Sam & Max: The Devil's Playhouse - Episode 3: They Stole Max's Brain!

Note if at any point you fail to interrupt the person keep choosing until you get the 'Again!' option to restart the conversation

When you start Act 1 at the beginning of the game you will be thrown into a conversation with molemen after the initial cutscene, say the following:
Mole Men Dialog - Hurry up!
Mole Men Dialog - You're Lying!

You will then move to a new location and talk to one of Skun-ka'pe's Space Ape's, say the following:
Space Ape Dialog - Noir [1/6]
Space Ape Dialog - Threaten [2/6]
Space Ape Dialog - What Rat?!

You will then move to a new location and talk to Frankie, say the following:
Frankie Dialog - Noir [3/6]
Frankie Dialog - Threaten [4/6]
Frankie Dialog - Tell Me More!
Frankie Dialog - Again!
Frankie Dialog - Directions Where!?

You will then move to a new location again and talk to the Tourist, say the following:
Tourist Dialog - Noir [5/6]
Tourist Dialog - Threaten [6/6 Bad Cop/Sad Cop in Sam & Max: The Devil's Playhouse - Episode 3: They Stole Max's Brain! unlocked]
Tourist Dialog – Leave
Travel to Sign Spinner

Back to the Space Ape, say the following:
Space Ape Dialog - You're Lying!
Space Ape Dialog - Tell Me More!
Space Ape Dialog - Tell Me More!
Space Ape Dialog – Noir
Travel to Frankie the Rat

Back with Frankie, say the following:
Frankie Dialog - You're Lying!
Frankie Dialog – Threaten
Frankie Dialog - Hurry up!
Frankie Dialog - Hurry up!
Frankie Dialog - Tell Me More!
Frankie Dialog – Leave
Travel to Dark Alley

Back with the Tourist, say the following:
Tourist Dialog - Hurry Up!
Tourist Dialog - Hurry Up!
Tourist Dialog - You're Lying!

Trophy unlocked.