Makaya McCraven takes his frequent-flyer status seriously. As a busy traveling musician, the drummer, composer, and bandleader regularly crosses oceans to perform, and he’s not about to risk losing sight of his or his bandmates’ gear. “Being in the early boarding group exponentially raises your chances that they’re not going to hassle you,” he says over Zoom from his Chicago home ahead of a lengthy fall tour. “That they’re not going to be like, ‘Sir, we have to take that guitar from you. We’re going to put it under the plane.’ And I’m like, ‘No, you’re not taking his guitar. You’re not taking my cymbals.’ So the status really comes in handy.”

It quickly becomes clear that, in laying out his approach to “playing the airline games,” the 39-year-old isn’t just making small talk. “I am a little obsessive about it,” he adds. “If you’re a person who travels a lot, if you give me the chance, I will lecture you, you know what I mean?”

McCraven brings that same laser-focused, deeply analytical spirit to just about any topic, whether he’s mulling his pre-tour domestic checklist (spending time with his two kids, testing his motion sensor and security system), tracing the evolution of his onstage attire (as “a performer who sweats a lot, like profusely,” he’s come to favor simple black T-shirts, accented with a striking necklace made from a circular cymbal fragment), or unpacking the unique blend of live improvisation and hip- hop-informed studio tinkering that’s helped make him one of the most talked-about jazz musicians of his generation.

Even the title of his new record, In These Times, comes packed with various meanings and inspirations. On one level, it nods to the long-running progressive Chicago magazine of the same name, where McCraven gave a candid interview in 2014 about the realities of life as a working musician, in the spirit of the publication’s late contributor Studs Terkel’s celebrated oral histories. On another, it highlights the variety of tricky time signatures McCraven employs within the compositions, informed by the Eastern-European folk music he’s played with his mother, the accomplished Hungarian singer Ágnes Zsigmondi.

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