- 2000: Monday: Now ... and Then (NYT (daily) Crossword 50th Anniv.) [.puz, .pdf]
- CSI: Crime Scene Investigation; 1.4 (TV series);
Catherine: "You're right, you know. I should be just like you. Alone in my hermetically-sealed condo watching Discovery on the big screen, working genius-level crossword puzzles, but no relationships. No chance any will slop over into a case."
Grissom: "Technically, it's a townhouse. And the crosswords are advanced, not genius. But you're right. I'm deficient in a lot of ways. But I never screw up one of my cases with personal stuff." 
2002: Steve's CrozzWord application debuts on Zaurus- Marathon (movie); "Each year, single New Yorker Gretchen (Sara Paul) tries to complete as many crossword puzzles as possible during a 24-hour marathon session while riding the subway. By performing this strange ritual (a legacy from her mother), Gretchen seems to be railing against the meaningless cacophany of city life. Though seemingly senseless, Gretchen's annual gesture speaks volumes about imposing personal order on the random dice throw that is daily life."
- A Star-Guarded Coronation (song) (video; 5:17) by Vintersorg, album Visions from the Spiral Generator; lyrics: "A star-guarded coronation / Over the crossword's profound and royal thrones"
- Happy at Last (song) (video; 2:49) by Josh Joplin, album The Future That Was; MayasMix @ 47:43
lyrics: "I'm not as smart as a Sunday Times crossword puzzle / Big words get me into trouble" - Hiccups (song) (video; 4:03) by Darren Hanlon, album Hiccups;
lyrics: "Some day without trying you'll find something that's rare / Like an eight letter word on a triple word square
A thousand ideas I try to tell crossword girl / How do I get one across when you're always too down?
And if things get hard will you throw in the pen? / But if you are unsure you can pencil it in" 
2003: Four Down And Twelve Across (song; 2:47) by George Strait, album Honkytonkville; MayasMix @ 35:58; lyrics: "Girl, this relationship we're in / To say the least it's puzzling' / Like a crossword puzzle / Fill in the blanks / [Chorus] What's four down and twelve across / Two letter synonym for lost That's me / And a three letter word / That rhymes with through / Oh I get it, that's you"- I Do My Crosswords in Pen (song) (video; 4:20) by On Broken Wings, album Some of Us May Never See the World; lyrics: "Ink bleeds deeper / When pressed hard / Soaks through paper and / Leaves stains on the table"
- 2004: Crossword Puzzle Blues (song) by Steve Mardon, album Critic's Darling;
lyrics: "All you offer me is cryptic clues...You came here on a Sunday, dressed in black and white / I'm just another fool /
Livin' with the crossword puzzle blues (break out the White Out) / Livin' with the crossword puzzle blues (where's my thesaurus)" - Word Wars (movie) "In this character-driven documentary, filmmakers Eric Chaikin and Julian Petrillo follow four 'word nerds' through their fastidious preparations and smaller tournaments that lead to the national championship Scrabble tournament in San Diego in 2002. Our favorite contender: Joel Sherman, a true dork with acid reflux trouble (he constantly quaffs Maalox) and no other discernable job besides playing Scrabble."
- 2005: Wordplay (song) (video; 3:08) (wikipedia) by Jason Mraz, album Mr. A–Z;
lyrics: "I am the wizard of ooh's and ah's and fa-la-la's / Yeah the Mister A to Z / They say I'm all about the wordplay" - Everyday (song) (video; 6:44) by Authority Zero, album Rhythm and Booze;
lyrics: "These masses of confrontation beating me down / I'm picking at the pieces to put them all back into place
A never ending crossword of questions collaborates / While asking myself, where are we going in time?" - Crossword (song) by Helen Slater, album Crossword; MayasMix @ 05:35
2006: WordPlay (movie): "WordPlay follows New York Times puzzle editor Will Shortz, his fans and contributors, and champion solvers at the American Crossword Puzzle Tournament, exposing the madness and mirth behind this not-so-puzzling national obsession."- Every Word (song) (video; 2:41) by Gary Louris (from WordPlay); MayasMix @ 94:08
lyrics: "You know every word is made up of letters / Made up of letters / Made up of letters" - Bananagrams (game)
- Simple Man (song) by John Corbett, album: John Corbett;
lyrics: "Crossword's on the table, coffee in the cup / She finds another word for waiting as he pulls into the drive ...
And she's working on that crossword, fightin' back a smile / Find another word for sober, let him sit out there a while" - Mozartian Crossword (classical) (video; 8:08) by Jiří Teml; MayasMix @ 11:50
- Crossword (song) (video; 3:41) by Bleak, album Burns Inside;
lyrics: "I couldn't solve her / God and our hearts cried / Together, as I let my air out / Like a crossword / Like a crossword / You are to me" 
2007: (Merv Griffin's) Crosswords (TV game show): IMdb- The Crossword Monologues (movie): "If people from different parts of the world lined up their monologues, as if in a crossword puzzle, these monologues would eventually create a conversation."
- Mariella (song) (video; 4:17) by Kate Nash, album Made of Bricks; MayasMix @ 85:30
lyrics: "Yes, she always got the crossword puzzle right everyday / And she could do the alphabet backwards / Without making any mistakes" - Crossword Puzzle (song) by Noro, album Love Sweet Dream; MayasMix @ 24:58
2008: The Simpsons: "Homer and Lisa Exchange Cross Words" (TV episode):
"Lisa discovers that she has a talent for solving crossword puzzles, and she enters a crossword tournament. Lisa's feelings are hurt when she discovers that Homer bet against her in the championship match... Crossword puzzle creators Merl Reagle and Will Shortz guest star as themselves."- Cross Words (movie): "On his 50th birthday, George, an arrogant, agoraphobic, crossword puzzle maker is mistaken for dead... and he must crash his own funeral to learn how to live."
- Burn Notice (TV series); "In the world of intelligence, if an operative hands you a crossword puzzle, chances are, you just received a coded message." ~Michael Westen
- Mon-Sun NYT Crosswords (songs; .mp3) by John Schnall; MayasMix @ 79:49
- 2009: Wordplay (TV game show)
- All About Steve (movie); "Convinced that a CCN cameraman is her true love, an eccentric crossword puzzler trails him as he travels all over the country, hoping to convince him that they belong together."
- Academia (song) (video; 3:16) by Sia from the TV movie Acceptance; MayasMix @ 64:00
lyrics: "You can be my alphabet...You're a cryptic crossword, a song I've never heard" - Little Bird (song) (video; 6:13) by Imogen Heap, album Ellipse; MayasMix @ 50:32
lyrics: "... little bird, little bird / What do you hear?... Crossword puzzles start to grate / One across Four letter word" - Crossword (song) (video; 2:38) by Deckchair Orange, album Deckchair Orange; MayasMix @ 21:53
- We Learned To Be Cool From You (song) (video; 6:50) by Jimmy Buffett, album Buffet Hotel;
lyrics: "Maybe I can parlez a little Francais / Maybe I can even write a whole page a day
Do a crossword puzzle in a minute or two / But I learned to be cool from you"