Rory Rosegarten started his career as a comedy manager by the time he was 20 with a whopper of a first client: the already legendary Robert Klein. More than four decades later, as founder and still president of The Conversation Company, Rosegarten manages a small but highly successful comedy clientele — his longtime roster includes both Brian Regan and Ray Romano, his newer client Tom Green recently premiered a documentary, a stand-up special and a docu-series all this year on Amazon Prime Video, and he’s currently working with comedian Gary Valentine on a TV series based on golfer John Daly. Rosegarten sat down with me over Zoom to talk about his teenage years interviewing celebrities first for his high-school and then for Playboy magazine, how he recruited other comics to work with a manager younger than them during the 1980s comedy boom, and how some things change and some things never do in the comedy business — including the fact that Rory has done it all while always living in Long Island. There’s a lot to get to, so let’s get to it!