Can You Guess the Meanings of These Old-Timey Phrases?

By: J. Reinoehl
Estimated Completion Time
4 min
Can You Guess the Meanings of These Old-Timey Phrases?
Image: shutterstock

About This Quiz

Calling all etymology lovers! Slip me some skin before we go on this idiom adventure! Do you know or remember what “fat city” means? How about the term “nosebleed?” What does saying that you’re a monkey’s uncle mean? Think you know the answer to these questions? Even if you don’t we hope this quiz gives you a blast from the past. It’s no skin off our teeth if you learn something, too!

Just to set the record straight, we know slang changes over time. That’s why this quiz focuses on slang from yesteryear. Some slang, like “nerd,” has continued into our vocabulary today (single-minded expert in a technology field). Other phrases, like “jacked up,” used to mean one thing (a raised car) and now mean something very different (not working as intended; or high on drugs or drunk). And other phrases like “flutter bum” have faded into oblivion (handsome guy).

There are plenty of slang phrases here to test your knowledge so put the pedal to the metal and burn rubber. This “Can You Guess the Meanings of These Old-Timey Phrases?” quiz is here to discover what you know about the slang of the past.  Don’t be a party pooper! Take this quiz and then challenge your friends to beat your score!

What does “put an egg in your shoe and beat it” mean?
You have horrible fashion sense
You’re an idiot
You’re an awful cook
Get out of here
Correct Answer
Wrong Answer

“Put an egg in your shoe and beat it; make like a tree and leave; imitate an amoeba and split.” –Stephen King from Needful Things

What is a “duck butt?”
A type of shoe
A type of car
A type of hairdo
A type of food served on Thanksgiving.
Correct Answer
Wrong Answer

Sometimes called the ducktail (or more offensive terms), this hairstyle screams 1950’s. Worn by non-conformists like Danny Zuko in Grease, the hairstyle required a log of hair grease and a rattail comb.

What does “fake out” mean?
Sealed exit
Bad movie
Poorly constructed bridge
Correct Answer
Wrong Answer

“It’s a mental fake-out to myself. I make believe I’m making a new show, so I forget the material I was working on and make up some fresh material.” –Eric Bogosian


What does “fat city” mean?
A city known for its obese population
A group of beautiful women
Living comfortably
The garbage bin
Correct Answer
Wrong Answer

The term originated in the 1960’s. Ironically, Manteca, California could be considered the literal “Fat City” since Manteca means “lard” in Spanish.

Which of the following means “crazy”?
“Rain napper”
Correct Answer
Wrong Answer

“They’re creepy, and they’re kookie, mysterious, and spooky. They’re all together ooky, the Addam’s Family.” –Vic Mizzy from the opening lyrics of the Addam’s Family.

What are “threads?”
Chain letters
Correct Answer
Wrong Answer

“Threads” became the slang for clothing in the 1920s. The word comes from an Old English word that means “twisted, fine cord.”


What does “my keepers” mean?
Correct Answer
Wrong Answer

“Ah, children, pity level-crossing keepers, pity lock keepers, pity lighthouse keepers, pity all the keepers of this world (pity even school teachers) caught between their conscience and the bleak horizon.” –Graham Swift

What is a “drag?”
An event where horses pull stumps out of the ground
A boring person or event
Sipping coffee
A handbag
Correct Answer
Wrong Answer

“Drag” has many meanings throughout the decades. A drag race is a short straight-line race between two vehicles. People can also take a drag (inhale) from a cigarette.

What does “binoculars” mean?
Good eyes
Large ears
Correct Answer
Wrong Answer

“I got binoculars ‘cause I don’t want to go that close.” –Mitch Hedberg


Which of the following means you achieved your goal quickly?
“In like Bob”
“In like Flynn”
“In like Gandhi”
“In like Mike”
Correct Answer
Wrong Answer

This phrase began in the 1940’s and was a reference to the actor Errol Flynn. Flynn was said to be a womanizer, accused of raping several underage girls, and after his death, his home was found to be filled with peepholes and two-way mirrors.

