I wrote my longest Overthinking It post in years – perhaps ever – giving a deep read of Wyclef Jean’s three-year-old pop hit, “Sweetest Girl (Dollar Bill).”
Wyclef makes use of a triple-antanaclasis here with three different meanings of the word “bill.” The first, the most common one throughout the song, is a bill as in currency — the “dollar dollar bill, y’all.” The second is a bill as in an invoice for services, like a water bill — “if they got to pay the bill.” The third is the bill as in the marquee of performers — “Tonight Wyclef, Akon, Weezy on the bill.”
What’s the effect of this identity rhyme? It ties into the theme that we’ll explore later in the chorus — that the presence of cash in the world is inescapable. Every aspect of your life touches on a bill. Wyclef, Akon and Lil’ Wayne are on the bill tonight (the marquee). Why? So they can make the bills (dollars) to pay the bills (invoices). It’s almost as if this single syllable rules everything around them.