This episode was originally released on December 14, 2021. Listen to help prep for the next episode of our new season, The Old Man is Still Alive.

In the mid-1960s, 47 year-old Dean Martin proves he's still got it by knocking the Beatles off the top of the pop charts, and by launching his long-running TV show, which brought a version of his nightclub act into America’s living rooms every week. But his middle-aged drunk schtick sours as the decade of hippies and Vietnam wears on. Sammy Davis Jr has his own challenges, living up to the expectations of a new generation of activists--and he only makes matters worse by embracing Richard Nixon. After disastrously dabbling with Motown, Sammy records “The Candy Man” -- a silly novelty single that he hated, but which ended up saving his career.

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Flashback: Sammy and Dino — Generation Gap 01:26:56 Share

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Flashback: Sammy and Dino — Generation Gap