Just when you thought the best policy was to ask relatively easy trivia questions to keep more listeners playing along, something like You Can’t Win comes along. The syndicated talk show Free Beer and Hot Wings created a seven-month trivia game that paid off to one listener that was able to answer cohost Kelly Cheese’s five trivia questions. But these were not ordinary questions.

Each question was a riddle with a story behind it and Kelly was the only person that knew the answers.  The contest started when Kelly challenged the rest of the show by claiming she could write better trivia questions than the guys for their daily Dumber Than The Show game.

Here’s how it sounded on the final day in December when a listener got all five answers correct:

A couple of notes:

  • The key to this game is having just one cast member that knows the answer. Make it fun for the rest of the cast to play along!
  • Expect trash-talk! The show’s faithful followers were highly critical of Kelly at the beginning but in a good way! The controversy soon turned to curiosity and ultimately to a sticky daily listening occasion.
  • For details on how this game works (and why), check out the full explanation guide (with more audio examples) here.
  • The show kept track of incorrect answers for each question on their website here.

Well done! And very successful! In fact, the show intends to bring it back for an encore performance in the near future.

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