Azzonlino, Aggie; Silvey, Linda; and Hughes, Barnabas, editors, Mathematics and Humor, National Council of Teachers of Mathematics, 1978.
Baker, Robert A., A Stress Analysis of a Strapless Evening Gown, Prentice-Hall, 1963.This collection of cartoons is a real gem. Old math jokes and lots of new ones. There is everything from "Tom Swifties" (e.g., "Proofs are necessary," reasoned Tom.) to the new book shelf (e.g., 10,000,000 Random Numbers Arranged in Ascending Order). Every teacher should have a copy of this!
Yes, one essay here does give a pseudo-scientific analysis of why a strapless evening gown stays up. Also take a look at "Mathmanship," the art of placing unsuspected obstacles in the path of the reader of a mathematical text, such as intentional typos.
Birdwood, Wilbur P., Euclid's Outline of Sex, Henry Holt and Co., 1922.
I know you won't believe this, but I found this by accident! Was browsing the math section of a used book store in Berkeley and the next section was on Sex. This was right between them. It's a Freudian interpretation of Euclid.
Boas, Ralph P., Jr., Lion Hunting & Other Mathematical Pursuits. A Collection of Mathematics, Verse, and Stories, The Mathematical Association of America, 1995.
This collection of papers by Boas is loaded with gems. Lots of interesting elementary papers; in addition, there are hundreds of tidbits to amuse you.
Dudley, Underwood, Mathematical Cranks The Mathematical Association of America, 1992.
Look here for information about people who have really nutty ideas about mathematics.
Eves, Howard W., In Mathematical Circles, Mathematical Circles Revisited, Mathematical Circles Squared, Mathematical Circles Adieu, Return to Mathematical Circles, Prindle, Weber, and Schmidt, 1969, 1971, 1972, 1977, 1988 respectively.
This is the most wonderful collection of stories about mathematics and mathematicians that I have ever seen. Go find these books and read them. They will provide enjoyment and a wealth of stories for teachers to tell in class.
Fadiman, Clifton, Fantasia Mathematica, The Mathematical Magpie, Simon and Schuster, 1958 and 1962 respectively.
Fiction with a mathematical theme is what you will find here. The "No-Sided Professor" is a classic. Also a nice collection of poetry and limericks.
Gardner, Martin, Knotted Doughnuts and Other Mathematical Entertainment's, Freeman, 1986.
This is just one of the dozens of books that Gardner has published about mathematical recreations. They don't fit in the "humor" category, but I could not resist them here.
Harris, Sidney, What's So Funny About Science?, William Kaufman, Inc., 1977.
Cartoons dealing with science and a few with mathematics.
Krantz, Steven J., Mathematical Apocrypha, MAA 2002.
There are plenty of tales here that will make you smile.
Linderholm, Carl E., Mathematics Made Difficult, World Publishing, 1992.
This is mathematics written in the style of Saint Thomas of Aquinas. Lots of play on advanced mathematics. The humor is subtle, but the title is super.
Moritz, Robert Edouard, Memorabilia Mathematica; or the Philomath's Quotation Book, reprinted by the Mathematical Association of America.
Anecdotes, aphorisms, and quotations from famous mathematicians. Dover has reprinted this as "On Mathematics and Mathematicians." It is the classic book of quotations about mathematics. A delightful book of quotations. You can find one here for any aspect of mathematics.
O'Brien, Katherine, Excavation and Other Verse, The Antheonsen Press, 1967.
Some of these poems are mathematical. I like "Einstein and the ice-cream cone," "Valentine," and "Undefined Terms," but my favorite is "Aftermath" which deals with what happens to a mathematicians library after they die: "Now Hardy's a treasure and Banach a pleasure / and the Knopps a delight for the mind." Rich allusions indeed for those who have read their books.
Paulos, John Allen. Mathematics and humor, University of Chicago Press, 1980. BGSU: PN6149.P5P3
Robson, Ernest, and Wimp, J., Against Infinity. An Anthology of Contemporary Mathematical Poetry, Primary Press, 1979.
Schaaf, William L., A Bibliography of Recreational Mathematics, National Council of Teachers of Mathematics, 1955, 1970,1973, 1978.
These bibliographies contain thousands of references to papers in easily accessible journals dealing with such topics as calculating prodigies, geometric fallacies, the Mobius strip, angle trisections, mathematics and music, games of all sorts, etc.
Scherr, George H., editor, The Best of The Journal of Irreproducible Results, Workman Publishing, 1983.
Did you know that -1 is the largest integer? Check out the clever proof here.
Schmalz, Rosemary, Out of the Mouths of Mathematicians, The Mathematical Association of America, 1993.
A new book of quotations, with a wealth of material from the past two decades. You will find everything from stories about Von Neumann's lightening quick mind to what should be called the World Sequence.
Michael Stueben, Diane Sanford, Twenty Years Before the Blackboard: The Lessons and Humor of Mathematics Teacher, MAA 1988.
Steward, Ian, and Jaworski, John, Seven Years of Maifold, 1968-1980, Shiva Publishing Limited, 1981.
Swann, Howard, and Johnson, John, Prof. E. McSquared's original fantastic & highly edifying calculus primer, W. Kaufmann, 1977.
Alas, this is a real calculus book. But with all the cartoons, you might be interested in taking a look.
Weber, R. L., A Random Walk in Science, and More Random Walks in Science, Crance Russak & Comp. Inc., 1973, 1982.
Two delightful anthologies of scientists at play includes satire, anecdotes, cartoons, verses, and tongue-in-cheek notes, with some serious scientific asides mixed in. The first has long been a favorite of mine. My personal favorites are the anecdote about the ballistics pendulum of Lord Kelvin and the proof that all horses have an infinite number of legs.
Weller, Tom, Science Made Stupid, Houghton Mifflin Co., 1985.
Unfortunately, or perhaps fortunately, there is no chapter here on mathematics. But lots of nutty stuff. The evolution chapter is my favorite.
http://www.math.utah.edu/~cherk/mathjokes.html