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Q. What's pink and hard in the morning?A. The Financial Times crossword.
Describe "A game of using clues to fill in words and phrases into overlapping horizontal and vertical lines on a grid -- 9 and 6 letters" here.
As a hobby in fiction, crossword puzzle solving shows that the character is intelligent and good with words--or wants people around him to think he is. Some common motifs are:
- The know-it-all who does his puzzle in ink.
- The character fills in a set of wrong words that have to do with the plotline; usually this is to show that they're distracted.
- The person who constantly asks the other person in the room, "What's a 11-letter word that means 'mercenary captain?'"  Generally seen as someone who wants to be thought of as smart, but isn't quite making it. If they're asking, "What's a three-letter word that means 'feline?'", the character is meant to be not too bright at all.
- "Cheating" by looking in the next day's newspaper or the back of the magazine--absolute rotter.
- If the character does Sudoku instead, it connotes that the character is trendy and up on popular culture. Whether that's a good thing depends on context.
The trope carries rather different cultural baggage depending on which side of The Pond you live on.
- American crosswords are typically interlocking grids, with a theme for the lengthier answers, while the rest of the puzzle features vocabulary tests. An American doing a crossword is likely to be portrayed as being of slightly-above-average intelligence, especially if it's the New York Times crossword. (The crosswords featured in Harper's are Nintendo Hard, mostly because the clues are VERY obscurely worded and require a buttload of abstract thinking to decode.)
- British crosswords resemble snaking mazes with clues that require a working knowledge of mythology and literature, with cryptic clues layered with double meanings (non-cryptic crosswords are known as "quickie" crosswords). A character seen completing The Times or The Guardian crossword (or, in extreme cases, The Listener) will be very smart. In contrast, a character shown doing crosswords in The Sun will be ridiculed.
- One Jared commercial has the woman using a supposed crossword clue "what's a fourteen letter word for marriage proposal?" as a way of telling her mother that her fiancee went to Jared's.
- In Batman: Hush, the Riddler is seen to do a crossword puzzle without the clues. He seems to think it makes him look really intelligent, but it shows him for the fool he is--the clues are there to tell the player what to think of.
- In the movie Trapped in Paradise, a priest uses them to pass the time during confession.
- Played with in Hot Fuzz!. The landlady of the inn Nicholas is staying at is reading out the description of a strong-armed authoritarian form of government (or something to that effect) while he, a strong-armed authoritarian police officer, is making his way in. She realises the answer and he takes it the wrong way.
- The Coneheads movie had them confusing a crossword puzzle with their own language.
- In the movie The Strange Case of the End of Civilization as We Know It, descendants of Sherlock Holmes and Dr. Watson have a Hurricane of Puns version of the continually asking conversation:
Watson: 1 Across. A simple source of citrus fruit, 1, 5, 4.
Holmes: A lemon tree, my dear Watson.
Watson: 2 Down. Conservative pays ex-wife maintenance. 7, 4.
Holmes: Alimony...alimony Tory, my dear Watson.
- The documentary Wordplay revolves around the American Crossword Puzzle Tournament and the oddballs who compete in it; it also features interviews with celebrity crossword buffs like Jon Stewart, Bill Clinton, Bob Dole and Ken Burns.
- The Ocean's Eleven remake provides a subversion of 2. Bernie Mac's character fills in a crossword with details of an overheard conversation while in an employee breakroom. But he's not distracted, he's taking notes covertly for later nefarious deeds.
- In All About Steve, the heroine is a crossword compiler whose infatuation with a TV news cameraman leads to her expulsion from the newspaper office where she worked.
- Dan in Real Life takes place during an annual family reunion. The family has a tradition of a competition between the men and the women to fill out the newspaper crossword first. This is used as evidence of the eponymous protagonist's skill with words (since the family credits Dan as the reason the men usually win) and establishes the Love Interest as Dan's equal (since the women win with her there).
- In Sideways, Miles is seen working on the New York Times crossword a couple of times (actual published puzzles from 2003). A few reviews pointed out that he was filling them out in pen, a sign of his Insufferable Genius personality, but the actor later admitted that he just used what the prop department gave him, and didn't think there was that much meaning to it.
