SmartLess Presents ClueLess

Episode 213: Odd Throuples/Coupled Up
Guests: Moshe Kasher & Natasha Leggero
Date: February 2, 2026
Host: Elliott Kalan

Overview

In this bite-sized, puzzle-packed episode, Emmy-winning writer Elliott Kalan welcomes comedy power couple Moshe Kasher and Natasha Leggero for a themed slate of brainteasers—perfectly timed for Valentine’s Day. The puzzles revolve around wordplay, celebrity mash-ups, and couple-based clues, testing Moshe and Natasha’s wit, competitive banter, and teamwork. Along the way, listeners get hilarious asides about marriage dynamics, surprising celebrity anecdotes, and a reaffirmation that, even when a game feels confusing, humor and teamwork carry the day.

Key Discussion Points and Insights

1. Introduction & Guest Banter

[01:20–02:25]

• Elliott introduces Moshe and Natasha, highlighting their real-life marriage and comedy chops.
• The guests joke about Valentine’s Day, Lincoln’s Birthday, and their own connection to Lincoln via Illinois.
• Moshe facetiously claims he supported the North in the Civil War, setting the tone for playful historical asides.

  “At the time, it was a controversial stand, but I think history has shown that you were right to do that.” — Elliott ([02:06])

2. About the Endless Honeymoon Podcast

[02:25–02:53]

• Natasha explains their podcast’s premise: relationship advice and comedic “roasting.”
• “We roast people’s love lives. We try to help them...Essentially mocking the love of other people.” — Moshe ([02:47])
• Elliott gushes about their show, segues into a conversation about games and puzzles.

3. Puzzles and Family Dynamics

[03:07–04:28]

• Natasha admits to being “more on the clueless side of things.”
• Moshe details their daughter’s love of riddles, and the family’s divide between pretending enjoyment vs. honest reactions.

  “In our family, it’s about shutting down the illusion that we’re charmed.” — Moshe ([03:43])

• Natasha claims to prefer Zen koans and hates puns: “Something that I could, like, think about for a few years, and then finally, you know, the sound of one hand clapping...” ([03:58])
• Elliott jokes that their daughter should bring Zen koans to the dinner table.

Segment 1: Opening Puzzle – Name Blend Riddle

[04:44–07:05]

Riddle:

“Can you name an iconic basketball player and an iconic pop star whose names, when you put one in front of the other, reveal the name of a legendary folk singer?”

• Natasha and Moshe reason through basketball and pop star names.
• Moshe gets the answer:
  LeBron James + Taylor Swift = James Taylor
• Elliott and Natasha discuss Carole King’s musical connection to James Taylor.

Memorable Exchange:

“LeBron James, Taylor Swift, the two greatest pop culture icons of our era.” — Moshe ([06:24])

Segment 2: Game One – Odd Throuples

[08:10–14:37]

Premise:

Combine last name of one celeb with first name of another to form a new celebrity’s name.

Sample Rounds:

• George (Wham) + Pollock = Michael Jackson ([09:08])

  • Natasha instantly nails it. Moshe quips about “Zen co-op” from earlier.
  • Moshe jokes about competition in their marriage.

    “All a competition.” ([09:30])

• Jake (YouTuber/boxer) + Simon (reality judge) = Paul Simon

  • Natasha takes a while, Moshe gives the clue that they had dinner with Paul Simon and Bill Maher.
  • Shared anecdote: Paul Simon’s humble reflection on writing “The Sound of Silence.”

    “I remember when I wrote it, I thought, huh, that’s better than the songs I usually write.” — Paul Simon (relayed by Moshe, [10:53])

• Man (surrealist) + Charles (natural selection theorist) = Ray Charles

  • Natasha stumbles through Charles Darwin before landing on Ray Charles.
  • Moshe jokes about Natasha’s Ray Charles knowledge being limited to soda commercials.

• Diana (princess) + Ross (presidential hopeful) = Diana Ross

  • Moshe and Natasha quickly solve it.

• Celine (Titanic singer) + Warwick (Willow actor) = Dionne Warwick

  • “We’re fudging the spelling here,” Elliott clarifies ([13:52]).
  • Moshe jokes, “Because I got the right one, baby.”

Bonus Question:
In 1985, all these answer celebs participated in USA for Africa’s “We Are the World.”

