[citation needed] Applewhite moved to New York City in 1977 to work for St. Martin's Press, where she learned numerous offensive jokes, which her boss encouraged her to write down.

In a 2011 article in Harper's Magazine, Applewhite wrote that her collection of jokes quickly grew, and she would ask her coworkers and friends if they knew any others.

In a satirical vein, an installment of the comic strip Bloom County featured a book with a title similar to Truly Tasteless Jokes, portrayed as an inspirational text read by members of a counterculture resembling the hippies of the 1960s, but espousing conservative views considered typical of the Reagan era in American politics.

[4] Critic Edward Rothstein, analyzing the books' success for The New York Times, wrote, "... the telling of a joke brings into the light of society that which is hidden; it creates a marriage between the respectable and the unacceptable.

Actually, however, the rendezvous takes place in full daylight, with prejudices and fears displayed for the pleasure of thousands, and the point being made may not be as obvious as it at first appears.

"[4] In 2017, the rapper Eminem claimed the book was representative of his sense of humour, saying, "...[Truly Tasteless Jokes is] all fucked up shit; it makes me laugh — and that kind of stuff is where my brain goes.