On September 17th, 1987, in the midst of a 5-night run at Madison Square GardenGrateful Dead guitarists/vocalists Jerry Garcia and Bob Weir made an appearance with David Letterman. The national TV spot marked their second time as guests of Late Night with David Letterman following an appearance in 1982.

The late-night TV spot came at an exciting time in the Grateful Dead’s history. As Weir noted to Letterman, the band had been going for 23 years at that point, but had just notched their first “right out of the shoot” Platinum-certified record with 1987’s In The Dark. After decades as counterculture heroes, In The Dark and, particularly, the music video-assisted explosion of single “Touch of Grey”, had made the band “overnight sensations,” catapulting them squarely into mainstream consciousness.

Letterman mused, “So 23 years, and is it safe to say that this—and these may not be terms you care about, necessarily—but in terms of commercial success, this is your biggest moment right now, huh?”

Weir responded reflexively with a mischievous, child-like giggle, the kind of response you only give to something profoundly silly. Jerry Garcia and Bobby Weir looked at their watches—even though Jerry didn’t actually have one on. “What time you got?” joked Jerry. “Proudest moment of my life,” replied Weir, smiling.

“I’m quietly proud at this moment, yes,” Garcia finally conceded. Their amusement at Dave’s initial question was honestly realized and echoed the feelings of fans who had followed them for years. By this point, the Grateful Dead had already achieved so much. They had built the most devoted following in the history of live music, championed a revolutionary approach to performance and improvisation, essentially (and unwittingly) invented “viral marketing” by way of tape trading. They had consistently sold out amphitheaters, arenas, and stadiums around the country.

They had even gone to Egypt to perform in the shadows of the Pyramids, a feat that seemed almost unfathomable to Letterman. Bobby and Jerry looked back on it with a positive, though tempered, outlook. When Letterman asked about their experience in Egypt, Bobby responded casually, “That was great.” “We played terrible,” Jerry chimed in, “but the trip was great.”

When Letterman pressed them about their poor playing, Jerry responded with a laugh, “We usually do pretty bad on the big ones. We played terrible at, uh, Woodstock and, you know, Monterey Pop Festival. All the milestones…” He went on to talk about how a new electrical ground their sound guy at Woodstock used caused their instruments to shock them throughout the performance.

Most artists would be upset or regretful about such an unfortunate circumstance at such a significant show. But Jerry and Bobby just laughed. The Grateful Dead weren’t “most artists.” They had great shows, and they had not-so-great shows. It didn’t matter—they played thousands of them, and they would continue to do so either way.

Why should they care if the supposed “big shows” weren’t their best shows? Why should they feel like this moment was their band’s alleged “biggest moment”—because they had some catchy videos on MTV? Their attitudes said it all. The Grateful Dead had built their legacy their own way, on their own terms. If you’re just catching on now…well, whose fault is that? Welcome to the party. You ain’t seen nothin’ yet.

Below, you can watch Jerry Garcia and Bob Weir’s full 1987 David Letterman appearance, including Jerry’s amusing cold-open Scrabble game with Dave and their performance of Bob Dylan‘s “When I Paint My Masterpiece” with Paul Shaffer and The World’s Most Dangerous Band:

Jerry Garcia & Bob Weir on Late Night with David Letterman – 9/17/87

[Video: LoloYodel]

[Originally published 9/17/18]