- In the Young Bond novel Double or Die, a kidnapped teacher/crossword compiler plants clues to his abduction in his final cryptic crossword.
- In the recent novels of the Discworld series, the Ankh-Morpork Times publishes British-style cryptic crosswords, which Lord Vetinari enjoys. As with many British crossword compilers, the Ankh-Morpork Times setter goes by an appropriate pseudonym, in this case simply "Puzzler". (The founder of this trend in Real Life was "Torquemada" of The Observer.)
- These types of crosswords are described by Internet humorist Lore Sjoberg as involving "anagrams, wordplay, and trafficking in the occult".
- Note that crossword puzzles in Discworld apparently predate the Ankh-Morpork Times, as Vimes compared the references Heralds work into coats-of-arms as "crossword clues" back in Feet of Clay.
- James P. Hogan's Giants' Star includes a cryptic crossword used to sneak information from Ganymede base to Earth.
- Characterization-by-crossword in "Swellhead", a short story by Kim Newman: Two of the characters have subscriptions to a high-end crossword magazine that "scorned newspaper distribution. The publishers set an entrance exam for the subscription list, charging on a sliding scale, lower price for higher grades." One character, who has a pretentious streak and an inflated opinion of himself, pays £1,000 a year for the privilege of being counted a subscriber. The other, to whom he considers himself superior, gets his for free.
- Isaac Asimov's YA mystery "The Key Word" hides the keyword for a cipher in the New York Times crossword.
- In "The Fascinating Problem of Uncle Meleager's Will", a Lord Peter Wimsey story by Dorothy L. Sayers, the eponymous uncle leaves behind an extremely arcane crossword puzzle that must be solved to obtain the inheritance. The puzzle itself is reproduced at the end of the story, for any readers who want to try and solve it themselves.
- Inspector Morse is a fan of cryptic crosswords. Several of his novels give a crossword clue early in the book, and reveal the answer in a later chapter.
- The third Harry Potter book would have been something of a drag if not for Sirius Black's fondness for crossword puzzles.
- Played with in the Doctor Who Eighth Doctor Adventures: Fitz is extremely good at crossword puzzles. He's probably cleverer than average, but not that brainy. His secret? He's an Artificial Human; for some reason, even though he wishes he'd got immortality for his trouble, he just developed a knack for crosswords and anagrams.
- In the Doctor Who Virgin New Adventures/Sherlock Holmes crossover novel All-Consuming Fire, the Third Doctor is doing the Times crossword in the Silent Room of the Diogenes Club (the crossword hasn't been invented yet, but he's got a newspaper from the future). The Seventh Doctor holds up a sign with one of the answers on it, causing Third to exclaim in annoyance and be ejected.
- The crossword mystery series by Nero Blanc is Uncle Meleager's Will in spades.
- The series The Puzzle Lady is about a crossword puzzle writer who solves murders.
- One Inspector Allhoff mystery story has a guest character mention that he's a crossword puzzle fan who reads a particular paper. Allhoff slips words from the previous day's puzzle into the conversation and when the man fails to react, correctly concludes that the visitor is a liar.
- The Dean Koontz's Frankenstein series contains Randal Six, an Artificial Human designed with autism who finds comfort in crosswords (imposing the order of letters in empty boxes soothes his anxiety). He escapes his cell by mentally turning the floor tile into crossword letters. When the tiles run out, he closes his eyes and draws crossword grids on the floor, and later learns that he can move freely for some reason when pushing a shopping cart.
- In American Psycho, Patrick Bateman fills in one crossword with "meat" and "bone", over and over again, because he's slipping.
- In Tinker Tailor Soldier Spy, Smiley spots a London Times crossword filled out completely, in ink, in the apartment of a psychologically disintegrating but still-sharp former operative.
- Michael Westen in Burn Notice sometimes receives messages from the mysterious organization that burned him in the form of crossword puzzles.
- Used comically in the Seinfeld episode "The Pez Dispenser". At the end, George asks Jerry, "What's a three-letter word for candy?" Jerry says, "Sorry, I don't know."
