- The Artifact: The $200 offered by the bank every time one crosses Go. They were already offered in the original The Landlord's Game by Elizabeth Magie and were there to demonstrate the Georgist idea of the citizen's dividend, a form of basic income.
- Misaimed Fandom: Basically, anyone who misses the Aesop mentioned on the main page. Which includes the vast majority of players.
- Referenced by...:
- In the comic Folly and Innovation, some of the characters play a hybrid of Monopoly and Risk. 
- In the Red Dwarf novel Infinity Welcomes Careful Drivers, Lister wakes up on Mimas [one of the moons of Saturn] after a Monopoly pub crawl around London, which ultimately ends up in him joining the ship. Red Dwarf Magazine followed several groups of fans replicating the "Monopoly board pub crawl". None apparently ended up in a foreign country, though.
- Tim Moore wrote a travel book called Do Not Pass GO, involving a trip around London based on the board.
- Nick Carr went to Joisey in 2013 and took photos of how the Monopoly properties look today. In real life, these properties are quite unbalanced - North Carolina Avenue has the Resorts Casino, while Pennsylvania Avenue has...a bus depot.
- Jim Carrey makes a reference to Monopoly in Ace Ventura: When Nature Calls.
Ace: Ace Ventura: Pet Detective. And you must be the Monopoly guy...(leans in, whispering) Thanks for the free parking.
- In NetHack, it is (unsurprisingly) possible to die on the very first turn, without making a single move. If this happens, you are told "Do not pass go. Do not collect 200 zorkmids."
- Referenced in an episode of The Simpsons where oil is found under the school and Burns wants to buy it out.
Burns: I have a monopoly to maintain. I own the Electric Company and the Water Works. Plus the hotel on Baltic Avenue!Skinner: That hotel is a dump and your monopoly is pathetic.
- The Simpson family also owns several variant Monopoly boards, including "Edna Krabappelly". Their attempt to play ends in domestic violence.
- Also, in an early episode when Homer saves the plant from a meltdown, Bart plays Monopoly with Maggie in which he draws cards until he finds a "second place beauty contest" card.
- One city hall meeting scene sees Uncle Pennybags sitting right next to Mr. Burns. But he soon bails, saying he's late for a ride on the Short Line [railroad].
- In Snoopy, Come Home, Charlie Brown, Lucy, Schroeder and Linus play Monopoly. Lucy taunts Charlie Brown because she has both Boardwalk and Park Place; Chuck ends up landing on 'Go to Jail'. Lucy then lands on one of Schroeder's Green properties—specifically, Pacific Avenue—with hotels, no less. (The rent Schroeder asks, $1275, is accurate to a hotel on Pacific.)
- Tom Lehrer gets in on it, too, in "We Will All Go Together When We Go":
You will all report directly to your respective ValhallasGo directly, do not pass "Go", do not collect 200 dollahs...
- Death of the Discworld has reported playing something called 'Exclusive Possession' in lieu of the traditional chess game. He was the boot.
- In the Over the Hedge movie, everyone argues about the iconic tokens as RJ plans out the raid, and who gets to be the car. He sets the record straight: "I'm the car! I'm always the car."
- At the beginning of the Small Wonder episode "Haunted House", an electrical outage interrupts the Lawsons' Monopoly game.
- Zombieland has a scene where the main characters play Monopoly with actual U.S. dollars. (Not that they're worth all that much now...)
- The Forbes Museum in New York houses all of Malcolm Forbes' eclectic collections, including dozens of Monopoly variants and first print editions. It also includes a special one, printed for his birthday, where all the tiles on the board correspond to the actual companies and properties he owned.
- In Spin City, one of a series of questions Carter asks to see how well Stuart knows him is which playing piece he always uses in Monopoly (it's the shoe).
- Real Life: The boardwalk in Atlantic City has signs shaped like the various spaces which indicate where some of the streets are. There is also a fair amount of information about Monopoly in the Atlantic City History Museum, at the north end of the boardwalk.
- Calvin and Hobbes had them playing it in several strips, but with their own Calvinball-like rules. For example, Calvin once robbed the bank, causing Hobbes to dump all 12 hotels on Baltic Avenue. Another time, we find out that they write their own cards for the game. Hobbes launches a massive online scam on the bank ("I think I'll buy a few dozen hotels"), and Calvin vows revenge once he lands on Chance. God only knows what horrors the other cards hold. Viral contagions? Meteor strikes?
- In the Gumby short "Kid Brother Kids", two of the cowboys at the ice cream salon are shown playing Monopoly just before Gumby and his band start their concert.
- In the Cheers episode "The Art of the Steal," Norm brings a copy of the game to the bar to teach Woody about economics, and it shows general elements in playing the game, such as:
- Choosing who plays what (Frasier gets the racecar because he can imitate the car the best, while Cliff gets the thimble with no argument),
- Properties (Woody buys a railroad, then puts a house on it),
- And lost pieces (Norm is the lead pipe from Clue, there are pieces from Candy Land and a Chinese Checker, and they use a giant pair of dice).
