Playboy Jokes - 57 Hilarious Playboy Jokes

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A millionaire playboy dies, and meets St. Peter at the Pearly Gates

St. Peter looks at the list of everything he's done in his life, and sends him to Hell.

The playboy re-appears in Hell, but it looks like a huge, fancy cocktail party. All the men are in tuxedos, the women are all beautiful and in tight black dresses, and there are champagne bottles popping ...

Timbuktu

This one I got from Playboys joke page in the late 80s.

Two guys with identical education and experience were applying for the same marking position in a company. The hiring manager could not decide which one to give the job offer to, so he calls them both in for a final interview at the sam...

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After a night at a singles bar, a man in his late 60's chats up two girls in their 20's, and talks them into a three way at his place the following evening (NSFW)

The next day, the pressure of satisfying two, substantially younger women begins to weigh on him. He goes to local pharmacy, and after some discussion, the old playboy heads home with a box of viagra.

The next day, he returns.

"I think I need your help again" he says to the ph...

An old country preacher had a teenage son, and it was getting time the boy should give some thought to choosing a profession.

Like many young men his age, the boy didn't really know what he wanted to do, and he didn't seem too concerned about it.

One day, while the boy was away at school, his father decided to try an experiment. He went into the boy's room and placed on his study table four objects:

1. A Bi...

Read This One In Playboy Decades Ago

You older pervs will have heard this one.

So a young couple were out driving late, and got caught in a snowstorm. Wouldn't you know it? The car stalls while they're out in the middle of nowhere, and has to pull over to the side of the road.

The man pops the hood, exits the car & pr...

Read in "Playboy", told by CC, herself, on "the Tonight Show"

Cindy Crawford and a crewman survive her yacht sinking and make their way to a deserted island. There's fresh water and plenty of fruit to eat, so they settle in to wait for rescue. A few weeks go by and Cindy's feeling a "need". She asks the crewman for help and he's happy to oblige.

This...

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A man is on his way into the pub when a nun steps in front of him...

...and says, "Stop! For the sake of your soul, I implore you!"

The man takes a step back and says, "Can I help you with something, sister? I was just on my way in for a pint."

"A pint?" she asks, "Twenty pints is more like it! You were going in there to get drunk, and drunkenness is a ...

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A man with no arms and no legs is sat on a beach

A man with no arms and no legs is sat on a beach when he spots three playboy bunnies walking by him. They all spot him and feel bad for him so they try to cheer him up.
The first playboy bunny walks up to him and says; "Have you ever been hugged?" The man shakes his head so she gives him a hug.<...

Why do pirates love Playboy Magazine?

You'd think it's for the booty, but they really read it for the arrrticles.

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A guy dies and suddenly finds himself in Hell...

He trepidatiously follows the crowd towards the Gates of Hell. He finds a demon holding a piece of cardboard with his name on it.

"Craig?," asks the demon as the man approaches.

"Y... yes," answers Craig, unsure of how to handle the situation.

"Hi. I'm Ed. I know what you're thi...

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Little Johnny reads a Playboy

(Joke about Women, don't read if it will offend you) Little Johnny gets caught by his dad looking at a Playboy magazine under his covers.

 

- His dad says son, what are you looking at that for?
- Johnny replies, "well I'm trying to figure out what a pussy is."
- His dad...

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A bear and a rabbit stumbled upon a magical lamp in the forest...

They rubbed it and guess what, a genie appeared. He granted both of them 3 wishes each. The rabbit asked the bear to go first, becuase he knew the bear's playboy nature.

Bear: I wish to be the most handsome bear in the whole world.
Genie: Granted.
Rabbit: I want a motorbike.
Genie (a...

What do reddit and Playboy magazine have in common?

No one actually reads the articles.

What do you call a toilet at the Playboy Mansion?

A jackpot

A monk was selling flowers on the Playboy mansion grounds and no one but Hef could get him to leave...

Only Hugh can prevent florist friars.

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Donald Trump has a problem.

Donald Trump has a problem.

He's had a long life of being a rich playboy, womanizer, having lots of sex. Recently, however, no matter what he does, he can't have an orgasm. He's tried sexy outfits for Melania, Viagra, porn, porn *stars,* Japanese massage parlors, fleshlights, pills from the...

At one point, playboy tried to capitalize on the MILF craze but was wildly unsuccessful.

It turns out nobody wants to ask the person running the register if they got the *Mommy Issues.*

What's the difference between the Circus and the Playboy Mansion?

If I went to the mansion I would be the elephant in the room.

What's the difference between a gymnastic team and a playboy model?

