64 Word Play Trivia Questions (From Mischievous To Outlandish)

Written by:
Eli Robinson
September 15, 2022

Are you good at thinking on your feet?

Do people often tell you that you have a quick wit?

If so, then you probably excel at word play trivia.

Word play trivia questions require you to think outside the box to find the right answer.

This type of trivia often includes puns, riddles, and tongue-twisting teasers.

Word play trivia quizzes are the perfect way to test your wit and see how fast you can think under pressure.

So, if you're feeling up for a challenge, we've got 64 word play trivia questions for you.

Before we explore the word play trivia questions and answers, we want to share a bit about Water Cooler Trivia with you.

Each week, Water Cooler Trivia can deliver brain-testing trivia quizzes straight to your inbox.

Oh, and the best bit?

We offer a four-week free trial - so you can explore everything Water Cooler Trivia has to offer without commitment.

64 Word Play Trivia Questions (From Mischievous To Outlandish)

  1. What two rhyming words summarize the following phrase? A tiny amount of a kitchen cooling device.  Answer: Smidge fridge
  2. What word means the following two things? A polyhedron formed by connecting a polygon to an apex or a game show that often included a number in its official title and won nine Daytime Emmy Awards.  Answer: Pyramid
  3. What two rhyming words summarize the following phrase? A gatherer and organizer of large, dangerous jungle felines.  Answer: Leopard shepherd
  4. What two rhyming words summarize the following phrase? A zippered piece of warm outerwear for a Serena Williams tool.  Answer: Racket Jacket
  5. What two rhyming words summarize the following phrase? To rapidly drink not just a large amount of hot liquid, but the vessel containing the liquid as well.  Answer: Chug mug
  6. What pair of rhyming words describes the following phrase? An easily deceived, foolish remnant of a removed tree.  Answer: Stump chump
  7. What two rhyming words summarize the following phrase? A sweet, Southern, bourbon-centric drink covered with the national flower of the Netherlands.  Answer: Tulip Julep
  8. What education-related word has two distinct meanings both related to books? The first is simply an organized listing of books (often at the end of a piece of research) and the second is a more systematic description of books as physical objects.  Answer: Bibliography
  9. What two-word rhyming phrase could mean the following? Trefoil found surrounding the Capitol in Delaware.  Answer: Dover Clover
  10. What pair of rhyming words describes the following phrase? A comfortable piece of lounging furniture for a green-skinned trashcan denizen.  Answer: Couch Grouch
  11. What two-word rhyming phrase could be used to describe a person who runs at high speed over short distances, but only during one of the four seasons?  Answer: Winter sprinter
  12. A requirement that driver's license applicants get an opportunity to register to vote earned The National Voter Registration Act of 1993 what rhyming nickname?  Answer: Motor Voter
  13. Fitness has a surprisingly large number of meanings. Of course there is the state of health and well-being, and then biological fitness is an individual's ability to propagate its genes. There's also the product Fitness which is produced by Nestle and is what type of food?  Answer: Cereal
  14. What two rhyming words summarize the following phrase? The charity network whose motto is "service above self," and a person who witnesses signatures on official documents.  Answer: Rotary Notary
  15. What rhyming brand of low-calorie meals did Stouffer's introduce in 1981 in response to consumers' desires for diet dinner options?  Answer: Lean Cuisine
  16. What word has both of the following meanings? A tightly bound bundle or the surname of the actor who played Dick Cheney in the 2018 film "Vice."  Answer: Bale
  17. Howard Stern is a proponent of what product, a stool that is placed next to the toilet in order to improve the user’s posture and reduce stress? It has a two word rhyming name. The first word-y refers to your posture, and the second word-y is a childish term for the toilet.  Answer: Squatty Potty
  18. _____ on the ______. Fill in the first blank with the last name of the British character who played Bilbo Baggins in Peter Jackson’s Lord Of The Rings films. Fill in the second blank with a type of stove, and you get an alternate spelling of what country western standard?  Answer: Holm On The Range
