176 - Mad Hatter Day (Mini Episode)

Summary

SmartLess Presents ClueLess

Episode 176: Mad Hatter Day (Mini Episode)
Released: October 6, 2025
Host: Elliott Kalan
Producer: Devin Tory Bryant

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Episode Overview

This Mad Hatter Day mini episode celebrates Lewis Carroll’s iconic character (and his famous hat) with puzzles inspired by wordplay and Victorian trivia. Emmy-winning writer Elliott Kalan guides listeners—and this season’s contestant, Sean Hayes (in absentia)—through whimsical trivia, “double T” brain teasers, and a light dip into the strange history of the phrase “mad as a hatter.” It’s bite-sized puzzling with SmartLess’s signature silliness and wit.

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Key Discussion Points & Insights

What is Mad Hatter Day?

• Mad Hatter Day is October 6th, referencing the “10/6” tag on the Mad Hatter’s hat from “Alice in Wonderland,” which means 10 shillings, 6 pence—the price of the hat, not a date.
  • Quote:
    • “Good thing the tag doesn’t say 10 45. We’d be celebrating this holiday on October 45th. And usually I’m busy enjoying November at that time of the year.”
      — Elliott Kalan (01:46)

The Origin of “Mad as a Hatter”

• The phrase comes from 18th-century hat making, where mercury nitrate was used to turn animal fur into felt. Prolonged exposure led to severe mental health issues—hence “mad as a hatter.”
  • Quote:
    • “Mad as a hatter is a colorful phrase that’s a throwback to a simpler time when poisoning your employees was just considered good business.”
      — Elliott Kalan (02:35)

The Hat Price Decoded

• “10/6” means ten shillings and six pennies, which Kalan cheerfully notes is about $73.43 today.
• Quote:
  • “Which seems expensive for a hat, but not enough money to justify getting mercury poisoning.”
    — Elliott Kalan (03:09)

Puzzle Time: Tea Party (The Letter “T”)

• Premise: Clues lead to two-word phrases where both start with the letter “T”.
• Round 1 Answers:

  • Tall tale (A real whopper)

  • Table tennis (Ping pong)

  • Treasure trove (A collection of valuable things)

  • Tire tracks (After a car skids)

  • Tick tock (A reminder that time is running out)

  • Memorable line:

    • “I’m going to give you a moment to take a sip of tea, the drink or the letter.”
      — Elliott Kalan (04:01)

Round 2: More Challenging “Double T” Phrases

• Round 2 Answers:

  • Terrible twos (Phase of childhood that’s rough on parents)

  • Time travel (What you need the flux capacitor for)

  • Take two (A second attempt at something)

  • Triple threat (A writer, director, producer)

  • Thompson Twins (Band who sang “Hold Me Now” in 1984)

  • Quote:

    • “The terrible twos. They’re terrible. There’s two of them, there’s two T’s, and the T stands for terrible.”
      — Elliott Kalan (08:52)
    • “For three people in the audience, perhaps a better clue would have been 'our identical unhelpful allies of Tintin, Snowy and Captain Haddock.'”
      — Devin Tory Bryant (09:56)

Final Banter and Wrap

• The hosts riff on the idea of Tintin’s adventures if they had ‘80s new wave flair.
• Cheery encouragement, regardless of listener performance.
  • Quote:
    • “If you were any more perfect, people would get jealous.”
      — Elliott Kalan (10:41)
• Plug for upcoming Season 2 of ClueLess—coming “very soon.”

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Notable Quotes & Moments (with Timestamps)

• Celebrating Mad Hatter Day:
  “Surely one of the top 10 books about a little girl who falls in a hole.”
  — Elliott Kalan (01:46)

• On hat costs and mercury:
  “Prolonged exposure to this answer may result in you learning something. Also dangerous.”
  — Elliott Kalan (03:09)

• Introducing the puzzle format:
  “Today’s game is called Tea party. The letter T. It’s a play on letters.”
  — Elliott Kalan (03:37)

• On the band clue:
  “They had a hit in 1984 with the song Hold Me Now. The. That’s the Thompson twins. Yes.”
  — Elliott Kalan (09:51)

• Meta, end-of-episode thanks:
  “I’d settle for half your attention and the rest in cash.”
  — Elliott Kalan (10:47)

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Important Segments & Timestamps

| Timestamp | Segment | |-----------|-----------------------------------------------------------| | 01:03 | Elliott welcomes listeners, pitches the episode premise | | 01:46 | Explanation of Mad Hatter Day and its quirky calendar tie | | 02:35 | Brief history lesson: “mad as a hatter” | | 03:09 | The meaning and inflation-adjusted cost of “10/6” | | 03:37 | “Tea Party” puzzle game—Round 1 clues and answers | | 07:25 | Return from ads, setup for Round 2. | | 08:31 | Round 2 “Double T” clues and answers | | 10:41 | Encouragement/banter as answers are revealed | | 10:47 | Thank-yous and Season 2 teaser |

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Episode Flow & Tone

• Warm, irreverent, clever, friendly—true to the SmartLess style, with Elliott Kalan’s dry humor and a light touch of trivia nerdiness.
• The puzzles are both fun to play along with and gleefully explained, making for a genuinely inviting experience—no matter how much “tea” you’re drinking.