The gymnasts do a bunch of cunning stunts.

Some monks were selling flowers outside the playboy mansion

Hugh Hefner realises this and puts a stop to it as they are on his property and welcoming tourists. The local news catches wind of this and goes to interview the monks.

The reporter asks "do you think you will set up shop somewhere else?"

And the monks reply "oh yes, only Hugh can pr...

Why was the playboy stressed?

He had a lot of thots in his mind.

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Damn girl are you playboy magazine?

Cause holy fuck you have a pile of issues

Our top story tonight: Famous playboy hugh hefner...

Famous playboy hugh hefner managed to stop an order of monks from operating their buisiness on his private property. The police forced the friars to close down their stall, located just outside the playboy mansion, where they had been selling flowers. When interviewed, one monk said: "Well, if it wa...

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The "penguin"

A guy who's strapped for cash asks a prostitute what he can get for $10. She replies, "Well, for 10 bucks I'll give you a 'penguin.'" "Okay... Sure, I'll take it."

So she gets down on her knees, lowers his pants, and begins giving him a blowjob. But right before he is about to cum, she gets ...

New playboy magazine

Q. Did you hear about the new magazine for married men published by Playboy?

A. It has the same pictures month after month after month after month after month....

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What’s more horrifying than finding a stack of dad’s playboys in the basement?

Realising one of them’s still breathing.

I have discovered there is something worse than finding your grandpa’s stash of playboy...

It’s figuring out the reason why some of the pages are stuck together!

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The Penis Study

In 1991, Duke University funded a study to see why the head of a man's penis was larger than the shaft. After one year and $180,000.00, they concluded that the reason the head was larger than the shaft was to give the Man more pleasure during sex. After Duke published the study, Stanford decided to ...

An 80 year old man married an 18 year old girl

He goes to see his doctor to ask advice on starting a family as he wants an heir, as he had been a playboy all his life and never settled down.

The doctor smiles at his request and says best thing is to get a young lodger. He thanks the doc saying yes she could do with some younger company a...

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A mother is concerned about her sons future

... so she goes to here priest and says "father, I'm concerned for my boy! He doesn't seem to have any ambitions and I'm concerned he won't amount to anything!"
So the father says to her "do not worry, take me to your home and I shall put your mind at ease."
So she takes him to her house and...

I accidentally subscribed to the "married man" edition of Playboy.

It's got the same centerfold every month.

Police responded to a call outside the Playboy mansion.

Mr. Hefner called the police to remove a group of monks selling daisies out of an illegal roadside stand in front of the Playboy mansion. A police spokesperson released a statement "we responded promptly to Mr. Hefner's call because as everybody knows, only Hugh can prevent florist friars."

What did the teenage boy do with his first issue of playboy?

Beats me.

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A man was reading a newspaper

when his son suddenly barged into the living room. He was all sweaty and out of breath, but had a big smile on his face. “Dad!” exclaimed his son, “I just lost my virginity!” The man put down his newspaper and looked at his son proudly. The young man standing before him reminded him of his youth, wh...

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A mother cleaning her adolescent sons room finds a stash of hardcore German S&M porno mags...

Mortified, she puts them back so he won't know, but hides one in her apron to show her husband. Later that night they're in bed and she shows him the magazine... The father chuckles at first, assuming it was a Playboy, or Penthouse, but quickly becomes horrified at the images of whippings, and ball ...

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A traveling salesman approaches a home...

He rings the doorbell, and a 10 year-old boy answers the door.

The boy has a scotch in one hand, a playboy tucked under his arm, and a lit cigar hanging from his mouth.

Salesman: "Uh, son, are your parents home?"

Boy: "The fuck do you think?"

I had a dream.

Last night I had a dream. I dreamed that Hugh Hefner, publisher of Playboy died and went to Hell. He was trapped in a small room with no doors or windows with an unattractive, hateful woman. A voice boomed out from nowhere and said: "Hugh Hefner, for your sins in life you shall spend eternity wit...

The owner of hostess just brought the playboy mansion

Guess he really liked ho-hos and ding dongs

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a man goes to confess after 25 years

So the man walks into the confession booth for the first time in his adult life, having nothing but bad memories about it from when he was a child.
So he opens the door, sits down and notices a couple of playboy nude calenders on the wall, a bottle of whiskey in the corner and a nice box of cigar...

Subscriptions

Steve and Cliff are having this talk. Steve says, "My wife lets me subscribe to National Geographic and Playboy for the same reason." Cliff says, "Why?"

Steve says, "Because with both magazines, I get to see places I'll never get to visit."

