David Letterman’s telephone routines are, in my opinion, among the funniest bits he ever did in his 32 years as a late night television host. He called New York City payphones and engaged whoever answered in some sort of chit-chat, but he also called people he could see sitting at their desks in office buildings, his mom, wrong numbers, the Butterball Turkey Hotline, and so on. I don’t know how authentic or unscripted a lot of these calls really were but there was always something tantalizingly random about the connections.

This encounter is not quite as electric as others that I remember but it has its charm, and seems to have captured a genuine passer-by in full candor.

I don’t know when Dave stopped calling payphones but I got a distinct impression at some point that word had been getting out about which payphones he was going to call and at what time. Actors and wannabes glommed on to this and camped out at the payphone, waiting to be hilarious. I don’t have any evidence to back up that claim but at a certain point the spontaneity of these calls seemed to evaporate.

As Dave mentions in this skit, Times Square appears to transform itself any time you blink your eyes. The TKTS booth is still present but overall Fr. Duffy Square looks nothing like it did in May, 1992, when this segment aired. The cluster of three payphones is no longer present. Even if they were it is unlikely they would accept incoming calls as they did back then. The “New York Telephone” brand can still be seen on a small number of payphone enclosures, while the now-poignant “110 stories and just as many entrees” sign advertising Windows On The World cannot.

My favorite line from this bit is near the end. Dave asks the man to look up at the Jumbotron and tell him what he sees. The man says “I see David Letterman,” to which Dave responds “There’s been a terrible mistake”, since the gentleman should be seeing himself — this as a couple of observers videobomb the proceedings.

Thanks to YouTube user antisepticmanor for posting this and other vintage Letterman bits from the early 1990s.