What does “noggin’” mean?
Brain or head
A sled or sleigh
Going bar hopping
Hanging out at the drive-in
Correct Answer
Wrong Answer

“We’ll look at you. You get a bump on the noggin, and you think you’re Pancho Villa.” –John Spartan in Demolition Man

What does “nosebleed” mean?
Annoying sibling
A charismatic person
A straw
Correct Answer
Wrong Answer

Nosebleed is another word that has several slang definitions. Currently, “nosebleed seats” are those stadium seats at the highest and furthest point from the screen, stage, or playing field.


Which of the following slang terms is something used to "address someone?”
Correct Answer
Wrong Answer

“Come on, Mia. Let’s go get a steak.” “You can get a steak here, Daddy-O.” –Vincent and Mia in Pulp Fiction

What does “living the life of Riley” mean?
A sheltered life
A sad life
A turbulent life
A life of luxury
Correct Answer
Wrong Answer

“The life of Riley” is traced back to World War I. The Riley referred to in the phrase has been traced all the way back to a ballad of the 1820’s about Willy Reilly who ran away with an heiress.

What does "jalopy” mean?
An old beat-up car
A hot dog
A hairstyle
Correct Answer
Wrong Answer

“Now instead of loading up your jalopy and heading for California, you take a second badly paid job. ‘The Grapes of Wrath’ has turned into ‘Nickel and Dimed.’” –Geoff Dyer


What does “backseat bingo” mean?
Finding coins in the seat cracks
A dog that loves riding in the back with its head out the window
Being carsick
Kissing in the back of a car
Correct Answer
Wrong Answer

Backseat bingo was once a way of making out. Now, it is a brand of board games that have sliding panels and that people on trips can play in the car.

Which of the following is not old-time slang for something “boring?”
Mickey Mouse
A square
Madison Avenue
A pill
Correct Answer
Wrong Answer

“I think what democracy means today, in reality, is to a large extent manipulated consent—not forced consent, manipulated consent—and manipulated more and more with the help of Madison Avenue [advertising].” –Erich Fromm

What does the phrase “not for all the tea in China” mean?
Not at any price
It is going to be a difficult endeavor
That was funny
It is popular
Correct Answer
Wrong Answer

China currently makes ¼ of the world’s tea and has historically been the world’s largest producer. The phrase is said to have originated around the 1900s in Australia.


What does it mean if you say, “I’ll be a monkey’s uncle?”
You love animals more than you love children
You aren’t very smart
You are disappointed in your nephew
You are surprised
Correct Answer
Wrong Answer

“If that’s a joke, I’m a monkey’s uncle.” –From the Chronicle-Telegram (Elyria, Ohio) February 8, 1925 (the year of the Scopes trial and first year this phrase appeared in print)

What does “knee high to a grasshopper” mean?
You aren’t very smart
Very young
You keep your grass too short
A type of short socks
Correct Answer
Wrong Answer

The largest insect in the grasshopper Order, Orthoptera, is the wētāpunga (weta). The largest recorded weta was 4-1/3 inches long and had a leg-span of 7 inches.

What does “jerking my chain” mean?
Harassing me
To carry someone else’s weight
To hurry up
To break my necklace
Correct Answer
Wrong Answer

“How do you keep people from jerking your chain? Don’t give your chain to jerks.” –Bill Crawford


What does “at sixes and sevens” mean?
You’re lucky
You’re young
You’re confused
The weekend
Correct Answer
Wrong Answer

In the 1300s, “To set on six and seven” meant to risk a fortune carelessly. How it eventually became a phrase that means confusion is at sixes and sevens itself.

What does “Nowheresville” mean?
A town where all the excitement is
A boring or obscure town
A crime hub
A ghost town
Correct Answer
Wrong Answer

BBC news anchor, Tomasz Schafernaker, suffered backlash after stating on air that rain would fall “mainly in Nowheresville” and gesturing toward northwest Scotland. The Scots were offended although Schafernaker later apologized and said he was actually talking about the Highlands in an areas where only a few sheep reside.

