My Late Night With David Letterman Tapes

Revisiting our favorite music performances from the show for its 40th Anniversary

Late Night With David Letterman series premiere ad (Image: Pinterest)

The motor on my desk top dual audio cassette broke. I abused it making a movie. My last functioning audio cassette player was from BJs, a cheap, cute boombox with a great tuner and a DVD. Its sound killed, almost literally when I first played NRBQ’s cover of “Tonight You Belong to Me.”

I don’t know which supplier I was on the phone with about the boombox, maybe Samsung, but they warned me off multi-tasking electronics. They were quickly proven correct. The cassette player on the box quickly got worn out for the same problem as the dual deck. So, I told a friend to gift me an audio cassette to digital converter. Having this work sent out would have cost 100,000 percent more. But when the converter came, it didn’t work as advertised in Hammacher-Schlemmer’s catalogue. Rather than pay ransom for the whole collection, I’d have to prioritize the ransom I’d pay cassette by cassette until I find a good converter. But one cassette will never leave my hands. I call it Late Night Live… where the streets are dusty, the rivers are gusty and the people are trustee. This is the live music from NBC’s Late Night With David Letterman as performed on stage. Tonight, we have Harvey Pekar, The Late Night Librarian with Gus driving the bookmobile, and, Stupid Human Tricks. Now, here’s the man who would have led Indiana to a state basketball championship had he known not to kick the ball, David Letterman!

Instead, I have a Maxell XLII 60-minute cassette that used to start with Debbie Gibson lilting her way through the scales during the show’s introduction. The sound was crisp! But I have no way to listen without paying for professional conversion and it sucks because I taped them fair and square on a Super VHS from the previous night’s WNBC telecast while hanging with my girlfriend before we went to bed. Labeled on the cassette but without my recollection of their performances despite listening to this tape 1,000,000 times are Joe Cocker, Indigo Girls, Aaron Neville, 10,000 Maniacs and Run DMC.


VIDEO: 10,000 Maniacs perform “Don’t Talk” on Letterman 1987

One song I indelibly remember is from the Soup Dragons. They started “I’m Free” in command form: “Don’t be afraid of your freedom.” I don’t remember what George Clinton played, but Letterman reached out to him, “Don’t hurt anyone!” Clinton jumped into the audience and whipped up a dance party, dragging people right in front of “Dave’s” desk. Having worked at ABC, I’ll bet NBC people were pissed.

Spin Doctors did “Little Miss Can’t Be Wrong.” They played on the street near NYU. Blues Traveler did “Runaround,” Lisa Stansfield did “Been Around the World,” They Might Be Giants did “Your Racist Friend.” The Feelies’ “Doin’ it Again” still hits my ears like Ravi Shankar at the Concert for Bangladesh, only fuller. The Staples Singers did a fulfilling version of “Respect Yourself,” EMF did “Lies.” And as it would happen, one musician who they could never get, Bruce Springsteen, was David Letterman’s last NBC musical guest. (Springsteen said at a show I went to that he “looked forward to being on the David Letterman show.”)

But another musical guest, Cher, who was wanted on Letterman for a long time, didn’t sing when she finally accepted their invitation. I happened to go to be at the show she appeared on. But Cher had a special tape dedicated to her on my VHS; which has since been converted to DVD. “Dave” mentioned Cher running up quite a hotel bill; that they put her up for months and she lived fancy. So, he asked her directly “Why do you think it’s been so hard to get you on the show? Why do you rebuff all of our advances?” She didn’t balk: “Because I thought you were an asshole.” It caught everyone off guard, doubling us all over in pain. “Dave,” wiping the sweat from his brow with his tie, took it like a man. His spit take was on my tape the next day. But only half of her insult was.

Letterman deprecated himself by calling himself an asshole, with it coming out of left field several times. He wasn’t going to let her get the best of him. When the segment was over, the two stars embraced like they’d never had a quarrel.


VIDEO: Cher’s first appearance on Letterman

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Billy Sternberg

Billy Sternberg graduated from Syracuse University's Newhouse School. He bought national TV commercial ad time for American Home Products. Their brands ranged from Anacin to Chef Boyardee to Black Flag Roach Motel. After that, he bought national TV time at Ogilvy & Mather for American Express, Kimberly Clark and Owens Corning Fiberglas. Because of this he was gifted many tickets to many events.

One thought on “My Late Night With David Letterman Tapes

  • December 16, 2022 at 2:14 pm

    I went to the Daytime show, too. The show did like a zero rating so they took me to shut me up. Floyd Styles, from where ever was mentioned is Small Town News for what ever. But Styles thought they were flying him in. So they did. Everyone on the stage was wearing a Floyd Styles Day T-Shirt but the audience didn’t get anything. Today the audience doesn’t go home empty handed.


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