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The Captain’s Red Shirt

Posted on September 12, 2025 by Joke Poo

Captain’s Red Shirt

The year was around 1890.
A pirate ship is traversing the Atlantic Ocean to the next bounty.

From the crow’s nest, the Lookout yells: “Captain! One enemy war ship ion the horizon!”

The Captain barks out orders:
– Arm the battle stations!
– and, First Officer, go fetch my red shirt

The First Officer brings the Captain his red shirt and asks: “Is this your lucky shirt?”

The Captain replies: “No, but if I were to be wounded in battle, I need our defenders to stay focused and not worry about me bleeding.”

They are victorious.

A few days later……

From the crow’s nest, the Lookout yells: “Captain! Five enemy war ships on the horizon!”

The Captain barks out orders:
– Arm the battle stations!
– and, First Officer, go fetch my red shirt

The First Officer brings the Captain his red shirt.

A similar situation, they are victorious.

A week later…..

From the crow’s nest, the Lookout yells: “Captain! Two Hundred enemy war ships on the horizon!”

The Captain barks out orders:
– Arm the battle stations!
– and, First Officer, go fetch my brown pants!

Joke Poo: The Accountant’s Beige Sweater

The year is 2024. A major accounting firm, “Bean Counters Inc.”, is gearing up for tax season.

From her cubicle, a Junior Associate wails: “Senior Partner! We’ve got a massive IRS audit scheduled for next week!”

The Senior Partner bellows:

  • Get all the documents prepped!
  • And, Debra, fetch my beige sweater!

Debra, the Junior Associate, brings the Senior Partner his beige sweater and asks: “Is this your lucky sweater?”

The Senior Partner replies: “No, but if they find a discrepancy, I need them to focus on the crumbs and coffee stains, not the millions in offshore accounts.”

They survive the audit, relatively unscathed.

A few weeks later…

From her cubicle, Debra cries: “Senior Partner! The Department of Justice is launching an investigation into our Enron account!”

The Senior Partner bellows:

  • Get the shredders warmed up!
  • And, Debra, fetch my beige sweater!

Debra brings the Senior Partner his beige sweater.

Again, they seem to weather the storm.

A month later…

From her cubicle, Debra screams: “Senior Partner! The FBI, the SEC, and 60 Minutes are all outside!”

The Senior Partner bellows:

  • Lock the doors!
  • And Debra… fetch my brown pants!

Okay, let’s break down this pirate joke and then enrich it with some comedic flotsam and jetsam.

Analysis of the Original Joke:

  • Setup: We’re established in a classic pirate setting, facing ever-increasing odds in naval battles. The recurring “red shirt” gag is established as a symbol of the Captain’s pragmatic leadership.
  • Punchline: The punchline subverts the established pattern. Instead of the red shirt, the Captain requests “brown pants,” indicating fear and impending… well, you get the idea.
  • Humor: The humor lies in the incongruity and the implied bodily function. It’s a classic fear-based joke playing on pirate stereotypes and the red shirt gag.

Key Elements:

  • Pirates: The setting and characters.
  • Red Shirt: The recurring symbol representing a means to conceal blood.
  • Escalating Threat: The increasing number of enemy ships.
  • Subverted Expectation: The brown pants instead of the red shirt.
  • Implied Incontinence: The reason for the brown pants.

Comedic Enrichment:

Let’s explore some ways to amplify the humor, either with a new joke or by adding some relevant (and funny) trivia.

Option 1: A New Joke (Playing on Pirate Logistics)

A pirate captain storms into the quartermaster’s cabin. “Blast it all, man! I need 200 pairs of brown trousers, immediately!”

The quartermaster, looking bewildered, replies, “200 pairs, Captain? That’s more than we have rum barrels! What in Davy Jones’ Locker is going on?”

The Captain sighs, “Let’s just say…the lookout spotted the Spanish Armada. And I’ve issued a new standing order: Prepare for boarding…and tactical trouser deployment!”

Why this works: It builds on the punchline of the original joke, extends the brown trousers gag, and inserts a humorous logistical issue related to pirate supplies.

Option 2: Amusing “Did You Know?” (Fact-Based Humor):

Did you know: While pirates are often portrayed wearing an eye patch, it wasn’t always for covering a missing eye? Some historians believe pirates strategically used an eye patch to keep one eye always adjusted to darkness. So, when they had to go below deck quickly, they could simply switch the patch to the other eye and see instantly! Perhaps that is what the captain meant by “brown pants!” Perhaps brown pants, were used to block the sun’s glare from certain unwanted outcomes!

Why this works: We tie in a genuine pirate detail with the joke. The idea that the real reason the captain wants brown pants is for a more tactical reason plays on the audience’s expectation.

Option 3: A Witty Observation

You know, that pirate captain was a genius. The red shirt was a clever tactic, but the brown pants? Pure psychological warfare. Imagine the terror of your enemies when they see your entire crew wearing brown pants. They’d think they were facing a particularly gassy and terrified hoard of cutthroats!

Why this works: This takes the dark humor of the joke and turns it into a funny observation about pirates with gas.

I hope these enrichments provide more humor.

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