On reminiscing about their years about Emerson; on his early years in Burlington, MA ; on his childhood and making his friends laugh; on whether or not you can teach someone to be funny; on his nerves when he first started doing stand-up; on the challenges of starting out in stand-up comedy; on the Boston comedy scene compared to other cities; on his first time performing -- at The Comedy Connection: on classes and writing he did at Emerson
On his first stand-up performance (contd.) and on other comics he observed when he was first starting out; on the first joke he ever performed and on unknowingly learning techniques by listening to comedy performances on the radio; on every comedian being a teacher and a student at the same time; on starting to tell jokes with longer setups, on pauses in delivery, and on waiting out a laugh
On a comedian's relationship with the audience; on his love of words when he was young; on his advice to anyone with a goal - take the risk; on creative people attending Emerson University, and there being a dividing line in his life from before he lived in Boston and attended Emerson to after; on looking back at their time at Emerson; on Monty Python and on big events in 1969
On his comedy career really taking off at the Ding Ho comedy club; on his contemporaries who performed at the Ding Ho comedy club: on additional Boston-area clubs where he performed when he started out; on first watching The Tonight Show Starring Johnny Carson with his older brother (who loved Johnny Carson), and then wanting to become a comedian
On the four things he would't talk about in his act and his rules for performing -- and when/why he would break his own rules; on whether or not he's enjoying himself on stage; on how his first time on The Tonight Show Starring Johnny Carson came about; on his first, second, and additional performances on the show
On how he creates his material; on his first comedy album, "I Have a Pony," on his first HBO special, and on being nominated for a Grammy; on making a half-hour film, The Appointments of Dennis Jennings, and winning an Oscar for the film; on creating the film One Soldier; on his thoughts on social media and the internet; on whether or not he'd like to do a Netflix comedy special
On making creative decisions; on testing out material in theaters; on his film work -- Reservoir Dogs, Coffee and Cigarettes and Desperately Seeking Susan; on his guest appearances on Mad About You and The Larry Sanders Show; on advice to aspiring comedians and whether it was all worth it