Go outside and talk to the Maimtron. Tell it you have a question, and then ask "Why do fools fall in love?". It will turn its back to the open window while it thinks. Go back inside the building, then go to the window and take the turn key from the Maimtron's back.

In order to begin collecting the Horsemen, you must first get into Santa's Room at the North Pole. To do that, go into Santa's Workshop and talk to the green elf. Ask him what he's doing, tell him you can make him cry, and then choose Sam's "Santa isn't real." option. Grab the watering can and take it outside. To the left of the workshop is a tiny star-shaped bush. Use the watering can on it to make it grow, and then use it to go through the chimney and into Santa's Room. Once inside, take the parchment to learn about how to remove demons. Grab the Christmas record sticking out of the record shelf as well.

The trivia contest is in Stinky's Diner. Stinky cheats by saying every answer is wrong so that no one wins. There are three other people in the diner playing: Sybil, Lincoln, and the Bug. Sybil will always pick the correct answer, the Bug will always pick D which will always be a wrong answer, and Lincoln will pick whatever answer you tell him to. Work out what the correct answer is so you know what Sybil will pick, and then tell Lincoln to pick one of the wrong answers that isn't D. Finally, use the trivia pad in the empty booth and take the last remaining wrong answer for yourself. You answer last, so Stinky has no choice but to say your answer is correct after declaring the other three answers wrong and give you the Horseman.

See Trivia Manipulator for details on how to start the Horseman gathering quest.

Pimp Le Car is located in the garage down the street from Stinky's Diner. Open the garage and talk to the COPS. Ask them if they can pimp your car and tell them you want the Horseman. You will now have to play a mini-game where you drive the DeSoto and run over blue "Torture Me Elmer" dolls lying in the road. The controls are as follows:

Steer
Decrease speed
Increase speed
Honk horn (does nothing in this episode)
Use big gun; When using the gun, aims, shoots, and or puts the gun away
Remove VR goggles
Return to Straight Street

For this challenge, you shouldn't need to do more than just steer. Run over 30 Elmer dolls in 60 seconds and you will win the Horseman of Death. The COPS will attach it to the hood of the DeSoto, so go back to where it's parked and remove the Horseman.

See Trivia Manipulator for details on how to start the Horseman gathering quest.

Go into Bosco's Inconvenience and ask Bosco about his package. He'll reveal that his mom sends him a bomb every year and he's not sure if he can hear the bomb ticking or not. Head back to the North Pole and go into Santa's Workshop. Head to the green computer and use it to dispense a "Obsess-o-matic stopwatch". Pick up the gift tags on the counter next to the present, and then use the gift tags on the present. Send the present to Bosco. Then head back to Straight Street and go back into Bosco's Inconvenience, where Max will automatically open Bosco's original package and take the Horseman that's inside.

See Trivia Manipulator for details on how to start the Horseman gathering quest.

First, you'll need to pick up the Boxing Betty toy from under the Christmas tree at Santa's Workshop. Then head back to Straight Street and go back to where the broken Maimtron is. Talk to Jimmy and you'll learn that the Horseman of War is his trophy for being the boxing champion. Use Boxing Betty with the robot innards to begin a boxing mini-game. Use to dodge, and or to attack. The strategy for all three rounds is the same. Each opponent will raise up one of their fists to signal that they're about to attack. Move to the same side of the screen that the raised fist is on to dodge, and after the opponent has missed, use either or to attack them. If you attack them at any other time, they will always block. Once you defeat all three opponents in a row, you will be the new boxing champion and be awarded the Horseman.

After obtaining the four Horsemen, head into Santa's Workshop and go to the North pole. Use all four horsemen with the North pole to place them around it. Now examine the red computer at the gift dispenser and the slimy crate near the exit of the workshop to learn about the demon. Then use the Christmas record (found in Santa's Room if you didn't take it when you started the Horsemen quest) with the record player next to the North pole. You must now sing the Happy Demon song to complete the exorcism. Choose the "Like gelatinous goo!", "In Lower Manitoba!", "Like Mimesweeper!", and "Hey, Shambling Corporate Presence!" options. If done correctly, the demon will be removed and the trophy will unlock.

To begin, you will need to enter Santa's Room after the exorcism and open his safe. You will find a bottle with the spirits of Christmas inside. They will come out and ask you to fix three Christmases you ruined. There will now be three portals outside of Santa's Workshop.

The first thing you need to do is take the World's Simplest Maze from under the Christmas tree in Santa's Workshop. Then go outside and enter the portal to the past. Place the World's Simplest Maze in front of the rat hole, and then turn on the TV. Jimmy's wife will come out of the rat hole and get stuck in the maze, and Sam will place her in his inventory. Now head back to the present and return to Straight Street. Go back to Sam & Max's building where Jimmy has been threatening to jump after you beat him at boxing and use his wife with him to get the boxing glove. Head back to the North Pole once again and to back through the portal to the past. Give past Jimmy the boxing glove, which will satisfy the Spirit of Christmas Past.

See The Spirit of Christmas Past for details on how to start the Christmas spirit quest.

Go through the portal to the present outside of Santa's Workshop to witness the Bug's family coming to visit him at Stinky's Diner. Leave Stinky's Diner through the portal, and grab a snowball from the yellow snow reclamation area outside of Santa's Workshop. Now head back through the portal to the present once more and use the reclaimed snowball on the Bug family. The other bugs will leave and the Spirit of Christmas Present will be satisfied.

