I Used to Work in Chicago

Song Meaning

The lyrics recount a former department store employee's mischievous past in Chicago. Each verse describes an interaction with a female customer, starting innocently enough. However, the narrator's interpretations quickly turn suggestive. The consistent refrain, "I used to work in Chicago," emphasizes a past job that ended for reasons implied to be scandalous. The core tension in these lyrics stems from the stark contrast between the polite, everyday requests of customers for items like a "girdle" or "hat," and the narrator's wildly inappropriate, pun-driven responses. This creates a mischievous, almost rebellious, humor as the narrator repeatedly acts on the double entendre, knowing full well the implications. The scenarios escalate, moving from a girdle to a ticket, each more audacious than the last. The song's cleverness lies entirely in its consistent use of homophonic wordplay. Each verse sets up an innocent customer request, only for the narrator to twist the item's name into a sexually suggestive action. This predictable structure builds anticipation, making the listener lean in for the next crude punchline. The simple, direct language makes these linguistic flips even more impactful, highlighting the narrator's deliberate misinterpretation. These lyrics are effective because they masterfully employ a simple, bawdy humor rooted in linguistic subversion. The repeated line, "I'll never go there anymore," serves as a humorous acknowledgment of consequences, implying the narrator's actions led to their dismissal or banishment. This blend of innocent setup, crude wordplay, and implied comeuppance creates a memorable, laugh-out-loud narrative that relies entirely on the listener's ability to catch the double meaning.