Comment by beezlewax
Not the poster you asked but I'd say.. Start at or near the beginning. Later stuff has some gnarly sounding synths and arrangements that might not sound all that palatable to the modern ear (very 80s).
For me I first heard him via his album "Songs of Love and Hate". I found it in my dads record collection after a funeral of a close family member.
It's still my favourite.
> synths and arrangements that might not sound all that palatable to the modern ear
Are you referring to I'm Your Man? Because I'd say that it's his single most accessible collection of songs, and that his adoption of modern instrumentation was a genius move. The backing track for "First We Take Manhattan" sounds like New Order!