- In an Ed, Edd n Eddy comic book story, the titular Eds play a parody of Dungeons & Dragons. When the game begins, Ed says "Do not pass go. Do not collect $200".
- In Adventures of Superman (1987) Issue #59, an officer tells Brainiac "Do not pass go... do not collect two hundred dollars... go to jail. Go directly to Jail!".
- A back-up strip in Justice League America Annual #8 had the League having a quiet day (unaware that a supervillain team began a plan to destroy them but descended into chaos). At one point they're shown playing Monopoly, with Booster Gold insisting "I didn't stay in the hotel, I flew over it!"
- Off the Mark:
- "How come you always get to be the top hat?"
- "Sorry. When you said 'Boardwalk', that second syllable got me involuntarily excited."
- "They expect him to be a game changer..."
- "I'd drop in more often, but I can't afford it."
- "Well, I'll be... It's a 'Get Out of Time-Out Free' card..."
- "When you pass 'Stop', we collect $200."
- Two men go hunting for the biggest game of all..
- "Ooooo! Looks like you landed on Park Place... and I just put two hotels there!"
- A Running Gag in Sally Forth (Howard) is the family playing Monopoly and Ted coming up with increasingly outlandish House Rules until what they're playing isn't really Monopoly any more.
- 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 computer scam on the bank ("I think I'll buy a few dozen hotels"), and Calvin vows revenge once he lands on Chance.
- 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.
Film - Animated
- 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.
- In Over the Hedge, 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."
- 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.)
Film - Live Action
- Ace Ventura encounters a man who looks like Uncle Pennybags 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 Friday the 13th (1980), Brenda, Bill and Alice play "Strip" Monopoly.
- Zombieland has a scene where the main characters play Monopoly with actual U.S. dollars. (Not that they're worth all that much now...)
- Tim Moore wrote a travel book called Do Not Pass GO, involving a trip around London based on the board.
- 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.
- In Reaper Man, Death mentions having played something called 'Exclusive Possession' in lieu of the traditional chess game. He was the boot.
- The short story "War Game" by Philip K. Dick features a Monopoly-like board game called Syndrome that is designed to mentally undermine the youth of a planet in the lead-up to an invasion. In what may be a reference to the way nobody ever plays Monopoly by the actual rules, the customs team tasked with inspecting the game to make sure it's safe to import fail to notice the psychological warfare aspects of the rules because they just glance over the rule sheet and go "Oh, it's just like Monopoly".
- A Darkness More Than Night: Terry McCaleb tells Harry Bosch that, to the bureau's civil rights division, nailing down an LAPD cop is more valuable than Park Place and Boardwalk together.
Live Action TV
- In The Brady Bunch episode where all six kids get the measles, there's a scene where four of them are playing Monopoly.
- 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, as though they're on High Rollers).
- In the Only Fools and Horses episode "Friday the 14th", the Trotters stay at a creepy-looking cottage in Cornwall, where Rodney finds a Monopoly board (Del: "Monopoly?! Now we are all doomed!") They end up playing and of course Del owns nearly everything on the board. The game ends abruptly when Grandad quibbles about having to pay £1200 to stay in a hotel next to a waterworks and Rodney tosses the board up in frustration.
- In the Poirot episode "The Lost Mine", Poirot and Hastings play Monopoly from the beginning of the episode, and this becomes a Running Gag throughout. Eventually, Poirot learns that playing the game could be the clue to solving the mystery of who killed Han Wu Ling.
- In Porridge, Fletcher is in the midst of a long-running Monopoly game against Blanco. Barrowclough remarks that they are "cheating each other into a stalemate."Fletcher: (picks up a Chance card) Would you Adam and Eve it?! Go to jail!
- In "The Last Date", Roseanne and Dan Connor try to rekindle their social life, as the alternative is staying home and playing Monopoly with Dan's sister-in-law. Later, Jackie's seen playing the Monopoly game with herself.Dan: If there's a lonely, pathetic, yet bizarrely-chipper woman standing in our kitchen with a Monopoly game, it must be Saturday Night.
Jackie: Maybe that's what life looks like when you're stuck on Baltic Avenue, but on the Green properties, life is sweet.
- At the beginning of the Small Wonder episode "Haunted House", an electrical outage interrupts the Lawsons' Monopoly game.