- On Fraggle Rock, Madame Trashheap was working on a crossword and needed a 12-letter word for life of the party. The answer, she claims, is her uncle Maximillian (spelt with a silent Q).
- A couple of game shows have been based on thematic crosswords:
- Jeopardy! regularly uses "Crossword Clues [letter]" as a category, where each clue is phrased as a crossword puzzle clue, and all five responses begin with the same letter.
- In Oliver's Travels, one of Oliver's friends is a crossword compiler who went into hiding after a run-in with the villain, and at one point Oliver finds a secret message in the crossword he's just completed that reveals the villain's identity.
- In one episode of M* A* S* H, Hawkeye accidentally caused a false alarm when his request for another character's help on a crossword puzzle was mistaken for a real distress call.
- Heroes uses a crossword to introduce Charlie's superpower of perfect memory. The sheriff struggling with the puzzle says he wants to shoot Will Shortz, perplexing the large fraction of the viewing public that doesn't know the name of the New York Times crossword editor.
- Leo McGarry on The West Wing reveals himself to be a fan of the New York Times crossword in the show's pilot when he complains about an inaccurate clue. In a different episode, President Bartlet asks his wife for help solving the day's puzzle while preparing for a social event. The puzzle mentioned in the show had previously run in the paper, and papers that syndicate the puzzle with a six-week delay ran it on the day the episode premiered.
- In an episode of Jonathan Creek, a psychic approaches a widow and tells her that her dead husband will answer five questions. Because her late husband had been good at crosswords, she demands that his ghost solve a clue from the day's crossword for her, and he does. Of course, con artists can be good at crosswords too...
- In a fifth-season episode of Angel, a doctor is shown asking his receptionist for a random clue for him to solve. This happens twice and he's unable to solve either of them, asking "give me another one". The doctor ends up being somewhere between incompetent and evil.
- Friends, paraphrased from memory:
- Stargate SG-1 features an episode where, after O'Neill downloads the entire Ancient database into his brain (again), has him filling in crossword spaces with what appears to be random gibberish but are actually terms in Ancient. Then again, he also answers the clue 'celestial body' with 'Uma Thurman'... But that's Jack O'Neill for you.
- An episode of Bottom begins with the main characters, deprived of the television which provides most of their usual entertainment, attempting to do a crossword. They are spectacularly bad at it; it's never revealed exactly what crossword they're doing, but since they're both exceptionally stupid it doesn't really matter anyway.
- Used in Supernatural. A girl Sam meets during his Ten-Minute Retirement is impressed with his ability to complete the New York Times puzzle.
- Albert Steptoe's contribution to the Parish Magazine.
- In an episode of Corner Gas, a Tarot card reader refers to the 18th letter of the alphabet and Wanda immediately says, "R!" Everyone looks at her strangely and she says, "I do thirty crosswords a day."
- The closing credit tag for one Community episode has Abed helping Troy with one. Oddly, all of the answers appear to be the names of the study group members.
- The very first episode of The Big Bang Theory has Leonard complete a crossword in a few seconds as an Establishing Character Moment (here).
- A sketch on The Two Ronnies featured a train compartment full of commuters working on their crosswords and being continually interrupted by Ronnie Corbett's character who was struggling with his (ridiculously easy) crossword. The final punchline involves him agreeing to shut up if Ronnie Barker's character helps him solve the final clue: "Found at the bottom of a bird cage; 4 letters; something, something, i, t". Barker tells him the answer is "grit". On hearing this, a nun seated in the compartment suddenly goes "Oh! Grit!" and hurriedly crosses out her own (unseen) answer.
- One Calvin and Hobbes strip featured Calvin attempting to solve a crossword puzzle. He was not very good at it. To paraphrase:
Calvin: A type of bird...I've got it! "Yellow-bellied sapsucker!"
Hobbes: But there are only five boxes.
Calvin: I know. These idiots make you write it real small.
- Blondie is often depicted doing a crossword while Dagwood watches television as they sit in the living room. (In recent years she's switched to Sudoku instead, probably as an example of Were Still Relevant Dammit.)