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For New Listeners

This mini-episode is a showcase of whimsical wordplay, playful trivia, and cheerful camaraderie—perfect for anyone looking for a quick, brainy laugh, sprinkled with cultural and literary tidbits. Whether you nail the puzzles or just enjoy the ride, it’s a charming, fast-paced pick-me-up.

Transcript

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[Elliott Kaelin]

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[Elliott Kaelin]

Medium it's important to keep an open mind, but not too open. Once my mind was so open that a bunch of stuff fell out of it. This is Clueless. Clueless. Clueless. I'm Clueless. Welcome to Smartless Presents. Clueless, the puzzle podcast that puts its pants on two legs at a time. I'm your host, Elliott Kaelin, and I know what you did last summer, and it sounds like it was really fun. Producer Devin, what's today's order of business?

[Devin Tory Bryant]

Well, Elliot, season two of Clueless is still getting waxed and detailed. So this week we've got another mini episode.

[Elliott Kaelin]

That sounds good to me. Today's miniature episode is being released on October 6th, so we're celebrating Mad Hatter Day. As all fans of Victorian nonsense literature know, the the Mad Hatter is one of the guests at the mad tea party in Alice in Wonderland by Lewis Carroll. Surely one of the top 10 books about a little girl who falls in a hole. Why October 6th? Because that's what the tag on the Mad Hatter's hat says. 10 6. Good thing the tag doesn't say 10 45. We'd be celebrating this holiday on October 45th. And usually I'm busy enjoying November at that time of the year. But for our first question today, can you tell me what does 106 mean? Really mean?

[Devin Tory Bryant]

Elliot, I'm concerned the listeners Will get mad if they don't have time to think about that. So could you spill the tea about why those hatters were so mad?

[Elliott Kaelin]

Your wish is my command. Producer Devin. The phrase mad as a hatter is thought to have come from the 18th century Hat making industry. Back then, milliners used toxic mercury nitrate to soften animal fur into felt for hats. Prolonged exposure to this dangerous sounding chemical was, unsurprisingly, very dangerous and could lead to a range of mental issues from trouble speaking to hallucinations. So there you have it. Mad as a hatter is a colorful phrase that's a throwback to a simpler time when poisoning your employees was just considered good business.

[Devin Tory Bryant]

I think it's time to expose the audience to the answer to our first question.

[Elliott Kaelin]

Okay. But prolonged exposure to this answer may result in you learning something. Also dangerous. That 106 on the Hatter's hat isn't a date but the price of the hat. An old timey British currency that's 10 shillings and 6 pennies. Adjusted for inflation, that hat would $73.43 today. Which seems expensive for a hat, but not enough money to justify getting mercury poisoning. Listeners, did you get the answer? If so, you've won our grand prize. Another game.

[Devin Tory Bryant]

Yay.

[Elliott Kaelin]

Today's game is called Tea party. The letter T. It's a play on letters. Yes, Tea party. I'm going to give you two rounds of clues to some two word phrases in which both words start with the letter t. Can you identify all these double T phrases? Here's your first round. Your clues are a real whopper. Ping pong. A collection of valuable things. You might see them after a car skids. A reminder that time is running out. Again, those clues are a real whopper. Ping pong. A collection of valuable things. You might see them after a car skids. And a reminder that time is running out. I'm going to give you a moment to take a sip of tea, the drink or the letter. And then I'm going to give you the answers to those clues. Have you had your tea? How was it? Excellent. We're not that great. You know what? Let's just focus on the answers, shall we? The first clue was a real whopper. And the double T phrase is tall tale. That's right, a real whopper. Tall tale. You can't believe it. The next clue was ping pong. And I'm sure you guessed that it was table tennis. That was a double P for a double T. It starts with p and that rhymes with t and that stands for Table tennis.

[Devin Tory Bryant]

There you go.

[Elliott Kaelin]

Next clue. A collection of valuable things. That's a treasure trove. This one's a little harder because the T doesn't make a T sound, but a t ch sound. Ds can do that. They're very versatile. The next clue. You might see them after a car skids. Tire tracks. That's right, tire tracks. The tracks of a tire. And finally, in this round, a reminder that time is running out. Tick tock. Yeah. This is the sound of a clock ticking away. Time running out. And unfortunately, time has run out for this round. We'll have more clueless for you right after the next two word T. A t Mercial Tinteruption.

