a bunch of losers who suck at sports and only in their DREAMS can they be as cool as the kids from Ossining
Ossining is way better than sleepy hollow
by posess February 8, 2019
A competition held against oneself in which one ingests an entire bottle of Benadryl and furthermore attempting to ejaculate before losing consciousness.
Tyler: Hey dude, why do you keep a bottle of Benadryl and lotion by your bed.
Jacob: Oh, I got lonely, so I played a little Sleepy Hollow.
Jacob: Oh, I got lonely, so I played a little Sleepy Hollow.
by I Am Sasquatch September 30, 2011
The only school in the world where the minorities out-number the whites. Everyone wears a fitted hat, with colors that match their shirt, and shoes, the colors on the hat are never actually the team colors. If you wanna know where the party is at, you call John or DaVonn, because they have party-radar. Honors classes only means that everyone in the class can speak English. A majority of the white people dress like Abercrombie models, but they're not.
A normal Sleepy Hollow High School lunch:
Greg: YOU ARE NOT A RUFF RYDER
Andrew: What exactly does it take to become a ruff ryder?
Greg: Shut up Andrew you're drunk.
Andrew: Brian, what class are you skipping now?
Brian: Physics, bitch.
Greg: YOU ARE NOT A RUFF RYDER
Greg: YOU ARE NOT A RUFF RYDER
Andrew: What exactly does it take to become a ruff ryder?
Greg: Shut up Andrew you're drunk.
Andrew: Brian, what class are you skipping now?
Brian: Physics, bitch.
Greg: YOU ARE NOT A RUFF RYDER
by Whitesare Theminority January 14, 2006
The school located on North Broadway right off Beekman Avenue, that is made out of glass. Many yanyos, and dominicans, are waiting outside
You know your in sleepy Hollow High School when Spanish people are playing there regaton ringtones alllllll around you
by joey blank January 25, 2006
A mysterious place where the whites are constantly at war with the Hispanics, the drugs are used less than 30ft from the school itself, and nobody is quite sure who is running the show. Don't be fooled, it may have graduates who go on to well known universities such as Cornell and Penn, but this entire school is a madhouse. In order to survive one MUST follow the rules:
1. NEVER expect to be entertained at a football game.
2. NEVER expect to dance at a school dance.
3. NEVER remind a white kid acting black that he isn't black.
4. NEVER cross the crazy sub. She'll get crazy on you.
5. You have to be high in order to get what the fuck is going on around here, otherwise it isn't even worth a try.
1. NEVER expect to be entertained at a football game.
2. NEVER expect to dance at a school dance.
3. NEVER remind a white kid acting black that he isn't black.
4. NEVER cross the crazy sub. She'll get crazy on you.
5. You have to be high in order to get what the fuck is going on around here, otherwise it isn't even worth a try.
Student 1: "Hey wanna go to the church to do non-illegal activities?"
Student 2: "DIQQQQQQQQQQQQQQQQQQUE"
Tired of doing actual schoolwork and/or giving a shit? Go to Sleepy Hollow High School!
Student 2: "DIQQQQQQQQQQQQQQQQQQUE"
Tired of doing actual schoolwork and/or giving a shit? Go to Sleepy Hollow High School!
by xxxxxxxxxswaggiestxxxxxxxxxxxx November 30, 2011
A country club in Scarborough New York where everyone is worth over a million. Everyone has at least two houses other than the one they live in. If youre "Cool" from the club you grew up there and cant remember anything from your childhood without someone or something from Sleepy Hollow in it. Everyone owns a horse and rides it either there or at another barn. The idea of vacationing is never anything short of a private yaht or a private plane. Skiing locally means out west and skiing far away is in Europe. If you don't play all of the sports offered there you are not considered an athlete. 90% of the moms there run in the new york marathon and the general rule is once you turn 50 you need to loose 50 lbs. It has the most milfs out of any club, most of which are trophy wives. The men golf on the nicest course in westchester, daily, then come in to the clubhouse have a bottle of scotch and a cigar and meet the family for dinner. An idea of a "bad day" on the golf course is 2 over par. Most sons can beat their fathers and like their fathers are playing college lacrosse or hockey. Anything short of a top 20 school is considered "a good, unrecognized school", most kids go to rehab before this.
Bill Murray can be sighted on the golf course on a regular basis, knowing that some members have more money than even he does.
Every kid wants to marry someone from Sleepy Hollow at Sleepy Hollow and its planned since theyre like 3.
The kids from sleepy hollow are brats, theres no way to deny it. When theyre told a rule they consistently break it and no one there likes the new management because they put rules in, which the kids dont listen to. The response to most things is "do you know who my father is" then the subject is dropped. The response to work is, hire someone. The kids here dont have to do anything for themselves because they know that they can always live off daddys money. A relaxing day is taking your boat out on the hudson with a drink and your mom while dads golfing.
People want to be them but once your on the inside you claim you hate it when you know that the country club will get you more places than college will. Everyone from there knows that people want to be them simply because they are that privledged, they are "the shit".
Bill Murray can be sighted on the golf course on a regular basis, knowing that some members have more money than even he does.
Every kid wants to marry someone from Sleepy Hollow at Sleepy Hollow and its planned since theyre like 3.
The kids from sleepy hollow are brats, theres no way to deny it. When theyre told a rule they consistently break it and no one there likes the new management because they put rules in, which the kids dont listen to. The response to most things is "do you know who my father is" then the subject is dropped. The response to work is, hire someone. The kids here dont have to do anything for themselves because they know that they can always live off daddys money. A relaxing day is taking your boat out on the hudson with a drink and your mom while dads golfing.
People want to be them but once your on the inside you claim you hate it when you know that the country club will get you more places than college will. Everyone from there knows that people want to be them simply because they are that privledged, they are "the shit".
Mommy, Im going to play golf at the SLEEPY HOLLOW COUNTRY club today.
Dad, why is my boyfriend a better golfer than you?
Dad, why is my boyfriend a better golfer than you?
by Mike HOCKEY11287 December 12, 2006
by Bizserk July 22, 2018