Not a huge fan of any of his (too many) personas and (way too many) cheap tricks - there are very few songs he's actually ever done that are genuinely moving or where you can't see through his act (seeing through him is harder).
But Five Years is one of his very best songs and performances - "his brain hurts a lot" is about as honest as he ever got (mine too David) and here for one of the few times ever he actually sang - not crooned, not pretended to be Sinatra or Jagger or Anthony Newley or whatever the cabaret schtick was - his voice cracks, he's overwhelmed, he's sad by the tale he's telling.
From a guy I think was sort of a fraud a lot of the time well...........that's the greatest trick of all.
Not as big a fan of this period of Bowie's career as some people. A few great songs, but the albums on the whole are just okay/pretty good. Aladdin Sane and the Berlin trilogy are his high points. Hunky Dory would have been a bit more interesting to do for a poll.
One of my all-time favorites. Every song on here is a knockout and it's nearly impossible to pick. Ultimately had to go with "Five Years" though, one of Bowie's most raw, bare, and affecting songs. It plays like a beautiful, angst-ridden ballad, and it's gotta be one of the very best tracks he ever put out (which is saying a lot).