Our summer tradition at Here’s the Thing continues, as staff members choose their favorite conversations from the archives for our Summer Staff Pick series. This week, we revisit Alec’s conversation with David Letterman, who began his Late Night gig as a self-described “gap-toothed, unknown smart ass.” Three decades later, Letterman reflects on how his comedy evolved, why he no longer makes every decision behind the scenes, and life after “stupid pet tricks.” He shares with Alec his path from weatherman to talk show host to guest-host of The Tonight Show—and how both a quintuple bypass and the birth of his son shifted his priorities.