Jessica Winter writes on the seminal influence David Letterman had on her adolescence, something I concur with. In the mid-80s, Letterman was it:
To my suburban elementary-school self, David Letterman was a window into urban adult life. He was a figure both accessible and aspirational, crackling with frictions of personality: a Midwestern loner-type yet somehow the hippest guy in New York City; a guy beset by self-doubt and self-loathing yet confident enough to build a late-night institution around himself; a guy palpably uncomfortable around people who made a stratospheric living by talking to people; a guy with a pathological aversion to embarrassment who pursued embarrassment of himself and others as a vocation—maybe as a way of cauterizing a primal wound.
In high school, one of my best friends and I had a falling out for many months, over something unmemorable, the sort of falling out that was likely over something trivial, but that at the time seemed historic.
What mended our friendship was our mutual and independent discovery of David Letterman in 1985.
I had watched him since his short-lived morning show, and got a chance to be an audience member to his show in 1994 (with Woody Harrelson the main guest, promoting Natural Born Killers.)
You wouldn’t think it now, given how curmudgeonly, disagreeable and, well, just plain lazy (both comedically and politically) Dave has become in the past decade, but there was a time when what he did was… alive and new. He did adventurous remote segments with total strangers that were thrilling in their comedic spontaneity and immediacy.
His comedy style could be guerilla, before Sacha Baron Cohen, self-deprecating, transgressive… before being transgressive become… conformist, and emblematic of postmodern irony, before postmodern irony became tiresome 24/7 fair on Comedy Central.
While Letterman’s exit from the late night stage won’t be missed all that much with today’s demographics, his retirement signals the end of an era for late night television, as well as the fact that I’m getting old.