Trick 'r Treat (2007)

Slated for release in 2007, then inexplicably pulled before it hit theaters, Michael Dougherty’s horror anthology Trick 'r Treat (2008) has gone on to become a beloved Halloween classic featuring one of the most iconic horror villains in recent memory. The film features three sometimes intersecting stories of different groups of people celebrating Halloween in Ohio. The first story follows Steven Wilkins (Dylan Baker), a murderous principal who gives bad kids poisoned candy, alongside his apprentice son Billy (Connor Levins). Then, there's Ronda (Samm Todd) a bullied young girl who ends up the victim of a cruel prank where a bunch of bullies pretend to be her friend, only to tell her about a class of children who were murdered by an evil school bus driver. The kids dress up as ghosts to try and scare her, only for the real dead kids to show up and show their lack of appreciation for those kids' impression of them. One of those dead kids is Sam (Quinn Lord), the burlap sack pumpkin mask wearing psycho who would become the standout character of the movie, in large part because of the segment where he attacks Mr. Kreeg (Brian Cox) the curmudgeon who hates Halloween because it reminds him of the day he killed all those kids on the school bus. But by far the best portion of the movie follows Anna Paquin as Laurie, the little red riding hood dressed babe who runs with a wild crowd but hasn't done the deed with anyone just yet. Nope, it's not the deed you're thinking of, since instead of sex a bunch of horndogs who follow these ladies into the woods come to realize these bad bitches are actually werewolves looking to pop Laurie's human chomping cherry. With all due respect to Sam, the scenes Mr. Skin best remembers all involve mams. Whether it's Monica Delain attempting to squeeze her humongous hooters into a pink bra as she tries on different costumes, or Amy Esterle's booby double dumping em out during her wolf transformation, Trick 'r Treat treated us to great teet!