Boards of Canada - Inferno (40 years in)
David Bowie - Blackstar (54 years in)
HUM - Inlet (31 years in)
Scott Walker - The Drift (41 years)
Bob Dylan - Time Out Of Mind (and some others that followed)
big Lenny C releasing You Want It Darker 50 years into his career, fucking dropping dead and then dropping Thanks For The Dance. unmatched
Lambchop - Punching The Clown (40 years)
John Cale - MERCY (60 years in). Seriously, give it a listen!
Coincidentally, I was listening to Graceland a day or so ago and was wondering whether that was the furthest an artist had been into their career to drop a record that could very easily be considered their best or most successful (in terms of sales/reception).
Nick Cave - Ghosteen
The Cure - Songs of a Lost World
Low just miss out by a year, shame
Grant Hart - The Argument
Robert Forster - Songs To Play (38 years after the Go-Betweens’ debut)
Converge formed in 1990 so both their albums this year could count.
Deftones - Private Music (37 years in)
Johnny Cash - American series (particularly fond of American IV myself)
My Bloody Valentine - mbv (30 years in)
Dinosaur (Jr). Knocking it out of the park since 1985.
Robert Wyatt - Shleep, 30-something years after he started playing with Soft Machine
Donald Fagen
Good one that.