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“Mr Monopoly” Caption Contest Commentary with Lawrence Wood

April 7, 2025 by Lawrence Wood

CartoonStock caption contest cartoon by Kyle Bravo. Mr monoply man is sitting in an armchair while an angry woman stands over him with her arms on her hips

Bob Mankoff was unable to join the judging panel this month because he was not feeling well, and we all wish him a speedy and complete recovery. 

New Yorker cartoonist Kyle Bravo submitted the drawing for this month’s contest, which features Mr. Monopoly, the mascot of the board game Monopoly. He’s in his living room, relaxing in a recliner, holding the remote control for his TV, and addressing his wife, who’s standing with her hands on her hips. 

Bravo was reluctant to let us reveal his original caption, but here it is: “You knew I was Mr. Monopoly when you married me.” A couple of you submitted jokes with a similar structure: 

  • “You knew I was a player when you married me.”
  • You knew my money was fake when you married me.”

That second entry is good, but here’s an even better version: “I never said it was real money.” And here’s one that’s just OK: “It hurts when you say I’ve never made any real money.”

Here are the month’s best puns:

  • “You used to love my monopolizing things.”
  • “Here come the water works.”
  • “This is my park place.”

Here’s the best long caption: “What happened to the two 500 dollar, two 100 dollar, two 50 dollar, six 20 dollar, five 10 dollar, five 5 dollar, and five 1 dollar bills I just gave you?” (It would be better, however, if the word dollar were replaced with a dollar sign: “What happened to the two $500, two $100, two $50, six $20, five $10, five $5, and five $1 bills I just gave you?”).

And here’s the best scatological joke: “That wasn’t Go I just passed.” Bravo yelled “NO!” when he saw that entry, but God help me, I like it. Yes, it’s vulgar and juvenile, but it does a nice job of combining a reference to the game with a comment on men who spend too much time in their La-Z-Boy recliners, and it made me laugh out loud. It still does. 

Many of you suggested that the couple are having a heated argument:

  • “You know what it’s like when the bottom falls out.”
  • “Go to hell. Go directly to hell.”
  • “Go directly to hell.”
  • “You shave yours first.”

I especially like that last entry, even though it is sexist and mean, because it was the only one to allude to Mr. Monopoly’s mustache. 

Like the “water works” and “go directly” entries noted above, the next several captions allude to cards that are used in Monopoly: 

  • “Yeah? Well, it’s also been a while since you won second prize in a beauty contest.”
  • “I don’t think you understand what a compliment ‘second prize’ is.”
  • “Second place is in a beauty contest isn’t much to brag about.”
  • “There is no ‘Take Out the Trash’ card.”
  • “I’m using my ‘Get Out of Housework Free’ card.”
  • “Advance to Kitchen. Collect Snack and Beverage.”
  • “Can you advance to the kitchen and collect me a beer?”

And this entry alludes to one of the game pieces: “I suggest you get a hotel.”

This caption cleverly suggests that both Monopoly and some bad marriages seem endless: “This has gone on far too long and isn’t fun anymore.” This caption makes the same point about the game but doesn’t tie it to bad relationships: “The game will be over in 11 hours.”

I like this caption, but it buries the punchline: “When I was in jail, you never visited me once.” A better version would be, “You never visited me in jail.”

Here’s a nice reference to the way players win the right to purchase properties in Monopoly: “I landed on it first.”

And this refers to the way they move around the board: “You’re blocking the TV, go back 3 spaces.”

This caption incorporates a reference to the domestic scene in Bravo’s drawing: “Did you launder my money?”

And finally, we have a reference to just how boring watching TV can be: “I’m also into monotony.

Congratulations to frequent finalist MARK STROUT, who submitted the winning caption: “I landed on it first.” 

The five runners-up are:

  • “I don’t think you understand what a compliment ‘second prize’ is.”
  • “This has gone on far too long and isn’t fun anymore.”
  • “Advance to Kitchen. Collect Snack and Beverage.”
  • “You used to love my monopolizing things.”
  • “I never said it was real money.”

Watch the Judging Process

If you want to see how we made our selections, we recorded the process with Kyle and you can watch that below

Like what you see? Subscribe to our YouTube channel for more Caption Contest episodes.

We’re just a couple months away the one-year anniversary of the publication of my book on the The New Yorker Cartoon Caption Contest. I promise to stop promoting my book after the anniversary passes on June 4, but until then I’ll continue urging you all to buy as many copies as possible. 

Related posts:

"Bird and Squirrel" Caption Contest Commentary with Lawrence Wood

"Grandma and the Wolf" Caption Contest Commentary with Lawrence Wood

"Runner's High" Caption Contest Commentary with Lawrence Wood

"Mood Music" Caption Contest Commentary with Lawrence Wood

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