Los Angeles, CA
In 1987, my family had just gotten a VCR and I used it to tape Letterman on (Mondays thru Thursdays) because it came on NBC at 12:30pm and I was in bed by the time reruns the Odd Couple on WPIX ended by 11:30pm. I'd wake up super early and watch Letterman's monologue and Top 10 list before I went to school.
Here is a rare glimpse of Jerry Garcia on late night TV. It was in the fall of 1987, while the Grateful Dead were in the middle of their "comeback" run at Madison Square Garden. Jerry was clean and sober after surviving a nasty diabetic coma. Sober is the key component here. That's the only reason you'd find him... 1) in a suit jacket, and 2) participating in the big machine of televised entertainment.
Check out this grainy video from Jerry's appearance on Letterman with Bob Weir. In the opening clip (I assumed it was the cold open), Jerry and Dave are playing Scrabble and hilarity ensues.
In the second part, Bob Weir and Jerry sit in with Paul Schaefer and the band to cover Bob Dylan's I Paint My Masterpiece.
In the last segment of the video, Jerry and Bobby get interviewed by Letterman. Letterman tries to talk about their new album (at the time In the Dark with the radio hit Touch of Grey was released). You could see Jerry get a little bored, a little pranksterish, a little snippy (directed at Dave) at times, and he's also brutally honest about the Dead's propensity of blowing their big gigs (e.g. Woodstock and the Pyramids). The funniest part featured Bob Weir attempting to do a "parlor trick" by picking up Jerry using only two fingers from Dave, Paul, and stagehand Biff Henderson.
And here's the Dead playing MSG the night before Jerry & Bobby taped Letterman. They opened up second set with Bertha...