Pleasantville is a small town in Westchester New York, which is anything but pleasant. There are a couple of bars, a grocery store, liquor stores and that’s basically it. There are a few schools in Pleasantville; Pleasantville High School where the students are put into a plastic bubbles by the administration there and are not allowed to do anything, Pace University where the students crowd the best bars in town (Paulies and Michaels) 5 out of the 7 days a week, and the best school of all: The Cottage School where the "students" are anything but good (look up a news report on this school). Weekend nights are kinda boring. If you don't have an ID or know someone, good luck getting into Paulies or Michaels. Occasionally the high school kids throw woods parties and very rarely house parties because everyone breaks each others stuff. If you want to have a good laugh or just be completely grossed out, just sit by the Pleasantville Pizzeria and you'll see the huge black transvestite, Shanaynay in fish net clothing and a feather scarf walking around. Also everyone knows everybody else, what you did, and who you did it with. You'll probably hear things about you that you didn’t even know yourself. Sounds like a great place to live, right?
Pleasantville Lady: “I’m sorry to hear your parents are getting a divorce."
Pleasantville kid: "They are?! They didn’t tell me yet"
by Anonly March 16, 2007
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Pleasantville is a small town in Northern Westchester, New York. It is less than 2 miles in diameter. The majority of the town is white, preppy, and moderately wealthy. Although it is a pretty town, the people are jerks. Everyone feels they have the need to know everyone elses business, and then feel the need to make sure everyone else knows as well. The town has 2 pizzarias, a coffee shop, and coldstone. woo-hoo.

and no, pleasantville is Not in black and white, so stop asking-its not funny anymore. or if its pleasant there.. thats annoying too.
jim: is it PLEASANT in pleasantville?
jim: is it black and white there? hahaha
by anonymus47283620432 August 28, 2006
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great 1998 movie about the loss of innocence and living life according to feeling and emotion, not how society tells us to live our lives. the film centers around 2 people who are transported into a 1958 TV show based in a town called Pleasantville where everything is perfect and pleasant. this film also teaches us why segregation is bad and why living life based on the same old routine just hides what we really feel inside. this film stars tobey maguire, reese witherspoon, and william H. macy.
quote from Pleasantville: "Honey! I'm home."
by mr. funnysunnyperson June 22, 2011
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A small town in westchester county ny. It is not rare to see groups of hoodlum 6 year olds flipping their shit all over town. For such a small town, there is an excess of donuts, frozen yogurt, pizza, and nail salons. But really, there are at least 8 nail salons within an area of less than two square miles. The schools are fine but are full of assholes who think they run the place. Hint: not the teachers. The train station is convenient because there aren't many interesting things to do here. The occasional party is quickly ended by the police or the parents, who are equally as frightening. So next time your driving south to the city, make sure you keep driving right past this "pleasant" town. PS- pleasantville is ravaged by wild westlakers who roam the town on Friday afternoons. Proceed with caution.
Foreigner- " what are they doing? "
Pleasanvillian- " who knows? this is pleasantville "
by GuessWho75 December 15, 2014
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Pleasantville, New Jersey:

Pleasantville is a city in Atlantic County, New Jersey, United States. As of the United States 2000 Census, the city population was 19,012.
Pleasantville was originally incorporated as a borough by an Act of the New Jersey Legislature on January 10, 1889, from portions of Egg Harbor Township, based on the results of a referendum held on December 15, 1888. Pleasantville was incorporated as a city on April 14, 1914, replacing Pleasantville borough, based on the results of a referendum held that same day.
Pleasantville Are you going to the rec in Pleasantville tomorrow?
by iMaj609 February 07, 2011
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Just like the movie it is pleasant and nice. In "Pville", everyone knows everyone in the village and the High School is a mere 500 students. A spec of catholisim in an area of jews (yeah u know it Briarcliff and Chappaqua). It is made up of almost all Irish-Italians. The kids in the village drink like it's their job. Alcohol is very prevelent in a small town with five bars and a very lenient police force. Pleasantville is the ideal place to raise a family. Its very white, very catholic, and everything about it is warm and high-class.
Q: Hey, what are those kids from Pleasantville, NY doing tonite?
A: Throwing it up, pong style!
by BiggieQ December 04, 2005
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A town that really isn't that pleasant. A small, ugly town in Westchester, nothing special about it except for the Jacob Burns Film Center, which no one in Pleasantville goes to anyway. Boring town with lots of girls with badly dyed blond hair.
Person: Oh, you live in Pleasantville? Is it pleasant there?(laughs)
Me: (fake laughs)Yeah...(plots to kill person)
by heather September 17, 2004
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