Boggles the Mind

"Ashley: "You have to stop thinking about Lisa."

Will: "I am not thinking about Lisa. D-U-M-P-E-D. Dumped."

Ashley: "Right. And before that you had Sad. Lonely. And Pathetic."

Carlton: "No Ashley, that's me. I'm Pathetic.""

- Fresh Prince of Bel Air

In Real Life, people playing Scrabble generally try to play the highest-scoring word they can, or failing that, any word they can find. Even if it's not, strictly speaking, real. The opportunity to put down meaningful words is sharply limited by the random letter draws that occasionally leave players with nothing but consonants, or four E's, or similarly useless combinations, and even if you can form a relevant word, there still might not be a place on the board where it can go. Still, it's fun if you can pull it off.

In fiction, however, Scrabble tiles are magic Rorschach's Ink Blot style windows to the soul. If we see characters playing a word game, then either the word being played, the only word the character can make, or every word on the board will somehow relate to things that are on their mind. Alternatively the words will Foreshadow events they are unaware of. The game in question will usually be Scrabble, but not necessarily - other games that can be used include crosswords, anagrams, Countdown, or any other word game.

Name is, of course, a pun on the board game Boggle.

Film

 * In Alfred Hitchcock's Suspicion, the characters are playing "anagrams" when Lina notices that Johnny's tiles spell out "murder."
 * Not exactly this but in Sneakers the characters give up on their game of Scrabble and start using the tiles to work out anagrams of Setec Astronomy. After a couple of funny misfires (including Cooty's Rat Semen) they arrive at 'Too Many Secrets'.
 * In the movie Foul Play, the old ladies are playing Scrabble when we see that all their words are "dirty".

Literature

 * Invoked by Arthur in The Restaurant At The End Of The Universe, when he uses random drawing from a scrabble bag to try to reveal the Ultimate Question in his subconscious.
 * Played with in the Doctor Who New Adventures novel Conundrum, in which the Doctor and another character play a game of Scrabble in which every word is significant--and the Doctor immediately points to this as a sign that their actions are being controlled by an outside force. Especially when his opponent makes an impossible move and the Doctor points out the continuity error.
 * Patrick Bateman fills in a crossword with some rather... sketchy answers in American Psycho. Of course, with the Unreliable Narrator and frequent hallucinations it's entirely possible they were the right answers, or at least that he thought they were.

Live Action TV
"Guard: Three letters; to walk quickly, manage or oversee.
 * Lampshaded on Father Ted; He rages that his arch-nemesis Dick Byrne must have cheated when he spelt out "useless, priest, cant, say, mass".''
 * Also evidencing a clever bit of Loophole Abuse in substituting the real word "cant" for the illegal abbreviation "can't". But that might be overthinking the joke...
 * Done in Skins, where the recovering anorexic Cassie and one of her loony bin mates are playing and the whole board is covered in foods.
 * In the Spaced episode "Epiphanies", when Tim and Daisy get into a Scrabble-tile-throwing fight after an argument over whether "Shazam" or "Pro-V" counted as words, Daisy notices that the last 4 tiles they threw at each other spelt "Fuck". Tim asks her what she thinks that means, hinting at the couple's UST.
 * A crossword semi-example from another episode;

[alarm sounds]

Mike: Run!"

"Ted: 'Husband'
 * An episode of Benson had Death taking part in a game of Trivial Pursuit. Every question he got had some relation to death -- the name of Jerry Garcia's band, for instance. Benson accused him of cheating, but he denied it, saying, "You've heard it said, 'He cheated Death," but no one has ever said, 'Death cheated him!'"
 * One episode of Stargate SG-1 had O'Neill doing a crossword after downloading the Ancient database into his head (again) as he waits for his subconcious to gain access to the knowledge, including where the MacGuffin they need is. Dr Jackson notices he's been unconciously filling in answers in Ancient, and theorises that these are clues to where they need to go (he's right). Carter remains skeptical because he also filled in 'celestial body' as 'Uma Therman'.
 * Invoked by Ted in How I Met Your Mother, trying to broach the subject of whether Robin has ever been married.

Robin: There's no 'P' in 'husband'

Ted: Hmm... you seem to know a lot about husbands..."

Web Comics

 * This strip of Albion Fuzz
 * According to this strip of Xkcd, whenever the author plays Scrabble with his girlfriend's mother, he always gets the letters for words like "Clitoris."

Western Animation

 * Peggy Hill does this with Boggle in King of the Hill ("Sad", "Bad", "Man", "Abandoned", "Abandons"...)
 * The Simpsons episode "The Bart Wants What It Wants": Bart became friends with a girl; all her words on the grid were love-related. We then see Bart put down the word "Oblivious".
 * There was another one in the episode where Maude Flanders died: Ned plays a game against himself, with all the words being about loneliness. And "horny".
 * Family Guy had Stewie subconsciously spelling "My darling Janet" with alphabet blocks. When he realizes what he's done, he knocks over the blocks, causing them to spell "I long for you." He knocks them over again, spelling "Ride that pony."

Real Life

 * At the US Space and Rocket Center in Alabama, there's a restored trailer where lunar astronauts were quarantined, complete with a vintage Scrabble board. The restoration people had some fun and spelled out "Lander", "Rover" and "NASA" in the tiles on the board.