Questlove is known for making playlists for his friends. His friends, as O’Brien put it, just so happen to be “some of the most famous people in the world.” Questlove said the hobby “started with The Obamas” and admitted to some slight trolling after O’Brien asked, “Do you ever throw something in there — like the theme from Gilligan’s Island — just something that’s gonna freak [former US President Barack Obama] out?”
“I do that all the time,” Questlove said. “He doesn’t question much. There’s a few people who are like, ‘Did you really mean to put this version of that song on there?’ I will lightly troll. I’m not trying to troll more than I’m just trying to expand the palette.”
The Roots legend continued, “Because, I think, oftentimes when it comes to streaming, there are billions of songs out there, but we’re only gonna go to the 32 songs that we know. And I’m willing to do the musical, metaphorical equivalent of the Shawshank sh*t crawl. I go through about 500 songs a week, of which maybe seven are cool.”
Questlove then explained his Blue Ivy-related reasoning behind adding Beyoncé and Jay-Z to the group — even though it seems to me that the only reason he’d need is that they are, ahem, BEYONCÉ AND JAY-Z — and shared that Bill Hader, Spike Lee, Martha Stewart, Kenan Thompson, and Norah Jones are also among recipients of curated Questlove playlists.
“I text 700 times a month to [this] list of people,” Questlove said, handing his phone to a very impressed O’Brien. He asked O’Brien if he’d want to be added to the list, which feels like a rhetorical question.
Watch the clip above.