This song is about cross-dressers who come to New York City and become prostitutes. "Take a walk on the wild side" is what they say to potential customers. Each verse introduces a new character. There is Holly, Candy, Little Joe, Sugar Plum Fairy, and Jackie. The characters are all cronies of the infamous Andy Warhol Factory, as was Lou. Reed had an empathy for these characters that comes through in the song, as he struggled with his sexuality for most of his life. His parents even tried to "cure" his homosexuality when he was young. With this song, Reed presented a completely different view of gender roles in rock.
"Little Joe" refers to Joe Dallesandero, who was also one of Andy's kids in the factory. He was in several films by Warhol. Sugar Plum Fairy is the nickname of actor Joe Campbell.
"Holly," "Candy," and "Jackie" are based on Holly Woodlawn, Candy Darling, and Jackie Curtis. They are all real drag queens who appeared in Warhol's 1972 movie Women In Revolt. Woodlawn also appeared in Warhol's 1970 movie Trash, and Curtis was in Warhol's 1968 movie Flesh. Said Reed: "I always thought it would be kind of fun to introduce people to characters they maybe hadn't met before, or hadn't wanted to meet."
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