The Michael Jackson Deep Dive

The Michael Jackson Deep Dive

April 17, 2026 · 1h 29m · Episode 305

About this episode

Dave and Milt explore the music and impact of Michael Jackson in a deep dive episode.

Dave and Milt crack open a special Past Tens where the subject is none other than the human moonwalk, Michael Jackson—timed nicely with the looming biopic that’s about to remind everyone just how absurdly dominant this guy was. We’re talking voice, moves, mystique, and that little side project with Quincy Jones that somehow turned into the most unfair three-album heater in pop history. Ground rules: solo MJ only. Sorry, Jackson 5—you’ll always have “ABC,” but you’re sitting this one out. From there, it’s ten categories and approximately 47 friendly arguments. “Most Well-Known Song” turns into a heavyweight bout—“Billie Jean” vs. “Thriller”—with no judges and plenty of yelling. “Where It Began” gives us the early runway (“Rockin’ Robin,” “Don’t Stop ’Til You Get Enough”), while “Mountain Moment” is basically the peak of the peak (“Beat It,” complete with Eddie Van Halen shredding like he wandered in from another genre, and “Wanna Be Startin’ Somethin’” doing…whatever that song does, which is everything). We dig for “Deep Cuts” (including a sneaky collab with Lenny Kravitz and a Wiz-adjacent pull), hit the “Chill Moments” (cue gospel chills and emotional uppercuts), and try to pick…

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Hosts: Dave, Milt

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