SmartLess Presents ClueLess

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

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.

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.”

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)

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 |

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.

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.