See The Spirit of Christmas Past for details on how to start the Christmas spirit quest.

Go through the portal to the future outside of Santa's Workshop to witness future Sam & Max trapped on a small island surrounded by lava. There's nothing you can do right now, so return to the present and head back to Straight Street. Go into Stinky's Diner and ask Stinky how business is. She will complain that her feet hurt. Head back to the North Pole and enter Santa's Workshop. Use the green computer to dispense a "foot bath and piranha aquarium", and then use a gift tag to send the present to Stinky. Head back to Stinky's Diner and pick up her sock from the counter. Return to the North Pole with the sock and enter Santa's Room. Put Stinky's sock into the stocking stuffer, which will fill the sock with coal. Take the coal back outside and put it in the boiler at the back of the sleigh right next to the portal to the future. The sleigh will be used to save future Sam & Max and the Spirit of Christmas Future will be satisfied.

After satisfying all three Christmas spirits, go to the demon that's next to the DeSoto outside of Santa's Workshop and use spirit bottle on it. The spirits will take care of the demon and the trophy will unlock.

After the spirits get rid of the demon, you'll find yourself stuck in a shootout with Santa inside of his workshop. First, use the green computer to dispense a gift. Use your big gun to shoot the switch on the wall next to the exit of the workshop. The switch controls the toy airplane that's flying in circles overhead. Try to stop it above the trampoline, and then shoot the cannon. The cannon will fire, the ball will hit the present you dispensed and bounce off onto the trampoline. If the plane is in the right spot, the cannon ball will bounce off the trampoline and into the toy plane. Once the ball is inside the plane, shoot the switch again to get the plane moving again, and then shoot the switch once more once the plane is above Santa and the giant fish toy that's behind him. If done correctly, the plane will drop the cannon ball into the fish, which will then launch the ball at Santa, and then the trophy will unlock. If you miss, repeat the above steps to reload the plane with a new cannon ball and try again.

NOTE: The gun shooting tends to be a bit picky. Often times, Sam will put the gun away and try to walk out to whatever object you wanted to shoot instead. When this happens, just pull out the gun again and try shooting again.

MISSABLE! See Pimp Le Car Driving Challenge for instructions on how to control the DeSoto. After you have obtained the Horseman of Death by completing the first Pimp Le Car challenge, there are 7 decals you must collect in order to unlock this trophy. Note that for the first four decals, you can press while driving to remove the VR goggles and drive around trying to get them without the COPS interrupting you every minute to inform you that you failed the challenge, but the last three require that you put the goggles back on.

• Bowling Pin: A set of bowling pins will randomly spawn in the middle of the road. You must knock all of them down to get the decal. Try to line up the DeSoto so that the white road lines are running directly underneath the "822" portion of the license plate and then leave it there while you pull out your gun to go for the following three decals. When the pins come up, your car should already be in the right spot to knock them all down. Pay attention when you see the pins coming though, so that if you miss any, you can see how far off you were and adjust your position accordingly.
• Piano: A piano will randomly spawn on the right side screen, hanging in front of the windows on the buildings you're driving past. Aim your gun at those windows and keep firing until the piano spawns to ensure you hit it. This tends to spawn when there are train tracks overhead blocking your view of where it's actually hanging, so aiming at where it will be and shooting is the best way to make sure you get it even if it's not visible.
• Blimp: A giant blue "Good Tire" blimp will randomly spawn in the top left section of the sky and move a bit towards the center before quickly disappearing. Keeping aiming your gun at the top left section of the sky and fire until it spawns to ensure you hit it easily.
• Cheese Wheel: A red cheese wheel will randomly roll across the road, going from left to right. You can either run over it with the DeSoto or shoot it with the gun. There's no solid place to leave your gun cursor to keep firing for this one as it's always moving. You can either try shooting it if you're still also waiting for the bowling pins to show up, or work on the last three decals and try to drive into the cheese wheel. I found that the latter worked best for me.
• Bronze Elmer: Another Elmer challenge like the one you had to do to win the Horseman of Death. This time you must get 40 Elmers in 60 seconds. You need to have won the Horseman of Death to attempt this.
• Silver Elmer: Yet another Elmer challenge, this time you must run over 50 Elmers in 60 seconds. You need to have won the Bronze Elmer decal to attempt this. This decal will replace the Bronze Elmer decal.
• Gold Elmer: The final Elmer challenge, this time you must run over 60 Elmers in 60 seconds. Pressing to increase your speed may prove useful, as will staying near the left sidewalk as many Elmers seem to spawn there. You need to have won the Silver Elmer decal to attempt this. This decal will replace the Silver Elmer decal.

Note that the four random objects you need to find for the first four decals can take quite a long time to appear. Be prepared to do a lot of driving with absolutely nothing happening while you try to get these decals. You must obtain all seven before using the Spirits of Christmas to get rid of the demon, as after you do that, you will be trapped in Santa's Workshop for the rest of the game.

MISSABLE! You'll find the Bug in Stinky's Diner while looking for the four Horsemen required to perform the exorcism. Simply start two conversations with him. When you talk to him the second time, he'll mention that it's his birthday and the trophy will unlock. You must do this before entering the Portal to Christmas Present, as when you do his family will arrive and you can no longer get the trophy.