• Natasha recommends the documentary, highlighting Bob Dylan’s awkwardness and Stevie Wonder’s guidance.

  “Bob Dylan...does an impression of Stevie Wonder doing an impression of Bob Dylan.” — Natasha ([15:08])

Segment 3: Main Game – Coupled Up

[16:51–23:38]

Premise:

Guess two-word phrases where the last letter of the first word is the first letter of the second word (e.g., “snow White”).

Highlights:

• Moshe initially unsure about the format, then catches on fast.
• Natasha excels at solving clues, often not quite following the letter-link logic.
• Moshe jokes, “At this point, I’m officially self conscious about how difficult this is for me.”

Questions and Answers:

1. “Person with seven tiny roommates”: Snow White ([18:56])
2. “Small glass vessel for an experiment”: Test Tube ([19:23])
3. “Five out of five is usually the best this can be”: Star Rating (Moshe/ Natasha say Star Review, which is accepted) ([20:09])
4. “Electronic substitute for a percussionist”: Drum Machine ([20:15])
5. “Extreme close up, wide shot...”: Camera Angles ([20:44])
6. “Someone with excellent vision”: Eagle Eye ([21:19])
7. “Batman’s nickname”: Dark Knight ([21:33])
8. “Words that begin children’s rhyme or a 911 call”: (Missed) Answer: Hello Operator ([23:10])

Moshe jokes:

“You got seven out of eight questions. Now you’ve made it through the gauntlet of life as a couple. I apologize. Life ends now.” ([23:32])

Segment 4: Mega Clue & Key Relationship Lesson

[23:47–25:20]

Mechanics:

Unscramble the shared linking letters from each answer to find a secret to a successful relationship:

• Letters: W, T, R, M, A, E, K, O
• Answer: TEAMWORK

Natasha swiftly solves it:

“I know what it is…Teamwork.” — Natasha ([25:19]) “Some people build their marriages on competition. Some people build it on teamwork. We’ll see who wins in the end.” — Elliott ([25:20])

Moshe jokes their family motto is:

“Teamwork makes the dream work. And communism is a good idea in theory.” ([25:40])

Notable Quotes & Memorable Moments

• On Family Puzzle Dynamics:

  “We’ve heard this one before. Come to the table with something better next time.”—Moshe ([03:43])

• On Competition:

  “The game of our marriage is...it’s all a competition.”—Moshe ([09:30])

• On Folk Musicians and Time:

  “Folk singers...Joni Mitchell, Carole King.”—Natasha ([06:14]) “And they don’t make folk singers anymore.”—Natasha ([06:11])

• On Marital Teamwork:

  “Teamwork makes the dream work.”—Moshe ([25:40])

• On Letting the Answers Come to You:

  “You’re like Paul Simon. The answers are just coming to you.”—Elliott ([21:45])

• On Nostalgic Commercials:

  “You got the right one, baby. Uh huh.”—Elliott & Moshe ([12:25])

• On Relationship Advice and Competitiveness:

  “Today, Elliot, you joined our team, and I think you can agree it felt pretty good.”—Moshe ([26:48])

Key Timestamps for Segments

• Guest Banter & Puzzle Philosophy: [01:20–04:44]
• Opening Music/Name Riddle: [04:44–07:05]
• Odd Throuples Game: [08:10–15:39]
• We Are the World trivia & doc anecdote: [14:37–15:39]
• Coupled Up Game: [16:51–23:38]
• Mega Clue & Teamwork Lesson: [23:47–25:20]
• End-of-Show Recap & Promotion: [25:32–27:24]

Conclusion

This episode blends fast-paced wordplay with authentic relationship banter. Listeners learn that the world of puzzles—like marriage—is best navigated with humor, acceptance of each other’s strengths and weaknesses, and a strong dose of “teamwork.” Amid jokes about family dynamics, pop culture history, and famous folk singers, Natasha and Moshe’s comedic chemistry shines, making even obscure word games feel warm and welcoming.

For more laughs and relationship wisdom (or at least the mockery of it), check out Moshe and Natasha’s “Endless Honeymoon Podcast.”

Listener’s Takeaway:
Even if you don’t ace every riddle, there’s a place for you at the table—as long as you bring a little teamwork (and maybe a Zen koan).