Lewis On The 500 with Josh Adam Meyers

"It meant a lot to me to be able to talk about a life changing album with Josh Adam Meyers who knows way more than I do about music." - Lewis

Album #97 | Bob Dylan - The Freewheelin' Bob Dylan | Lewis Black (July 29, 2026)

Legendary stand-up comedian and political satirist Lewis Black joins The 500 with Josh Adam Meyers for a monumental, deeply passionate episode. In this session, they dissect the unmatched cultural explosion of The Freewheelin' Bob Dylan (1963). Shifting completely away from standard folk norms, this record established Dylan as the ultimate voice of a generation fighting a broken status quo.Lewis Black unleashes his trademark therapeutic rage and sharp wit to match the biting prose of early Dylan. Together with Josh, they break down the album’s heavy civil rights anthems, the bitter truths of 1960s war politics, and how a lone kid with an acoustic guitar and a harmonica single-handedly rewrote the rulebook for modern American songwriting.