What: Cole Porter’s ribald number “Brush Up Your Shakespeare,” from the 1948 Broadway musical Kiss Me, Kate, here performed by Teddy Kempner and Jack Chissick in the 1999 revival:

Why: After dominating Broadway in the 1930s, Cole Porter suffered a debilitating horse-riding accident in 1937, and the musical world started to pass him by. But the success of Rodgers and Hammerstein’s Oklahoma! spurred him to write his masterpiece, Kiss Me, Kate. Armed with a brilliant book by the feuding married couple of Samuel and Bella Spewack, Porter set Shakespeare’s The Taming of the Shrew to music, debuting soon-to-be-classics like “Too Darn Hot,” “So In Love,” and “I Hate Men.” The show-stopper featured two nameless gangsters showing their command of the Bard’s works, all to the effect of brusquely chatting up “dainty debbies.” The gangsters fired off pun after Shakespearean pun: “Flatter her,” for example, rhymes with “Cleopatterer.” And what must the audience of 1948 have thought of the shocking line “Kick her right in the Coriolanus?” Porter had the song end three times, each time garnering applause from the crowd. When you orchestrate two curtain calls in the middle of a number, you know you’ve got something great.

Impact: Kiss Me, Kate ran for more than 1,000 performances, by far Porter’s longest. It won the very first Tony Award for Best Musical, and Porter won for Best Composer, and the Spewacks for Best Author. It was made into a 1953 film featuring James Whitmore and Keenan Wynn as the newly named gangsters Slug and Lippy. But hey, here’s the stunner: The film and subsequent stagings of the musical feature far less scandalous lyrics than the original Broadway version. Think you know the song? Check out Porter’s original lyrics. Imagine what the song would have been like with the line “If she still calls her lover a Jonah/Give her two gentlemen of Verona.” The mind reels.

Personal Connection: I wanted to write this entry for a while, but I had to hold off till this year’s MIT Mystery Hunt was over. In a melodious puzzle by thedan called Sorry, Wrong Number, I “sung” a couple lines of Kiss Me, Kate‘s “Tom, Dick, or Harry” to the tune and style of “Brush Up Your Shakespeare.” Though the song was my suggestion, I think Dan edited this specifically so he could have a clip of me saying this word.

Other Contenders: the revolutionaries set Paris ablaze in “Do You Hear the People Sing?”, from Les Misérables; Donald O’Connor endeavors to “Make ‘Em Laugh” (boldly plagiarizing Porter’s “Be a Clown”) in Singin’ in the Rain; Trekkie Monster explains it all in “The Internet is for Porn”, from Avenue Q; a freakin’ helicopter lands on stage during “Last Night of the World,” from Miss Saigon (a.k.a. Evon and Mike’s first date).

Note: I restricted myself from filling up the Other Contenders solely with Porter songs, but if I hadn’t, I’d’ve included Bing and Frank predicting our collision with Mars in High Society‘s “Well, Did You Evah?”; the Seven Lively Arts classic “Ev’ry Time We Say Goodbye” (here performed by Simply Red); and the song with the funniest punch line ever, Hi Diddle Diddle‘s “Miss Otis Regrets” (this being the other Kirsty MacColl/Pogues collaboration referred to in this entry).