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[Elliott Kaelin]

Welcome back to Smartless Presents Clueless, the puzzle podcast. Whose favorite kind of tea is? Mr. It's time for round two of our mad tea party. The letter tea that is tea party. And this one gets a little more challeng. Can you tell me what two word double T phrases these clues describe? The first clue is phase of childhood that's rough on parents. Phase of childhood that's rough on parents. The next clue what you need the flux capacitor for 80s kids remember what you need the flux capacitor for? And then the next clue. A second attempt at something. A second attempt at something that was my second attempt at reading that clue. The fourth clue. A writer, director, producer. What two word T phrase would mean a writer, director, producer. And then finally, the final clue in this more challenging round. They had a hit in 1984 with the song Hold Me Now. Eighties kids will also remember.

[Devin Tory Bryant]

Yes.

[Elliott Kaelin]

What two word tea phrase had a hit in 1984 with the song Hold Me Now. So I guess in some ways this was an 80s edition.

[Devin Tory Bryant]

Yeah. It seems to me.

[Elliott Kaelin]

Of tea party. Now I'm going to go through those clues again, but here's the difference. I'm going to tell you the answers. So if you still want time, pause the podcast, take another sip of tea, or whatever you're drinking. Could be just straight vinegar. That's. I mean, if that's what you want to drink, I won't stop you. But now here are the answers to those clues. The first clue. Phase of childhood that's rough on parents, that's the terrible twos. We've all been there, whether a parent or a child. The terrible twos. They're terrible. There's two of them, there's two T's, and the T stands for terrible. The next clue, what you need the flux capacitor for. Again, 80s kids remember, it's time travel, of course, from back to the future. Yes. So you would need time travel. That's your two T word phrase. A second attempt at something. That two T phrase would be take two. Gonna get it on take one. Now it's time for take two. We've had several take twos during the recording of this episode. The next clue. A writer, director, producer. What double T phrase is a writer, director, producer? That's a triple threat. A triple threat is the phrase we're looking for. And then finally, the other ones you could probably try to figure out through some sort of reasoning. But this last one, you just kind of have to know the answer.

[Devin Tory Bryant]

Yeah.

[Elliott Kaelin]

They had a hit in 1984 with Hold Me Now. The. That's the Thompson twins. Yes.

[Devin Tory Bryant]

Or for three people in the audience, perhaps a better clue would have been our identical unhelpful allies of Tintin, Snowy and Captain Haddock.

[Elliott Kaelin]

Yes. And the answer would still be Thompson twins.

[Devin Tory Bryant]

It still would be Thompson twins.

[Elliott Kaelin]

Yes. But not the same Thompson twins that I hit in 1984. Withhold me now. Exactly. Tintin was not hanging out with pop stars.

[Devin Tory Bryant]

No. Well, no. Erger died, I think a little too soon for that. If he'd made it to the 80s, I wouldn't put it past him.

[Elliott Kaelin]

Yeah, yeah. I think you're right, Devin. Producer Devin, I think you're right. That Tintin, he would have had some new wave adventures. Would have had a lot more 1980s new wave styling to it. Listeners, did you get the answers? If not, that's a good thing. If you were any more perfect, people would get jealous. We're all out of the most important tea of all time. But before we go, I'd like to thank you, the listener, for giving us all of your attention. Though frankly, I'd settle for half of your attention and the rest in cash.

[Devin Tory Bryant]

And I'd like to remind everybody that our all new Clueless Season two is coming very soon. Very soon.

[Elliott Kaelin]

So soon. So soon. But first, we'll be back next week with more Smartless Presents Clueless Miniature. Until then, I'm your host, Ellie Kaelin, and if anyone asks, I was never here.

[Devin Tory Bryant]

Clueless, you have been listening to Smartless Presents Clueless, a Smartless Media production in association with SiriusXM. Your host is Elliot Kaelin, who also writes our scripts. Your producer, editor and engineer is Devin Tory Bryant, who is me. I also write all the music and sound effects. Today's puzzles were written by Jason Reich. Executive produce are Elliott Kaelin, Sean Hayes, Will Arnett and Jason Bateman. Executive producers for Smartless Media are Richard Corson and Bernie Kaminsky. Remember to follow, subscribe, rate and review the show. It really helps. That's all for now. We will see you again for more.

[Elliott Kaelin]

Smart Bless media.

[Magic: The Gathering Announcer]

Magic, the Gathering and Marvel Team up for a magic set featuring your friendly neighborhood Spider Man. Add iconic superheroes and Supervillains from over 60 years of Spider man comics to your magic game. This set gives you the power of Spiderman. But remember, with great power comes great responsibility. Visit magic.wizards.com to learn more about how to suit up with Spider Man. That's magic.wizards.com to learn more about the Gathering. Marvel's Spider Man Swing into the game.