When acclaimed pianist and composer Robert Glasper began amassing recordings from his now five-years-strong “Robtober” residency at New York City’s famed Blue Note jazz club, there was no plan beyond keeping a record of the magic that’s sure to unfold whenever Glasper’s friends and collaborators join him onstage. Had he been more prescient about curating a selection of these performances for a project like Keys to the City Volume One, he might have realized the treasure trove of material he was sitting on. “It’s like five years [of recordings],” he tells Apple Music. “You got to think, it’s two sets each night for a whole month. And when I first started, I only had one day off, so I was doing six days a week the first few years. And so many people come in. I looked up the scheduling of who I had on the bill that the audience knew of—that’s one thing—but there were so many people that just popped up on us. So many of those kinds of moments.” In the end, Glasper chose nine standouts. The set list runs the gamut of what audiences might encounter on a given night, with Glasper having selected performances of songs you’re unlikely to hear elsewhere. They include versions of The Roots’ “Step Into the Realm” featuring Black Thought, Outkast’s “Prototype” as sung by Norah Jones, a cover of Chick Corea’s “Paint the World” featuring Thundercat, a particularly dialed-in arrangement of Glasper’s early-career Mulgrew Miller tribute “One for Grew,” and an impossibly groovy revamp of Ready for the World’s “Love You Down” sung by the voice we hear on all three of Glasper’s 2024 Apple Music collaborative projects, Meshell Ndegeocello. “She’s an icon,” Glasper says. “And just one of the greatest artists, in my opinion, ever. I don’t think she gets as much flowers as she should.” Keys to the City’s sole original composition, “Didn’t Find Nothing in My Blues Song Blues,” features improvised singing from Esperanza Spalding, and plays—with its lighthearted onstage banter and meandering storyline—as something Glasper says is exemplary of the Robtober vibe. “[It] shows the other side of us—the pure, unadulterated—just two personalities with their instruments, jazz cats,” he says. “It felt so cool, so natural. She was just like, ‘Hey, you want to do a blues?’ I was like, ‘Cool,’ and then we just started. We never rehearsed it. She didn’t know what she was going to say. That’s why I called it what she said, ‘Couldn’t Find Nothing in My Blues,’ because it was literally made up in the moment. Those are cool things, because it takes courage to put shit out that you didn’t plan.”