  19. If a beaver built a barrier in a pond to protect itself from a submarine’s missiles, what commanding phrase might the beaver exclaim?  Answer: Dam The Torpedos
  20. If there were a boat vacation for small cats of the family Felidae, it might share its name with what famous actor?  Answer: Tom Cruise
  21. A 1983 Lewis Gilbert film about an alcoholic professor, played by Michael Caine, who mentors the 1940s actress who starred in “Gilda” would have what three word “before and after” movie title?  Answer: Educating Rita Hayworth
  22. If the 19th century wild west showman and bison hunter switched careers and became an SNL cast member turned star of “Meatballs” and “Lost In Translation”, what three-word “before and after” name would he be?  Answer: Buffalo Bill Murray
  23. "Presbyterians" is not just a religious denomination -- it's also an anagram of the name of what singer of "Toxic" and "Gimme More?" First and last name required.  Answer: Britney Spears
  24. She'll only pay pennies and dimes for a kiss, but her whole soul for a wish. So go the weird economics of what Carly Rae Jepsen hit that anagrams to MY ABLE CAMEL?  Answer: Call Me Maybe
  25. "Round Mound of Rebound" was a college nickname for what NBA All-Star whose name anagrams to SKY REACH BALLER?  Answer: Charles Barkley
  26. What two rhyming words summarize the following phrase? A rainy-day invertebrate writhing uncomfortably.  Answer: Worm Squirm
  27. "Dog doo good god!" is a sentence that reads the same backwards and forwards. This is an example of what literary device?  Answer: Palindrome
  28. A "lemniscate" is a fancy word for what symbol that is used to express something without end?  Answer: Infinity symbol
  29. What word is partially defined by MacMillan Dictionary as “a party or special event” and is a Floridian town originally built by the Walt Disney Company in 1994?  Answer: Celebration
  30. What Swiss watchmaking company is a contraction of the phrase “second watch”?  Answer: Swatch
  31. What word is spelled with a “Q” in the United Kingdom, is derived from a Greek word meaning “sweet root” and is Ronald Reagan’s favorite Jelly Belly jelly bean flavor?  Answer: Licorice
  32. A bronx bomber, an absentminded scribble, and a man who places importance on physical appearance and refined language come together to form what song and American standard?  Answer: Yankee Doodle Dandy
  33. Without a U, it's a tree of the willow family. With a U in the middle, it's a song sung by Glinda in the Broadway show "Wicked." What are the two words?  Answer: Poplar and Popular
  34. Named for a Nashville hotel and perfect for a pick-me-up, what American coffee brand anagrams to ME SEXUAL HOWL?  Answer: Maxwell House
  35. A palindrome is a word or phrase that reads the same forwards and backwards; what is the corresponding term for words that become different words when read backward, such as STRAW and WARTS?  Answer: Semordnilap
  36. If you combine a word meaning the opposite of “old”, and a shirt that athletes wear that links them to their team, you get what 30th state alphabetically in the US?  Answer: New Jersey
  37. You get six tries to guess a five-letter word. That's the gist of what hot internet video game of 2022 that anagrams to EW LORD?  Answer: Wordle
  38. A saying attributed to Jesus, and the disrespect from a honey insect. Both can help you form what word?  Answer: Beatitude
  39. If someone suggested you walk 5,280 ft in a man’s shoes before judging him, what familiar distance term did this person probably mean to say?  Answer: Mile
  40. What is a monkey’s favorite low-end luxury clothing and accessories retailer? They imagine an entire Republic filed with a certain fruit, even if it is already owned by Gap.  Answer: Banana Republic
  41. A person locked into a schedule, or a monster formed out of a nun’s vestment. They both might be described with what familiar three-word phrase?  Answer: Creature Of Habit
  42. What word for a group of lions also sounds like the past tense word for inquiring into a person’s private affairs?  Answer: Pride
  43. If the reign in Spain falls mainly on the ______, then King Ferdinand’s reign would’ve likely ended in what kind of land, flat with few trees?  Answer: Plain
  44. A new word for topics related to marijuana could be the same as what process of forming objects out of ceramic material with high heat?  Answer: Pottery
  45. Obsidian, charcoal, pepper, crows, soot. These are just a few colorful items that might go on what list, perhaps curated by James Spader?  Answer: The Blacklist
  46. If, on “The White Album”, the Beatles said “you say you want to turn 360 degrees, well, you know, we all want to point back the same way,” they might be referring to a full version of what “R” geometric movement?  Answer: Revolution
