Frank Sinatra - High Hopes

Frank Sinatra was one of the most famous singers of all time. He was at his peak in the 1940's, but was still big in the 1950's, when he performed this song. 

Temperament that it hits on: Sanguine 

High Hopes hits on my sanguine because sanguines are typically pretty hopeful and never give up. 

This song is fairly atypical of Sinatra, whose work is usually slow, serious, and boring (let's start the controversy!). Now this is about the only song of his that I like, but Sinatra's success spanned more than half a century, so I guess he did pretty well for himself.