writes.

The Roots wound up rearranging Usher’s biggest hits to sound like older soul classics, relying on Questlove’s encyclopedic knowledge of the genre (his father was the late doo-wop singer Lee Andrews). By adding grit to Usher’s slick and sexy stage presence, the Roots drew deserved attention to his remarkable voice.

Again, good things come to those who collaborate: Last year on Questlove’s Pandora radio show Questlove Supreme, Usher proposed that he and the Roots do an entire album together.


A lesson from Jimmy Fallon on creative collaboration: Embrace constraints

When Jimmy Fallon asked the Roots to be his Late Night house band, the group was entering its 15th year as a freewheeling touring act. They had pursued critical acclaim over easy chart hits; albums like Game Theory and Rising Down made heady and cerebral statements about hip-hop and the world at large.

“There’s no less creativity than there is in a freeform Roots recording session … But in a TV studio, with a clock hanging over our heads, we are forced to distill and discipline our creative impulses.”

Now with The Tonight Show Starring Jimmy Fallon, as part of TV’s most formidable franchise, the Roots produce a tremendous amount of work in a short period of time. Live shows are taped each day at the studio at 30 Rockefeller Center promptly from noon to 7 p.m. Throughout that time, the band brainstorms and rehearses comedy bits, classroom instruments performances, and each guest’s walkover music. With this steady focus on delivering different musical outputs at a rapid pace, the Roots have become what Questlove used to call “achievers.”

And much to Questlove’s surprise, the group clearly finds this process rewarding. Next year will be its 10th season with Fallon, with Questlove serving as The Tonight Show‘s musical director.

“There’s no less creativity than in a freeform Roots recording session,” he remarks in Creative Quest. “There’s the same amount. But in a TV studio, with a clock hanging over our head, we are forced to distill and discipline our creative impulses.”

Creative Quest challenges readers to similarly reconsider who they believe would make a good team fit. If Questlove hadn’t been open-minded, had he stuck to his old theory that different creative types couldn’t possibly work together, then his own rise to cultural prominence wouldn’t have turned out as delightfully unexpectedly.


Christina Lee spent the night of senior prom trying to find the Roots’ Phrenology at her local Walmart.

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