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1.
One of the most amazing movies ever. My all-time favorite Johnny Depp/Tim Burton film.

In the early United States of America, young policeman oh-so-bangable Ichabod Crane (Johnny Depp) is sent to from New York to the fledgling settlement of Sleepy Hollow to investigate a series of ghoulish murders. On his arrival, the town council informs him that the three victims were killed in open ground, and the heads had disappeared - taken by a headless ghost that is supposedly responsible. Ichabod is unconvinced of this, but learns more about the ghostly horseman - it is the ghost of a Hessian sent by the British during the revolutionary war, and he was caught by redcoats and decapitated with his own sword. When Ichabod sees the ghost kill one of the town council members, his skepticism evaporates - and he soon discovers that the horseman's ghost has an unholy connection to Balthus Van Tassel, a wealthy farmer - and whose daughter, Katrina (Cristina Ricci) Ichabod is falling in love with...
1. Sleepy Hollow is amazing.
2. ICHABOD IS FUCKING HOT.
3. One of Tim Burton's greatest films.
by BabiesAreTheNewBlack April 28, 2007
 
2.
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
 
3.
Sleepy Hollow is a nice and very wealthy living area in Marin County, Ca. It is home to some of the richest middle class people you will find. It also has one of the most successful swim teams and is seeming to have many young studs coming up. Most of the kids in the area are nice and sports minded primarily. Most kids from this area address themselves as HollowFornians. These tend to be some of the most athletic kids in the area with reputations as the nice guys you don't want to get in a fight with. This clan of teens is not deemed as violent, but has had counts of beating up kids from other areas. I have been told that the new upbringing of HollowFornia kids can be identified by a shirt with The writing Hollow Fornia on it. Although i Have never seen this. And again only the younger ones ranging from ages 10-17 have been said to have these. There is no real identification for older HF's except for them always being in groups walking or driving down the streets. Sleepy Hollow's violence comes mostly from drunk teenagers in cars shooting and or throwing objects at people on the street. The shooting is with paintball guns or pellet guns.
Where are your from?
- Sleepy Hollow .
-O really?
-yeah hollowfornians for life
by freshkicks' April 20, 2010
 
4.
A Dried up old vagina, typically under used and over age.
Dorothy had to borrow blanches lube when Stanley couldn't get his dick into her sleepy hollow.
by Thegoldengirls October 21, 2013
 
5.
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
 
6.
The sleepy hollow is when you have a very drunk, passed out girl in your bed. Instead of being the nice guy you normally are, you proceed to insert your penis into each and every hole. While coming to realize she was a complete and utter slut (every hole felt like a hot dog down the hallway). At this point you come to understand she fell asleep in your bed for that reason.
Nathan Pridemore decided to take full advantage of a freshman girl only to realize she was a sleepy hollow.
by Ian Wilson September 18, 2007