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I bought a Hustler magazine and boy was I disappointed

Posted on November 2, 2025 by Joke Poo

It wasn't about making money at all.

Okay, here’s my “Joke Poo” version:

Joke Poo: Crappy Investment

I bought a roll of toilet paper, thinking it would be a safe investment, and boy was I disappointed.

It completely went to sheet.

Alright, let’s dissect this joke.

Joke Breakdown:

  • Setup: “I bought a Hustler magazine and boy was I disappointed…” – Creates an expectation of something risqué or sexually explicit. The word “Hustler” evokes imagery associated with the magazine brand.
  • Punchline: “…It wasn’t about making money at all.” – This is a wordplay-based punchline. “Hustler” as a word implies someone who works hard to make money, a “hustle.” The joke subverts the expectation of the magazine’s content by contrasting it with the literal meaning of the word.
  • Humor Source: The humor arises from the surprise and incongruity. The juxtaposition of the magazine’s reputation with the literal definition of “hustler” creates the comedic effect. It plays on pre-conceived notions and expectations.

Key Elements:

  1. Wordplay (Hustler): The double meaning of “Hustler” (the magazine vs. someone making money).
  2. Expectation Subversion: Leading the audience to expect one type of content and delivering something completely different.
  3. Brand Recognition (Hustler magazine): The joke relies on the audience’s existing understanding of the magazine’s identity.

Comedic Enrichment:

Let’s play off the “making money” aspect of “hustle” and combine it with the Hustler magazine brand.

New Joke/Observation:

I went to a business seminar hosted by Hustler magazine. They promised to teach us how to “hustle” our way to the top. Turns out, their definition of “aggressive negotiation” involved a very different type of leverage. I thought they were going to teach us about mergers and acquisitions, but it was more about… well, mergers and acquisitions of a different sort.

Explanation of the New Joke:

  • It keeps the theme of money and “hustle.”
  • It exaggerates the incongruity of what one expects from a business seminar versus what one knows of Hustler magazine.
  • The double entendre “mergers and acquisitions” reinforces the contrast. It plays on the expectation of financial concepts and reveals a more salacious meaning.
  • It continues the subversion, twisting the initial premise.

Alternative: Witty Observation/Did You Know:

Did you know that Hustler magazine, despite its explicit content, has actually been involved in several First Amendment legal battles? Ironically, while they weren’t teaching anyone how to make money directly, they were spending a fortune defending their right to do so… and that took some serious financial “hustle.”

Explanation:

  • This observation uses a factual tidbit to create humor. Hustler is indeed known for defending free speech.
  • It ties the magazine’s legal history to the original joke’s “making money” theme.
  • It ends with the pun “financial hustle,” bringing it full circle.
  • It creates a humorous irony – fighting for the right to publish the magazine (and thus make money) required quite a bit of effort and expense.

This approach leverages the original joke’s components and adds new layers of humor through factual information, exaggeration, and double meaning.

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