- Ozy and Millie: Avery plays Monopoly to win. Timulty just enjoys reminding everyone that he's playing as the hat.
- Comedian Dane Cook has a few Monopoly-related jokes.
"Fuck this game! It's four in the morning, grandma; YOU WIN! I'm sitting on Baltic with crap! And where did you get the pink fifties, you cheating whore? Don't touch me, grandpa, nana is a CHEATING WHORE! And I should cut your head off with this little doggy!"
- Growing up the youngest of seven children, he got last pick of the Monopoly pieces. Since his parents were also playing, and there are only 8 pieces, he would use the knife from Clue.
- He also notes that almost every Monopoly game anyone plays usually ends like this:
- According to Dinosaur Comics, Monopoly is how the universe punishes truly awful mistakes. Its object is "to fully explore the sensations of boredom, sorrow and rage." Everyone wins. (Unless you're the actual winner, in which case "your prize is watching friendships die, turn by endless turn.")
- Jethro Tull's "Thick as a Brick":
We'll make a man of him
Put him to trade
Teach him to play Monopoly
And to sing in the rain
- In the That '70s Show episode "Cat Fight Club", the characters play Monopoly. Jackie is winning, and she happily notes that it's just like real life - she's the richest.
- In Irregular Webcomic!, it's joked that Monopoly is actually a weapon for the (somewhat inept) Martian invasion, intended to disrupt friendships and waste time. In the annotations for the same strip, the creator launches into a uncharacteristically vitriolic rant about the game, expressing a deep, deep hatred for it and disbelief that something that spits in the face of good gaming design still makes so much money.
- The title character in Arthur Christmas buys a Christmas-themed variant of the game as a gift for his quarrelsome family. They don't manage to play it too well, since Arthur's dad (Santa Claus), grandfather (retired Santa), and older brother (heir apparent to the Santa post) all fight over who gets to be the Santa piece.
- Played in universe in Only Fools and Horses. Some jokes include Del owning everything on the board, Rodney getting annoyed and throwing the board off the table and Grandad saying he doesn't want to stay in a hotel next to a waterworks and isn't paying.
- In The Brady Bunch episode where all six kids get the measles, there's a scene where four of them are playing Monopoly.
- Some major retailers or restaurants (most notably McDonald's) run annual Monopoly themed promotions, based around collecting pieces to form monopolies for a prize.
- In Friday the 13th (1980), Brenda, Bill and Alice play "Strip" Monopoly.
- The Young Ones were quite fond of Monopoly, up to a point:
- In "Boring", Vyvyan became bored with the usual rules and edited the cards to create his own house rules, including "You have won second prize in a beauty contest. Smash Rick over the head with the bank," "Congratulations! It is your birthday. You may set fire to Rick's bed," and "Get out of jail free: You may keep this card, sell it, or stick it up Rick's bottom."
- Vyv was also frustrated by Neil's attempt to nail some plates to the table in "Cash" because "What happens when we want to play Monopoly? Go directly to plate? Do not pass plate nailed to the table by a stupid hippie?"
- In the Poirot episode "The Lost Mine", Hercule Poirot and Captain Hastings play Monopoly from the beginning of the episode, and this becomes a Running Gag throughout said episode. Eventually, Poirot learns that playing the game could be the clue to solving the mystery of who killed Han Wu Ling.
- The game "Monotony" is in Ren and Stimpy's board game collection.
- In FoxTrot, Jason has an unusual strategy for winning — keep shaking the dice (and calling for doubles) until all the other players give up and quit.
- Trope Namer: This board game has named the following tropes:
- Keep Circulating the Tapes: All 12 episodes circulate, but haven't been rerun.
- Missing Episode: A 13th episode was planned but apparently not even taped. Instead, ABC debuted America's Funniest People after the success of its aired pilot on May 1.
- Old Shame: The second unaired pilot featured Patty Maloney playing the part of Uncle Pennybags and basically being a living token for the contestants to move. The aired episodes replaced her with lights on the board.
- One-Book Author: For Reilly.
- What Could Have Been: Marc Summers and Peter Tomarken are two well-respected emcees, and they were in 1990. The fact that Merv Griffin decided to go off the board with Mike Reilly when the show finally went to series, especially since Tomarken wasn't really doing much of anything, may say a lot about Merv.
- The game has numerous ticker messages, among them being:
- “The ELECTRIC COMPANY keeps the Bank safe from Safe Crackers”
- “Become Lost in a Zone – Play Pinball.”
- “Game tip – collect all property to play LAND GRAB”
- “NASDAQ +230 DOW JONES +410 … We Wish”
- “Never Panic”
- “A Jackpot a day keeps boredom away”
- “Hey, it’s only Pinball”
- “The future of Solar Electricity is Bright”
- “This sign is fun to watch”
- “Did you know famous people play MONOPOLY?”
- “Take a Chance – Play MONOPOLY”
- “Boardwalk, Park Place … Not just for rich folks”
- “The ball is always wild”note
- “How many messages does this sign have, anyway?”
- “Electric Company reports POWER ON in game”
- "Make new friends... then beat them by playing Monopoly"