Episode Overview

Title: Do Not Pass Go! (w/ Scotty Icenogle)
Release Date: April 17, 2025
Podcast: SmartLess Presents ClueLess
Host: Elliott Kaelin
Guest: Scotty Icenogle
Contestant: Sean Hayes

In Episode 145 of SmartLess Presents ClueLess, host Elliott Kaelin teams up with returning contestant Scotty Icenogle and special guest Sean Hayes for a lively exploration of the classic board game, Monopoly. This episode, aptly titled "Do Not Pass Go!", delves into Monopoly's rich history, its latest expansions, and features an engaging trivia competition intertwined with brainteasers and puzzles designed to test the contestants' knowledge and quick thinking.

Monopoly Expansions Discussion

The episode kicks off with an enthusiastic discussion about Monopoly's three new expansion packs, introduced to enhance and diversify gameplay:

1. Buy Everything Expansion

   • Scotty Icenogle describes it as the perfect addition for players aiming to "own the whole board," allowing them to acquire every property space available.

2. Free Parking Jackpot Expansion

   • Elliott Kaelin highlights this expansion for risk-takers: "Land on free parking, spin the wheel and boom. Cash in big. But don't get too comfortable because it's risky."

3. Go to Jail Expansion

   • Tailored for strategic players, this expansion transforms jail from a mere penalty into a tactical advantage: "Bribe, steal and collect corruption cards to mess with your opponents."

Notable Quote:
"Whether you're a risk taker, rule breaker, or money maker, Monopoly has three new expansion packs for you to explore."
— Scotty Icenogle [05:17]

Monopoly Trivia Round

Elliott initiates a Monopoly-themed trivia session, selecting the category "Monopoly tokens" through a spinner. The first question challenges the contestants to identify which token has never been part of the standard Monopoly set.

Question: Which of these has never been a token in the standard Monopoly game set?
Choices:

• T Rex
• Cannon
• Goose
• Sack of Money

Responses:

• Scotty Icenogle selects "Goose."
• Sean Hayes concurs with Scotty's choice.

Reveal:
Elliott confirms that the Goose has never been a Monopoly token, while the other options have appeared in various editions over the years.

Notable Quote:
"Monopoly has never had a goose shaped token."
— Elliott Kaelin [04:49]

Main Game: Do Not Pass Go

The heart of the episode is the "Do Not Pass Go" game, a word-guessing challenge where contestants must identify words and phrases ending with "GO." The objective is to accumulate points without "passing Go," i.e., without including letters beyond "GO."

Gameplay Highlights:

1. Round One:

   • Clues Included:
     • Company's symbol → Logo
     • Windy city → Chicago
     • Another word for jargon → Lingo
     • Pink waterfowl → Flamingo
     • Lotter-style game with numbered balls → Bingo
     • Crime comedy film by the Coen brothers → Fargo
     • Plastic building bricks → Lego
     • Villain in Shakespeare's Othello → Iago
   • Scores:
     • Sean Hayes: 4 points
     • Scotty Icenogle: 6 points

2. Round Two:

   • Clues Included:
     • Dizziness → Vertigo
     • Chain of islands → Archipelago
     • Kind of cheese similar to Parmesan → Asiago
     • Manufacturer of camper vans → Winnebago
     • Island forming a country with Trinidad → Tobago
     • Tree used as a memory supplement extract → Ginkgo
     • Trade ban → Embargo
     • Freud’s part of the mind acting as our conscience → Superego
   • Scores:
     • Sean Hayes: Gained 3 points
     • Scotty Icenogle: Gained 4 points

Notable Interaction:
When Scotty struggles with "Iago," Elliott humorously remarks, "He's the sidekick bird in Aladdin," leading Scotty to incorrectly guess "Hugo."

Notable Quote:
"Words always end in GO. You're not passing go because there's no letters after GO."
— Elliott Kaelin [07:34]

Mega Clue Round

As the competition intensifies, Elliott introduces the Mega Clue segment featuring more challenging words and phrases ending in "GO," each worth five points.

Mega Clues Included:

1. Russian novel made into a film starring Omar Sharif

   • Answer: Dr. Zhivago

2. One of opera's famous three tenors

   • Answer: Domingo

3. New Wave band founded by Danny Elfman

   • Answer: The B-52s (Note: In the transcript, Scotty incorrectly answers "Boingo Bongo" instead of "The B-52s," but the correct answer based on context would be The B-52s or possibly Oingo Boingo.)

4. A huge round of applause at the end of a play

   • Answer: Standing O

5. Fictional thief who sneaks around the world from Kiev to Carolina

   • Answer: Carmen Sandiego

Scores After Mega Clue:

• Scotty Icenogle: 27 points
• Sean Hayes: 22 points

Notable Quote:
"Carmen Sandiego."
— Sean Hayes [16:18]

Final Trivia and Conclusion

In the concluding segment, Scotty spins the spinner to select a category on Monopoly Special Editions, posing a final trivia question:

Final Question:
Which of these pop culture figures have never had their own themed Monopoly Special Edition?
Choices:

• Deadpool
• Ted Lasso
• Paris Hilton
• The Beatles

Responses:

• Scotty Icenogle selects "The Beatles."
• Sean Hayes opts for "Ted Lasso."

Reveal:
Elliott clarifies that Paris Hilton has never had her own Monopoly Special Edition, while the other options have been represented in various themed sets.

Winner Announcement:
With a final tally of Scotty Icenogle at 27 points and Sean Hayes at 22 points, Scotty emerges victorious in this episode's Monopoly showdown.

Notable Quote:
"Monopoly brings so people together, friends and relatives, cars and thimbles, top hats and little dogs."
— Elliott Kaelin [17:12]

Key Takeaways and Insights

• Monopoly's Enduring Appeal: The episode underscores Monopoly's lasting popularity and its ability to evolve through new expansions and themed editions, keeping the game fresh and engaging for both new and veteran players.

• Strategic Gameplay: The "Do Not Pass Go" game exemplifies how classic board games can inspire creative and educational content, blending trivia with word puzzles to challenge and entertain participants.

• Community and Competition: The dynamic between the host and contestants highlights the spirit of friendly competition and the communal joy derived from shared gaming experiences.

Additional Notable Quotes

• "Never pass and go. The words end in go, the ones that you're going to guess so you don't have to."
  — Elliott Kaelin [07:41]

• "I cannot make this clear. You can't go past Geo. Just don't answer it."
  — Elliott Kaelin [08:03]

• "Good, good. I'm happy for you, listeners at home."
  — Elliott Kaelin [16:53]

Conclusion

Episode 145 of SmartLess Presents ClueLess offers a delightful blend of nostalgia and intellectual challenge, celebrating Monopoly's iconic status while providing listeners with engaging content that tests their knowledge and problem-solving skills. Through spirited competition and insightful discussions, Elliott Kaelin, Scotty Icenogle, and Sean Hayes deliver an entertaining homage to one of the world's most beloved board games.