As word game enthusiasts, we’re all pretty familiar with wordplay. Whenever we see a crossword clue ending in a question mark, for example, we know there’s some cleverness afoot, and our synapses start firing in double time.
But witty wordplay isn’t unique to the world of puzzles. Throughout history there have been some spectacularly talented—and hilarious—musicians who have packed their lyrics with puns and double entendres, and have gone way outside the box to conjure unique rhymes. There were the old masters, like W.S. Gilbert and Stephen Sondheim, younger wordsmiths, including such acts as Flight of the Conchords and Garfunkel and Oates, and everyone in-between. (I’m looking at you, Weird Al). We have long held an attachment to musical artists who can tickle our funny bone and our cerebral cortex at the same time.
In this article, we’ll focus on three masters of the craft—one from each of the last three generations.
Tom Lehrer
Many younger readers may be asking, “Tom Le-who?” But the truth is that there may never have been an individual more adept at weaving together memorable melodies and scathing humor. Lehrer was not particularly prolific. In a career lasting just two decades, he wrote and performed fewer than 50 songs. But
