Bob Dylan returned to the Grammy Awards in early 2000, not as a nominee (no new music produced to speak of in the past couple of years), but as a presenter for Album of the Year. Dylan won that award in 1998, and he co-presented with Lauryn Hill (who won in 1999). Presumably the previous winner is brought back to give away the statue the next year, but perhaps Dylan was double-booked in 1999? I don’t know.
I can’t find a complete clip of the presentation. You can see Hill reading the winner if you click through to the Grammys site here. Dylan is kind of funny here, pointing (I think) at Carlos Santana. Did he know who the winner was, or was he just suggesting that it should go to his friend? Likely the latter.
It must have been a big moment for Santana, who won a slew of awards that night. Lauryn Hill was one of the guest stars on Supernatural, and he toured extensively with Dylan in 1993, so it was a pretty ideal set up in terms of the people up there to give him the big prize.
Earlier in the show Santana performed “Smooth” with Rob Thomas. This song won three awards. Do you remember Matchbox 20? I had totally forgotten that they existed until I clicked on this video, and now it is stuck in my head. I’m terribly sorry.
Sorry, not much to this one – just an early 2000 Dylan cameo. Bit of a bizarre jacket, if you ask me. (Hill, of course, looks great).