Meaning of "Up On The Hill" by Jimmy Buffett

The song's lyrics paint a vivid picture of a wealthy social class living in opulence on a hill, detached from the realities of the rest of society. The portrayal of these individuals as "big cheeses" who own the "cool breezes" suggests a sense of entitlement and arrogance. The emphasis on charming personalities, cute names, and wealth as the main factors for success on the hill highlights the superficiality and shallowness of this elite group. The references to traditional values like blue-blood lineage and a cautious attitude towards anything new reveal a sense of elitism and an aversion to diversity. Ultimately, the song critiques the privileged class for their ignorance, materialism, and detachment from the struggles of everyday people while highlighting the absurdity of their illusions of grandeur.