Hugh Hefner was sitting in the Playboy mansion, admiring 'the view'

He then heard there were a group of people at the door, trying to sell him flowers.

He went out and said, "Can I help you?"
"HI sir! We are from Rainbow Florists and would like to know if you want to buy some beautiful flowers for your beautiful ladies?"

"Get the hell off my propert...

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Couples coffee (OC WIP)

A priest, a marriage counselor, and a notorious playboy are all at of a romantic breakfast for couples event when the announcer gets on stage and pulls back a curtain to reveal a coffee-making robot with hundreds of robotic arms. He announces that this robot automatically makes coffee for both the p...

Going To The Movies

I told my wife I wanted to watch a movie about a billionaire playboy with a penchant for darkness, inflicting violence and dressing up in masks.

She got excited and asked, "Are we really go to see *50 Shades*?"

I laughed and told her I was talking about *The Lego Batman Movie*.

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The toughest cowboy

Three cowboys were sitting around the fire telling ole cowboy stories to prove how tough they were. The first cowboy said " One time there was a ragin' bull, runnin' wild in the town, destroyin' everything! So I ran em' down, grabbed em' by the horns and resettled him to the ground ". The second cow...

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Story of the joke funnier than the joke.

I used to work with this crazy Vietnamese jeweler who was always asking to tell him jokes. One day I remembered one I saw in Playboy many years ago...

A guy is driving home from work and realizes that when fooling around with his secretary, she had given him a hickey on his neck. His mind sta...

A group of Franciscan Monks arrived at the front of the Playboy Mansion

They all started setting up shops. One by one, they would close down, and the only carts that remained sold flowers.

The police and the media started to show up, amazed that the monks were able to sell flowers on the Playboy Mansion front steps. Passers by would buy a rose, and pass the house...

Playboy returns to cover completely naked pictures of girls.

Trump is in office less than a month, and already makes America great again.

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The Fortune Teller

Guy walks into a bar and sees a machine in the corner labeled "The Fortune Teller". He asks the bartender what it does. The bartender says, "You put in a dollar and get a cup. Go piss in the cup, put it back in the machine and it'll tell you your fortune ...and it's never wrong." The guy replies "Bu...

Three guys are stranded on a deserted island

One of the guys finds a lamp with a genie inside.

The genie says: Thank you for freeing me. In return, I will grant you a wish each.

The first guy says: I wish I was at home with my wife and kids!

"As you wish" the genie says. Poof and the guy is at home with his wife and kids.<...

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Old man at work told me this one!

What's the difference between a vagina and a cunt?

"You know when you open that playboy centerfold and you see that little triangle shape between her legs?" "That's the vagina....everything else around it is a cunt."

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What's the difference between a naked white woman and a naked black woman

One is on the cover of playboy while the other is on the cover of national geographic

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Mommy frog went out to get some groceries

so she tells her two little boys, Steven and James, to be good little frogs while she was gone. Seconds after she went out, Steven excitedly tells James he knew where daddy frog hid his long-kept porn stash. James thought that the idea of "borrowing" their dad's vintage Playboys and 80's VHS is bad ...

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Three friends catch the same goldfish

The goldfish says:
-“You know the rules, whoever catches me gets three wishes. Since you three caught me together you get one wish each. Each of you take an egg, go home break it and say your wish, it’ll come true.”

The first friend breaks the egg and wishes for money. The room fills wit...

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[NSFW] There's two fellas way out in the woods in Virginia...

The name of one is Cecil. It's not important what the other one's name is.

They're bored, just trying to kill time while they whittle.

The more talkative fella, he says to Cecil, "Have you ever heard of the game 20 questions?" And Cecil says, "Nope."

"Well, the way you play i...

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Little Johnny is hanging out with the older kids at school

When one of them starts talking about his ex girlfriend and calls her a cunt.

Little Johnny has never heard that word before.

Later at home, he tells his mother about the older kid calling his ex girlfriend a cunt. Johnny asks his mom, what is a cunt?

Little Johnny's mother does...

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An ex-businessman, now bankrupt, is preparing to jump off a bridge...

As he's about to step into the void, a hand grabs him from behind.

He turns back annoyed and sees that the hand belongs to an old bearded overweight guy.

"Why did you stop me you old fool?"

"Have you gone mad my son? You were about to kill yourself!" The old ma...

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Pussy and Bitch

A kid comes home from school and says to his mom, "Mom I've got a problem."

She says, "Tell me."

He tells her that the boys at school are using two words he doesn't understand.

She asks him what they are?

He says, "Well, pussy and bitch."

She says, "Oh that's no bi...

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