Alec talks with late-night legend David Letterman. Letterman describes his early days as a local TV host in Indiana, followed by time working the comedy clubs in LA. In just three years, he found himself appearing on The Tonight Show; as Letterman says, "that's not supposed to happen." Baldwin also visits Michael Douglas at his New York apartment for a conversation about what makes a great director, a smart producer, and why playing the villain is the much more satisfying part.
Alec goes backstage with comic actor Chris Rock after a matinee of The Motherf-er With The Hat to hear what it was like for Rock to be in his first play. NOTE: Please Read the Content Advisory to the right. Alec also talks with Herb Alpert, legendary trumpeter and music producer. In 1966, Alpert’s band The Tijuana Brass sold over 13 million records, outselling The Beatles
Alec visits Lorne Michaels in his office at Rockefeller Center – the same office he’s had since 1975, when he created Saturday Night Live. Michaels and Alec talk about what led to SNL, and Michaels early years doing subversive political satire on Canadian radio. Alec also talks with writer Erica Jong and her daughter Molly Jong-Fast as they spar about sex and the legacy of the feminist movement.
Alec talks with Kristen Wiig – a breakout Saturday Night Live cast member who says she loves performing, but admits there’s also a “big part of me that’s just like: don’t look at me.” Alec visits talk show legend Dick Cavett at his home in Montauk, Long Island. Over iced tea, Cavett shares memories from five decades in entertainment.