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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Released in 1965, Sammy Davis Jr.'s autobiography became an instant classic, one of the most dynamic celebrity memoirs ever published and a testament to Davis’s barrier-breaking success as a black man in America. But the story behind the book, which was conceived and developed by two white ghostwriters -- and the racial and sexual dynamics of Davis's life during the years leading up to its release, which included two marriages and one relationship with a white movie star which almost got him killed -- are even more fascinating.

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In the early 40s, both Dean and Sammy idolized Frank Sinatra. 20 years later, they became Sinatra’s cohorts in the Rat Pack, and, through Vegas gigs and increasingly disposable movies, the trio set a standard for grown men behaving badly that’s still influential today. In this episode, we’ll reveal what the Rat Pack’s Vegas shows were really like -- racist, homophobic, misogynist warts and all. We’ll also discuss the web of corruption linking these performers to the Mafia and the Kennedys, culminating in the death of an actress, and the death of the pretense that the Rat Pack racket was all innocent fun.

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After the breakup of Martin and Lewis, Dino has to figure out how to stand on his own as a solo act. He ends up developing an on-stage persona as a happy drunk, while at the same time, developing a resume as a serious actor in some of the biggest hits of the late 1950s, such as Some Came Running and Rio Bravo, through which he emerged as a kind of icon for the white masculinity crisis of the 1950s. How did Dino pull this off, and why was his interest in being taken seriously so apparently short-lived?

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Sammy tests the power of his new celebrity, on Broadway and in Hollywood, where he stars in the most controversial movie musical with an all-Black cast of all time -- a movie which is still being suppressed today.

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In the first half of the 1950s, Martin and Lewis mint money as movie stars--and find unique ways to make their access to gangsters payoff--but stardom tears them apart. During this period, Sammy tries to prove himself to a Hollywood that still has little use for Black performers. Then, a horrible accident changes Sammy’s life--and changes his perceived value to the gate-keepers of the entertainment industry.

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Dean Martin meets and begins collaborating with Jerry Lewis. Martin and Lewis — an Italian and a Jew — become the most successful nightclub act in the country, and transition to Hollywood. Meanwhile, Sammy Davis Jr, determined to get the attention of the white entertainment world, starts working impressions of white stars into his act.

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Sammy Davis Jr. and Dean Martin would become icons for how immigrants and people of color could access the American Dream in the 20th Century. Both grew up in marginalized communities where they learned an ethos of success based on hustle. Today we’ll track both Dean and Sammy to major coming-of-age moments in the middle of World War II. Coming up in industrial Ohio as both a card dealer and a nightclub singer, Dean learns how and why the house always wins. As a child, Sammy joins his father’s touring dance act, and eventually becomes the main attraction, before the war forces him to encounter racism at a level he’d never experienced before.

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When Hollywood mogul Walter Wanger (Jon Hamm) shot an agent he suspected was having an affair with his actress wife, Joan Bennett (Zooey Deschanel) — one of the key femme fatales of 1940s film noir — Bennett was the one who paid a public price for her husband’s crimes. Joan and Walter’s granddaughter/filmmaker Vanessa Hope, and film historian/podcaster Karina Longworth (You Must Remember This), tell the untold story of the Bennett/Wanger romance and professional partnership — a film noir played out in real life.

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The Hollywood studio system begins to crumble, and Louella and Hedda decline and fall, too. But just as a new generation of filmmakers rises from the ashes and reinvents the movie business, so too does gossip find new life in a new look. We’ll end our season by talking about a woman who was the antithesis of Louella and Hedda -- liberal, Jewish, sexually forward, and so unwilling to play the industry’s games that she may have ensured the death of the gossip columnist as star. 

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