- A Sunday Strip of Moon Mullins had Kayo writing his own crossword. Lord Plushbottom commented that it must be very hard; Kayo said, "Nah, it's easy." Kayo showd LP the crossword with answers such as "RJHIEPOQ" and "VZK". Kayo said, "Making the crossword is easy. What's hard is writing the clues."
- FoxTrot has featured several that Jason composed for the sole purpose of insulting Paige.
- One song from Starting Here, Starting Now follows a woman filling out a crossword puzzle and pondering her recent break-up, since they always used to do the crossword together. It turns out that she always got the answers before he did, and he left her for a floozy who didn't threaten his intelligence.
- The Pandora Directive has one which gets you $100 the day after you send it in. You really need the money, too.
- Doing the crossword in The Sims 2 increases the sims' logic skill.
- In Sakura Wars V, Sabura finishes a puzzle, even though she was just asked to help with one clue, in order to show she was being the designated Jerkass in that part of the game.
- Lexi-Cross combined Wheel of Fortune with The Cross-Wits.
- Nothing Nice to Say featured a short appearance of a crossword puzzle where all the words are RoboCop.
- It's used similarly in Fans! to establish Hilda as a bona fide genius when she does the New York Times crossword. In pen. Strictly from the bottom up. While conducting a job interview. Because it helps her relax.
- The "Crossover" arc is set up as a crossword puzzle at the end, with dialogue-free frames as the black squares, and the first letter in each square with dialogue as part of the puzzle's solution. The arc deals with a crossword puzzle convention, and also deals with Hilda's recent PTSD regarding crosswords. (in a previous arc, Fedyg had kidnapped Hilda and tortured her by strapping a net to her face. The net resembled a crossword grid, so now thanks to Fedyg, she began to equate crossword puzzles with torture.)
- Also, T. Campbell is himself a crossword fan, and occasionally costructs crossword puzzles with clues taken from Fans.
- User Friendly now includes a relatively simple, geek-themed crossword every Sunday.
- An episode of Batman: The Animated Series uses crosswords for an interesting form of Shout-Out (do we have Signing Your Work or something like that?), where the words filled into the crossword are actually the names of writers and artists who worked on the episode.
- Something similar to the third variation: Rugrats featured one of the parents calling a crossword-puzzle help line, and we could see that the words he was filling in horizontally spelled "D-U-M-B" vertically.
- The Simpsons used the documentary Wordplay as the basis for an episode where Lisa becomes an expert cruciverbalist. Will Shortz and Merl Reagle have a cameo, and the Sunday puzzle featured in the episode ran in that Sunday's New York Times.
- In the Christmas Special "The Twelve Days of Christmas", a squire is charged with swiping the wishlist of the princess, so that a knight can present her with her heart's desire and win her love. But the squire accidentally swiped the answer sheet for the Royal Crossword Puzzle, and so the princess ends up receiving 1 partridge, 2 calling birds, 3 french hens, etc. The princess actually gets quite annoyed with the gifts, but her father asks her to let the squire keep bringing them because each gift gives him the answer for the crossword.
- Xiaolin Showdown
Jack Spicer: What's a four-letter word for "idiot"?
Jack Spicer: ...Perfect.
- In Jimmy Neutron, Sheen is shown to be doing a crossword puzzle in ink in the episode where his brainpower is increased. When Cindy points out that it's not that impressive since her dad does the same thing, Sheen reveals that the crossword puzzle is from the Beijing Times.
- In SpongeBob SquarePants, Mr. Krabs answers "money" in all five-letter word clues.
- A Tenchi Muyo! fanfic has one character working out a crossword to show her intelligence, playing the trope itself straight. (Japanese crossword puzzles being done in hiragana or katakana (phonetic writing), of course.)
- ↑ It's 'condottiere'
- ↑ He also plays guitar (and sings and writes his own songs) and speaks Chinese, but it never, ever, ever Looks Like A Job For Aquaman. Not that he's useless, of course, but he never gets much use out of his unusual skills. Other characters find his musical abilities impressive, but there's never a need for The Power of Rock.