What does “hold your horses” mean?
Stop complaining
Be patient
Be quiet
Keep your kids under control
Correct Answer
Wrong Answer

This phrased started as the Americanized, “hold your hosses.” Hoss is an old-fashioned American slang term for the word “horse.”


Which of the following means “a predicament or awkward situation”?
“A fine kettle of fish”
“Flutter bum”
“Negative perspiration”
“Smog in the noggin’”
Correct Answer
Wrong Answer

“Bless the seven little men who have been so kind to me, amen. Oh yes, and please make Grumpy like me.” “Hah! Women—a fine kettle of fish!” –Snow White and Grumpy from Snow White and the Seven Dwarfs

What does “paint the town red” mean?
Go steady
Get messy
Act wild
Correct Answer
Wrong Answer

There are several origin stories, including an event in England where Marquis Henry de la Poer Beresford is said to have painted the town (and some night watchmen) red in 1837. However, the earliest printed references seem to begin around 1883 in America and may be related to turning the entire town into a “red-light district.”

What does the phrase “can’t cut the mustard” mean?
Used when military personnel are subject to disciplinary measures
Having digestive problems
Not up to high standards
A butcher who makes sloppy cuts of meat
Correct Answer
Wrong Answer

“He tried to run the post office business under Cleveland’s administration but couldn’t ‘cut the mustard.’” –The Ottawa Herald, August 1889 (the earliest known instance of this appearing in print)


What does “the cat’s meow” mean?
It’s very good
Off-key music
An annoying person
A request that is difficult to fulfill or confusing
Correct Answer
Wrong Answer

The definitive (but disputed) cat dictionary was compiled by Mildred Moelk in 1944. She stated that there were three categories containing 16 different sound patterns cats make.

Which of the following means pursuing a wrong or misguided assumption?
“Being full as a tick”
“Barking up the wrong tree”
“Colder than a brass toilet seat in the Yukon”
“In the ketchup”
Correct Answer
Wrong Answer

“Everyone wants to understand art. Why not try to understand the song of a bird? …People who try to explain pictures are usually barking up the wrong tree.” –Pablo Picasso

A man saying “When the rubber hits the road” is referring to what?
When you get in trouble
When you get depressed
When a theoretical idea is tested in real life
When you leave home and finally get out on your own
Correct Answer
Wrong Answer

The idiom refers to where car tires touch the pavement. It seems to have originated in the 1950s.


What does “jump ship” mean?
Run your business aground
Abandon what you are doing
Travel around the world
Boisterous and loud
Correct Answer
Wrong Answer

“Investors repeatedly jump ship on a good strategy just because it hasn’t worked so well lately, and, almost invariably, abandon it at precisely the wrong time.” --David Dreman

What does “close but no cigar” mean?
You won, but you aren’t getting a prize
Just missed being successful
You are too tense
You had a supernatural experience
Correct Answer
Wrong Answer

At one time in the United States, games at the fair gave away cigars as prizes and this is thought to be the origin. The 1935 film version of Annie Oakley contained the line, “Close Colonel, but no cigar!”

What does the phrase “everything but the kitchen sink” mean?
Most of the ideas are useless
There are a couple of flaws in your plan
You forgot something you really need
Lots of things
Correct Answer
Wrong Answer

“Life will throw everything but the kitchen sink in your path, and then it will throw the kitchen sink. It's your job to avoid the obstacles. If you let them stop you or distract you, you're not doing your job, and failing to do your job will cause regrets that paralyze you more than a bad back.” –Andre Agassi from Open


What does “put a sock in it” mean?
Be quiet
Your hands are cold
Your head is empty
I’m going to give you a black eye
Correct Answer
Wrong Answer

This one originated in the United Kingdom in the early 1900s. The first place it appears in print was in a literary review titled The Athenaeum (1919).

What which of the following means ”stay calm?”
“Cry crocodile tears”
“Beat about the bush”
“Keep your shirt on”
“See a man about a dog”
Correct Answer
Wrong Answer

“Keep your shirt on. Let me read.” –The Grandfather in the Princess Bride

You Got: