Someone who takes videos of himself squatting naked on a pie, preferably of the cream type variety, and masturbating much to the delight of his intended viewer.
He's in the other room making a video with a pie. He's a Hoboken Squat Cobbler.
by Yankwood February 25, 2016
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A fetish involving watching someone sitting their posterior into a pie (preferably apple or pumpkin, but this is up to the fetishist) and wiggling said buttocks around in the aforementioned dessert
Jimmy: Yo, did you catch that Hoboken Squat Cobbler video on the Tube?

Chuck: Yeah man, got me rock hard
by cellophanefriend February 23, 2016
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When a fully clothed person sits in a pie (or other cake like pastry) and commences to weep like a little girl. Squat Cobblering is usually engaged in by ugly, bald, middle aged men, who usually have some form of what appears to be mild autism. Said mild autism may manifest itself in an childlike, irrational and downright creepy obsession with baseball cards.
Did you see the back of his pants? He either crapped'em, or Hoboken Squat Cobbler'd a chocolate cake.
by Bob Barr 123 February 26, 2016
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Hoboken squat cobbler is a sexual fetish act where a man or woman, fully clothed, slowly sits into a pie while singing a seductive song. The singing is what differentiates this from other pie-sitting fetishes, it is named after the hometown of Frank Sinatra, who is rumoured to have fathered the act during one of his famous drinking binges at a friends' birthday party. Frank Sinatra allegedly said at the time "Let me show you what we call the hoboken squat pie."
The party was going fine until Jamie gave everyone the hoboken squat cobbler.
by SwampBeast February 23, 2016
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1. A redneck/hillbilly/very countryside person who lives along the Hoboken highway (goes from New Jersey to Penn)
2. A suburban/urban person living in the East Coast who either wants to be a hillbilly or is obssesed with very country things.
You like all of the redneck pages online? You are such a Hoboken hillbilly.

Jake is a Hoboken hillbilly
by yeetboi990 July 17, 2019
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