The following dialogs all contribute towards the trophy:
- Act 1 - Enter teleportation mode for the first time. - "Now select a phone number that Max has memorized, to teleport himself and his furry longtime companion to that location. And also Sam."
- Act 1 - Put homing beacon on Skun-ka'pe. - "Now we just use the remote control Momma Bosco gave us, and Skunkape gets sucked right in the Penal Zone! So to speak."
- Act 2 - Speak to Max about "Other planets", you'll need to first ask about the Presidency, and Sybil before the option appears. - "I don't need to go to another planet for a methane-rich environment, as long as I've got you, pal."
- Act 2 - Pick up the Jumper Cables from the DeSoto. - "It's simple, Sam: the RED cable goes on the RIGHT nipple, the BLACK cable clamps to the..."
- Act 3 - Exit conversation with Superball at the start of the act. - "We'll hit that gorilla where it hurts the most!" "Right in the Penal Zone!"
- Act 3 - Phone in pizza boxes - "Swallowed whole! I've never seen anything like that before!" - "Not since we accidentally wandered into that theater on Times Square."
- Act 4 - At the end of the opening cutscene of Act 4. - "Only YOU can return General Skun-ka'pe to... The Penal Zone!" "Tee hee."
- Act 4 - After being trapped in the Penal Zone. - "He just wanted to rub our noses in the Penal Zone! So to speak."
- Act 4 - Teleport back to Skunkape's ship after escaping from the Penal Zone. - "not only did I defeat Sam & Max, but I took care of the Penal Zone in one stroke!" "Unfortunate word choice."
- Act 4 - Talk to cultists about Rift Generator - "I gotta turn on this machine to stop a gorilla." "Down the tunnel, first door to your right."
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