Bob Dylan’s “Leopard-Skin Pill-Box Hat” is not explicitly a protest song. The sultry, bluesy electric guitar that mingles with the vocals throughout gives the song a swagger not associated with the political folk songs of Dylan’s earlier acoustic period. Politics and rock and roll are not a mismatch here, however; they are indeed a sly way of reaching exactly the sort of audience that Dylan is ridiculing. The album Blonde on Blonde was ranked ninth on the Billboard 200 in 1966, and the single itself made it onto the Billboard 100 the following year (according to Wikipedia). The status-obsessed and materialistic sort of person that Dylan derides throughout the song is exactly the type who would be purchasing the most popular rock and roll albums of the day.
“Leopard-Skin Pill-Box Hat” begins as a commentary on the absurdity that the latest fashion trends often involve. He questions the cost of the hat in the second stanza, wanting to know “If it’s really the expensive kind,” because of course in the fashion world, money paid directly correlates with status earned. “You know it balances on your head just like a mattress balances on a bottle of wine”, Dylan comments nonchalantly, as though such a bizarre image is a typical and rather enviable appearance. Like many fashion statements of previous decades, the pillbox hat does in retrospect look rather ludicrous today.
Dylan’s social commentary digs a bit deeper as the song progresses. The leopard-skin pill-box hat gives its wearer increasing power over men. Dylan finds himself competing for the subject with his own doctor; then, finds her with another boyfriend altogether, who he claims must love her only for her hat, rather than, ironically, her money. Dylan makes fashion ridiculous by exaggerating just the sort of scenario fashion advertisements so often portray: a woman who captivates men with the allure of her beauty, which is only fully realized by some fashion garment or another. Dylan wants his listeners to recognize the trap that he sees the advertising industry setting for them: the idea that the right apparel is the one most important step to being successful.
This particular song is not one of Dylan’s most famous or influential songs, but it is a song that he still deems important. In 2009, a charity project called War Child: Heroes approached 15 music icons and asked each to select a current musician to cover one of their favorite classics. Bob Dylan chose musician Beck, and arranged for him to play “Leopard-Skin Pill-Box Hat”. The obsession with fashion and status is as relevant today as it was when Dylan first wrote the song. Moreover, the song holds the same ultimate message in both the modern Beck version and older Dylan version – that true success cannot be acquired through money or appearances.