This is a fun problem from the 1949 Eureka magazine.
“The following problems were set at the Archimedeans’ 1949 Problems Drive. Competitors were allowed five minutes for each question. [This is problem #9.]
A pillar is in the form of a truncated right circular cone. The diameter at the top is 1 ft., at the bottom it is 2 ft. The slant height is 15 ft. A streamer is wound exactly five times round the pillar starting at the top and ending at the bottom. What is the shortest length the streamer can have?”
See the Pillar Wrapping Problem