Questlove has a unique hobby of curating playlists for his circle of friends, and his friends just happen to be some of the most famous individuals globally. The journey of creating playlists for his friends began with none other than the Obamas. During a conversation with Conan O’Brien, Questlove admitted to some light-hearted trolling in his playlist-making adventures, prompting O’Brien to inquire if he ever added surprises like the “Gilligan’s Island” theme to throw former US President Barack Obama off balance.
Questlove chuckled and confessed, “I do that all the time. He doesn’t question much. There are 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 music icon elaborated on his approach, emphasizing the importance of exploring beyond the familiar hits. He shared, “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 also revealed his rationale for adding Beyoncé and Jay-Z to his group of playlist recipients. However, he noted that their status alone should suffice as a reason. Yet, he extended his music curation to include notable names like Bill Hader, Spike Lee, Martha Stewart, Kenan Thompson, and Norah Jones.
“I text 700 times a month to [this] list of people,” Questlove mentioned, showcasing his dedication. He even handed his phone to Conan O’Brien and asked if O’Brien would like to be added to the list, a question that seemed more rhetorical than anything else.
Questlove’s playlist-making hobby has indeed reached an impressive level of celebrity involvement, offering a unique glimpse into his musical passions and the joy he derives from sharing them with his renowned friends.