Mr. Montgomery is the owner of Montgomery farm, a plantation that uses telemarketers kidnapped by the Montgomery family to work the fields. When Montgomery was a child, his father was repeatedly hounded by a telemarketer that led to the death of him and his workers. His father's last words "Telemarketers are the Devil!"' inspired his son to seek revenge on all telemarketers by enslaving them.

Mr. Montgomery kidnapped Stanley Goodman along with his coworkers and boss, causing the Goodman family to start looking for him. When he was visited by Livingston Bumblesworth, Mr. Montgomery has his telemarketers act out a play to make him look good. When Stanley started to mock Mr. Montgomery in his imitation of him, Mr. Montgomery agreed to act out a scene where he pretends to be a telemarketer and tries to sell Stanley something to see how hard it is. When Stanley does show him how difficult it is, he convinces Mr. Montgomery to buy a guitar weedwacker and end the feud between farmers and telemarketers. However, Stanley's wife enters the room holding guns to Mr. Montgomery's sons and demands he give back those telemarketers. The Montgomerys respond by getting out their guns with the intent to kill them. Mr. Pickles then arrives with a horde of snakes and uses them to kill Montgomery's associates, before killing Montgomery himself by striking his face with a guitar weedwhacker so hard he falls into the fireplace which burns down the entire building.