The term booby meaning a stupid person dates to about 1599. From Patient Grissil, a comedic play written 1599-1603:

Then, mage a pooby fool of Sir Owen, indeed. God’s plude, shall!

It probably comes from the Spanish bobo, also meaning a foolish or stupid person, as well as being the name of the type of bird—which are slow, stupid, and easy to kill. It is sometimes suggested that it comes from the German bube, which is sometimes used in the same sense, but the Lower German form, which would be closer to English, is boeve or boef, which makes the connection implausible.1

The sense meaning breast appears in the late 17th century. The exact origin of this sense is uncertain, but it is likely related to the German bübbi, or teat. From Thomas D’Urfey’s 1690 New Poems:

The Ladies here may without Scandal shew Face or white Bubbies, to each ogling Beau.2

The Oxford English Dictionary, 2nd Edition marks this sense as “Obs. or dial.” But numerous citations have been found through to the present day, showing that the big dictionary is mistaken on this point.3

The spelling boobie appears by 19164 and boob by 1929-31.5

1Oxford English Dictionary, booby, n.1, 2nd Edition, 1989, Oxford University Press, accessed 26 Dec 2008 <>.

2OED2, bubby1, <>.

3Historical Dictionary of American Slang, v. 1, A-G, edited by Jonathan Lighter (New York: Random House, 1994), 280-81.

4Harold Wentworth, American Dialect Dictionary (New York: Thomas Y. Crowell Company, 1944), 41.

5HDAS, v. 1, 232.

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