Since a young age I’ve loved listening to comedians not just in their acts but talking about life. They’re individuals who have made a life off of continuous observations of people and places around them and tend to have a deep insight on the nuances of the world. Each of these interviews are about 15-25 minutes long and highly entertaining as Jerry Seinfeld condenses a day spent with comedic entertainers into the pivotal moments they share together.
Especially good episodes are
Alec Baldwin and his take on laziness.
Howard Stern (a personal favorite)
Louis C. K. Talks parenting
Trevor Noah and his first view of comedy between races
Sarah silvermen speaking of a life being raised without a filter.