Season Four of You Dig? launches with one of the most extraordinary trumpet players of our time: the legendary Wayne Bergeron.

Wayne sits down with Steve Wiest for a hilarious, wide-ranging musician-to-musician conversation about a lifetime spent making music at the highest level—and the remarkable people and stories he encountered along the way.

Wayne remembers his dear friend Jack Sheldon, including the unforgettable experience of playing “Taps” at Jack’s funeral on Jack’s own trumpet. He reveals a previously unheard Jack Sheldon project, tells the complete story of the infamous $100 piccolo trumpet, and takes us inside his experience recording Steven Spielberg’s West Side Story.

That leads to encounters with Barack and Michelle Obama, John Williams, Gustavo Dudamel, Steven Spielberg—and an absolutely unforgettable moment with ...