Woolie Hole is a term coined by Matt and Pat used to describe a mysterious, darkened and typically dirty hole. It is heavily implied that the Woolie hole itself is a reference to fellow Best Friend Woolie's asshole. It is unknown as to why his asshole in particular is being singled out for such ridicule but it's likely just because Woolie is a favorite target of Matt and Pat's in general. Pat frequently mentions a possible operation Woolie had on his Woolie hole but it is unknown if this is for comedic effect alone or Woolie had an actual procedure to fix his Woolie hole.
Credit to YouTube user hugeackman for the picture, his fan video can be seen here.
- This running gag was first mentioned in episode one of the Silent Hill Homecoming series.
- It is speculated that "Woolie Hole" could also be referring to Woolie's apartment.
- In the Curse The Eye of Isis episode, it is stated that Woolie is upset at the repeated usage of the term.
- In Woolie's Reddit AMA, when asked what the Woolie Hole was, he stated that "Your guess is as good as mine".