David Letterman began his Late Night gig as a self-described “gap-toothed, unknown smart ass.” But thirty highly successful years later, Letterman’s comedy formula has evolved: he no longer attends all the meetings or makes all the decisions and stupid pet tricks are a thing of the past. Letterman began his television career as a weatherman, but moved rapidly up to anchorman and talk show host. He left for L.A. and, after only three years on the comedy scene there, he found himself guest-hosting the Tonight Show. He talks to Alec about how a quintuple by-pass and the birth of a child have dramatically shifted Letterman’s priorities. 

Michael Douglas has lived in the same apartment overlooking Central Park for decades. Alec joins him there for a compelling conversation about what makes a great director and why playing the villain is so wonderful. Douglas reveals how competition with his father, legendary actor Kirk Douglas, shaped both his career and his life as a parent. He says he’s much more honest with his young daughter than he ever thought he’d be. Douglas explains how his father’s early brush with death, and his own cancer diagnosis affected them each in different ways.