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glengarry 

Traditional Scottish cap, made of wool, with two tails coming off the back. In the States, most often seen worn by bagpipers. Sometimes incorrectly spelled as "glangarry". Also called simply a "glen".
Piper 1: "Hey, have you seen my glengarry?"
Piper 2: "No...did you lose your hat again?"
glengarry by ThePiper June 13, 2004

Straight up the glengarry 

To penetrate the anus.

To go up the Garry Glitter (shitter)
things went well last night I went straight up the glengarry

glengarrulous 

(1) Excessively prone to quote from the David Mamet play (and film) Glengarry Glen Ross.

(2) In the habit of creating neologisms, usually for online dictionaries, that make reference, at some point, to Glengarry Glen Ross. (cf. mocquiesce, poortray, etc.)
I like Laura, but her conversation tends to be a bit glengarrulous.
glengarrulous by Worgus June 25, 2008