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Sleepy Hollowed

To be decapitated by an axe or sword by someone preferably riding a horse or motor cycle. Basically, it's a drive by beheading.
Did you see that movie "300" when that dude's son gets sleepy hollowed right in front of his dad?

Yeah that shit was epic!!
by Taborific March 30, 2009
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Sleepy Hollow Country club

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".
Mommy, Im going to play golf at the SLEEPY HOLLOW COUNTRY club today.

Dad, why is my boyfriend a better golfer than you?
by Mike HOCKEY11287 December 15, 2006
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Sleepy Hollow

A: Noun: An act of sexual intercourse wherein the couple is engaged in "doggy style" and the receiving partner is unaware that the active partner has placed a pumpkin, or Jack O Lantern upon his head. When the receiving partner turns to look, she is greatly startled and oftentimes thoroughly scared by the sight.

B: Verb: The act of placing a Pumpkin or Jack O Lantern upon ones head during sex with the intention of "Fucking With" one's partner.

Note: First Invented at Drew University. Most Appropriate around or on the time of Halloween.
"Dude! Last night i was banging this chick, and i Sleepy Hollowed Her! It totally freaked her out, though. She hasn't answered any of my calls."

"Hey Bro! We should totally grab some of those Jack O Lanterns in front of Hoyt and Sleepy Hollow some chicks tonight!"
by JFins October 18, 2009
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Sleepy Hollowed

When you fuck a bitch until you cum and then you chop her head off with an ax
Yo i Sleepy Hollowed that bitch last night, she's dead.
by z69Malcolm69z February 24, 2009
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Sleepy Hollow

The act of falling asleep with an erection.
"Bro I went to sleep full sleepy hollow and woke up with morning wood"
by 69WeenieBoy69 January 25, 2017
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sleepy hollow

a bunch of losers who suck at sports and only in their DREAMS can they be as cool as the kids from Ossining
by posess February 7, 2019
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Sleepy Hollow

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.
by I Am Sasquatch September 29, 2011
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