Malcolm Gladwell is known for taking ideas that seem too big to properly understand—massive societal change, uncanny expertise, the mysteries of memory—and methodically bringing them down to earth. For instance, in his 2008 book Outliers, he explains the Beatles phenomenon as a simple result of practice, stamina, and repetition: By the time John, Paul, George, and Ringo broke through in 1964, he writes, the quartet had played around 1,200 shows, making them unusually primed for pop dominance. To read Gladwell’s work is to enjoy an endless series of these kinds of eureka moments.

At 55, he’s an award-winning author, a podcast mogul, and, more quietly, one of the best music writers alive. The most recent episode of his Revisionist History podcast, “Analysis, Parapraxis, Elvis,” investigates why Elvis Presley always screwed up the exact same part of “Are You Lonesome Tonight?” during live performances and features a surprise cameo by Jack White; it’s one of the most enlightening pieces of music criticism I took in all year. Gladwell’s newest podcast, Broken Record, takes his love of music one step further.

The series finds him working with producer Rick Rubin and journalist Bruce Headlam as it aims to add in-depth insight to our modern world of passive streaming. So far, Broken Record has featured conversations with Nile Rodgers and Rosanne Cash, and an upcoming episode will have Gladwell and Rubin discussing the late Tom Petty’s Rubin-produced 1994 album Wildflowers. With the famed thinker indulging his inner music fan like never before, we spoke with him about the songs that have flipped his mental light switch across his 55 years.