On September 17th, 1987, in the midst of a five-night run at Madison Square GardenGrateful Dead guitarists Jerry Garcia and Bob Weir made an appearance with David Letterman. Their live performance and interview on the popular talk show marked their second time as guests of Late Night with David Letterman, following their famous More Fun Than A Frog In A Glass Of Milk!” appearance in 1982.

The 1987 late-night appearance came during an exciting time for the Dead and their fans. As Weir noted to Letterman during the interview, 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 underground counterculture heroes, In The Dark–particularly, the hit video for “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, childlike giggle, the kind of response you only give to something profoundly silly. Garcia and 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.

Related: Listen To Bob Weir’s Isolated Guitar From Grateful Dead’s Final Show At Berkeley’s Greek Theatre On This Day In 1989

When Letterman pressed them about their notable memories and biggest over the years, 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…” Garcia and Weir also 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.

Relive Garcia and Weir’s 1987 Letterman interview below, which began with a performance of Bob Dylan‘s “When I Paint My Masterpiece” alongside Paul Shaffer and The World’s Most Dangerous Band.

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

[Video: BetaGems]

[Originally published 9/17/17]