It’s hard to imagine how the expression “more fun than a barrel of monkeys” came about, however it seems to have been a cause of great amusement over the generations.
In the Milwaukee Journal of July 27, 1938 the newspaper ran an article entitled, “Zoo Curator To Live On Island With 50 Monkeys For Medical Experiments.” The headline sounded outrageous and in keeping with the headline, Steven M. Spencer wrote:
If anything is “more fun than a barrel of monkeys” it must be a whole island of monkeys with a few apes thrown in for good measure. And if anyone is capable of raising monkeys and apes on an island and deriving amusement and useful knowledge therefrom, it would be Primatologist Michael I. Tomilin, whose gruff and dour Russian exterior masks a rich fund of wit and an unusual aptitude for scientific “monkey business.”
In 1913, French mathematician Émile Borel — whose speciality at that time was hyperbolic geometry and special relativity — used monkeys as central characters in his research, “Mécanique Statistique et Irréversibilité.”
Concevons qu’on ait dressé un million de singes à frapper au hasard sur les touches d’une machine à écrire … [translation: Let us imagine a million monkeys typing haphazardly on typewriters …”
It was the predecessor of the infinite monkey theorem that believes that a monkey hitting keys at random on a typewriter keyboard for an infinite amount of time will likely write something worth reading. Of course, the idea of a million monkeys sitting behind typewriters and working diligently at creating literary works is, in itself, a funny concept.
But getting back to the saying, more fun than a barrel of monkeys, the Los Angeles Timescarried a news article on February 18, 1896 entitled, “At The Play House” that reported:
… the merry little dwarf, is as funny as a barrel of monkeys when he does nothing but walk around the stage …
Just a few months earlier, the Chicago Daily Tribune ran a story on September 28, 1895 about the Republican Convention in Syracuse, New York that stated that the affair was “more fun than a barrel of monkeys.”
The saying was obviously used by people from different class distinctions. And the ease with which the saying was used in the story indicates that it was part of every day speech among people of different social classes.
For those not familiar with the toy, the standard Barrel of Monkeys® consists of a large number of individual monkey pieces, each about 7cm by 5cm in size. Each monkey has its arms extended in a hook shape in opposite directions. These arms can easily be interlinked to form a chain of monkeys, which is the intended use of the toy. Imprinted on the barrel are instructions for a couple of simple games.