- A drunken game of Monopoly in The Sopranos turns nasty, resulting in a fight between Tony and Bobby.Janice: Second prize in a beauty contest. Collect $10. Go ahead, make your stupid joke.Tony: I got nothing to say.Bobby: Think I'll buy a railroad.Tony: A German shepherd's shaved asshole won first prize.Bobby: Oh! You're talkin' about my wife!Tony: You married her.Bobby: It's my home. No more talkin' like that.Janice: It's OK, Bobby.Bobby: Stay outta this! You Sopranos. You go too far.Tony: Alright, you know, Jan, he's right. I'm sorry. I crossed the line. I apologize. Won't happen again. [begins softly singing] Under the Boardwalk. With a schlong in Jan's mouth. Under the...[Bobby punches him]
- 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).
- 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. And Fez flips over the board.
- 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?"
- An Evening Wasted with Tom Lehrer, "We Will All Go Together When We Go":You will all report directly to your respective Valhallas
Go directly, do not pass "Go", do not collect 200 dollahs...
- 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
Stand Up Comedy
- Comedian Dane Cook has a few Monopoly-related jokes.
- 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:"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!"
- Victoria Wood, in a routine where she describes spending Christmas at a friend's house, says never play Monopoly with people who've been playing together every Christmas for years, because everything you do is wrong.
- 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."
- 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.")
- In Folly and Innovation, some of the characters play a hybrid of Monopoly and Risk. 
- 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.
- Ozy and Millie: Avery plays Monopoly to win. Timulty just enjoys reminding everyone that he's playing as the hat.
- 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.
- In the Zero Punctuation review of Velvet Assassin, Yahtzee says that the only real purpose for Violette's Morphine Mode is allowing her to swiftly delete one inconveniently alerted Nazi, and calls it "a one-time Get Out of Fuck-Up Free card" (a parody of the board game's "Get Out of Jail Free" card).
- In Cracked's list of the "5 Terrible Excuses for Homophobia (That People Keep Using)", #3 is the "I misspoke" excuse, which "becomes the Get Out Of Homophobia Accusations Free card".
- In "The Ballad of Buster Baxter", Arthur, Brain, and Buster attempt to play three-player checkers. Buster is forced to play with various small items since there are not enough pieces, one of which is the boot token, which Arthur refers to as a "Monopoly shoe". The trio eventually gives up on trying to add a third player and Buster sits out.
- In "The Frensky Family Fiasco", Francine organizes a family night with "Megalopolis" and calls dibs on being banker. Her older sister Catherine scoffs, "That was already old when I was 8." The game functions identically to the real thing, except that houses, hotels, railroads, and Community Chest were swapped respectively for condos, skyscrapers, shipping lines, and "Pot of Gold". An argument ensues when Catherine accuses Francine of giving herself an extra $20 when making change, which sparks a separate argument between their parents when the father inadvertently reveals he had been hiding money in his pocket. The chaos culminates with the family cat noticing a mouse-shaped token and pouncing at it on the table.
- 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 Ren & Stimpy Show, the game "Monotony" is in Ren and Stimpy's board game collection.
- Phineas and Ferb:
- In the Made-for-TV Movie, characters living under the repressive dictatorship of Doof-2 play "Doofopoly".
- "Skiddley Whiffers": The titular board game plays like a hybrid of this and Mouse Trap.
- "Night of the Living Pharmacists:" According to her dad, Vanessa's favorite board game as a kid was called "Kleptocracy".
- Robot Chicken:
- A sketch from "Cannot Be Erased, So Sorry" has a prison inmate ask the shoe, dog, thimble, and car what they're in prison for.
- A sketch from "Butchered in Burbank" features a sneak peak at the HBO original series, Boardwalk Monopoly.
- A sketch from "Zero Vegetables" is entitled "50 Shades of 'Bags", where Uncle Pennybags engages in intercourse with Anastasia Steele.
- A sketch from "Why is it Wet?" has Uncle Pennybags firing the thimble and replacing it with a pile of smiling feces. After a brief unsuccessful career as a prostitute, Thimble joins a knitting club, having mistaken it for Losers Anonymous.
- The Simpsons:
- Referenced in an episode 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 owns several variant Monopoly boards, including "Edna Krabappelly". Their attempt to play ends in domestic violence.
- 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 the "you won second prize in a 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].
- Referenced in an episode where oil is found under the school and Burns wants to buy it out.
- 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.
- 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.
- Some major retailers or restaurants (most notably McDonald's) run annual Monopoly themed promotions, based around collecting pieces to form monopolies for a prize.