Old Bob had to sing about this countryside feature (4)
I believe the answer is:
hill
This clue might be a double definition.
'old bob' is the first definition.
The definition and answer can be both man-made objects as well as being singular nouns.
Maybe you can see a link between them that I don't see?
'to sing about this countryside feature' is the second definition.
Although both the answer and definition are singular nouns, I can't see how one could define the other.
'had' acts as a link.
Can you help me to learn more?
(Other definitions for hill that I've seen before include "High point, but not a mountain" , "Canvasser of opinions" , "high ground" , "Mound (of mole, ants)" , "See 14" .)