I’m thinking mostly in threes but you can do more if you want.
Lets get the obvious Dylan one out of the way Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde.
But I honestly think Bjorks late 90s run is insanely good: Post, Homogenic, and Vespertine. Honestly cant pick a best out of them and they are all very creative ambitious works which are insanely well produced.
Quite like Pavements run as well: Slanted and Enchanted, Crooked Rain, Crooked Rain, and Wowee Zowee.
Wilco: AM through A Ghost is Born. 5 very good to classic albums. Plus you can add in Kicking Television (live) and the first two Mermaid Avenue albums, giving you a run of 8 with no duds.
Pixies: first four (or five if you count Come on Pilgrim/the Purple Tape).
Fall would probably be Live at Witch Trials-Hex Enduction Hour for a pure run, ‘Room To Live’ isn’t quite as amazing as those, but if you count it their run could last into Bend Sinister at least
Silver Jews until LM,LS are all pretty fantastic in their own way, though Bright Flight may be a slightly less good album
(maybe not best ever but fuck it probably ‘underrated’ (it’s not even))
Lenoard Cohen’s last 3 records are very good. Currently listening to ‘Old Ideas’ and I enjoy it as much as some of his classics