  47. If a stinging insect were to be compressed by a mechanical press, what musical note might describe this newly skinny insect?  Answer: Bee Flat
  48. If Isaac Singer, 19th century inventor and founder of the Singer Sewing Machine Company, did some vocals on album produced by Miles Davis, with saxophone by John Coltrane, he could be called The ______ Singer. Fill in the one word blank.  Answer: The Jazz Singer
  49. If you had a long, thin, flat piece of wood to be used for building materials, but the wood was made of the ace of spades and the two of clubs, people might think you have what paper pulp product often used in shipping boxes?  Answer: Cardboard
  50. If a “S” red food fish with omega-3 fatty acids is identical to another batch, it could be also be called same-on in addition to what?  Answer: Salmon
  51. If the actress Cybill Shepherd somehow became embroiled in the war between the Northern United States and the Confederacy that occurred from 1861 to 1865, her name could be ______ Shepherd. Fill in the one word “C” blank, a word used to refer to that war.  Answer: Civil Shepherd
  52. What two rhyming words summarize the following phrase? An even-tempered, secure piece of household furniture.  Answer: Stable table
  53. If you saw some peat moss, and then you saw that same moss again, you might call it ______ moss. Fill in the one word “R” blank, also a word for saying something again that has already been said.  Answer: Repeat Moss
  54. Take the name of the UK's monarch from 1702 to 1707 and add a letter that can also mean the number 10. What word meaning a building extension do you get?  Answer: Annex
  55. Which two rhyming words could describe a petrifying pixie?  Answer: Scary Fairy
  56. The star of "Taken" and Mr. Payne of One Direction have given names that anagram to the name of what West African country?  Answer: Mali
  57. What word could mean the people in the stadium cheering on the football team and the handheld wind-makers they’re using to stay cool?  Answer: Fans
  58. Which two rhyming words describe a utensil you use for eating a pig?  Answer: Pork Fork
  59. Cobb County's Truist Park is the home stadium for what Major League Baseball team that anagrams to NAVAL BASE TART?  Answer: Atlanta Braves
  60. Add one letter to "Las Vegas" to get the title of what 2013 film, in which Michael Douglas, Robert De Niro, Morgan Freeman, and Kevin Kline play a group of friends having one final bachelor party?  Answer: Last Vegas
  61. What rich EU country anagrams to RUB EX MOGUL?  Answer: Luxembourg
  62. What two rhyming words summarize the following phrase? A hat a bunny nun would wear.  Answer: Rabbit Habit
  63. Which two rhyming words could describe having an ache in your thinking organ?  Answer: Brain Pain
  64. Which two rhyming words describe a gritty beach grain with no taste?  Answer: Bland Sand

What makes word play trivia so engaging?

For starters, it's the perfect way to test your lateral thinking skills.

Lateral thinking is all about looking at things from a different perspective - something that comes in handy when trying to solve puzzles and riddles.

It's also a great way to improve your problem-solving skills.

Word play trivia often requires you to think outside the box to find the right answer.

And, as we all know, the ability to solve problems quickly and efficiently is a valuable skill in both our personal and professional lives.

What are the best word play trivia questions?

The best word play trivia questions are the ones that make you think, laugh, and scratch your head all at the same time.

They're the ones that take you on a mental rollercoaster ride as you try to figure out the answer.

And, they're the ones that leave you feeling both satisfied and triumphant when you finally get it right.

If you're looking for some word play trivia questions that fit these criteria, then you've come to the right place.

Whether you're looking for a quick warm-up or a challenge that will really test your brain power, we've got you covered.

Where can you find word play trivia questions?

Finding word play trivia questions is easy.

Simply head on over to Water Cooler Trivia.

Water Cooler Trivia is a platform dedicated to providing trivia quizzes that are both fun and challenging.

We just so happen to have a whole section devoted to word play trivia.

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How can create the perfect word play trivia quiz?

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