Great post, AI.
The one and only time I saw GSH perform was in June 1986 in Manchester, where I was living at the time. The '86 World Cup in Mexico was taking place, and a few of us were round at my boy's house in the late afternoon/early evening watching the classic France-Brazil quarter-final, which is still one of the greatest games I've ever seen. Several beers after the game had finished, someone says, "Hold up, Gil Scott-Heron's doing the International II tonight!" The immediate and unanimous decision was to roll up posse-deep in the hope the show wasn't sold out, which it thankfully wasn't. although the place was a good three-quarters full by the time Gil came on. He was on tremendous form, cracking sardonic jokes throughout, and had a truly commanding presence. An extended, unaccompanied version of "Space Shuttle", which was a new tune then, turned into a coruscatingly funny monologue on the (literal) fallout from the Chernobyl disaster affecting Europe, still a big news story. He didn't have a record out at the time, or even a label, so the material was a decent balance between the then-recent Arista output ("Gun", "B-Movie", "Washington DC", "Shut 'Em Down"), earlier classics ("Winter In America", "Johannesburg", "Lady Day & John Coltrane" and a gorgeous version of "Your Daddy Loves You"), and a few newer songs. I remember he actually had a Mancunian guitar-player in his band at the time, which went down particularly well with the crowd. It was a fantastic evening all round. The perception of Gil at the time by a lot of people in the UK was of someone rather worthy and earnest, whose music you listened to out of a sense of duty rather than for pleasure. Anyone who went to that show could have testified what an arse-backwards assessment that was. It's still one of the best and most memorable shows I've ever been to, and that's even after getting drunk as fuck and dancing until two in the morning at the club after Gil's set finished.
It's been heart-breaking to witness his decline over the last decade or so. To see such a giant of an artist brought down by the very ills he warned against is beyond depressing. I hope he manages to find his way back, because the world would be a smaller place without him in it.