I just finished playing Grim Fandango Remastered, and got all the trophies in a single playthrough. With my extreme love of the game and many full runs through the game let me tell you how to get them all! Beware, because this list contains spoilers! You probably already knew that though, because you're looking at a trophy guide.
Note: Some of the trophy names have typos in them on PSN, which is insane. I typed everything as it should have been here,
Number Nine Ticket (Platinum)
Get all other trophies in the game.
The Right Way (Gold)
In order to get this you need to play with the tank controls for the entire game. It defaults to the new movement options, so go into options and switch to tank controls. Then start a new game, and play through the entirety of this remastered classic. It will be awarded to you during the final scene.
"What I did back in the fat days is none of your business. You know the rules." (Bronze)
When talking with Eva ask her what she did to get stuck in the Land of the Dead.
"Gets the aggression out, doesn't it?" (Bronze)
Eva has a hole punch on her desk. Use it while Manny isn't holding anything.
"Scaring the living is technically against the rules, but we all do it." (Bronze)
During the poisoning Manny travels back to the Land of the Living. Before you slice open the object in the middle of the room, talk to all of the living people.
It's like I'm not happy unless I'm breathing in the thick, black, nauseating fumes..." (Bronze)
When talking to Glottis for the first time ask him why he doesn't quit his job.
"Lousy bony fingers!" (Bronze)
When talking to the balloon twisting clown have Manny yell bang. This causes the clown to pop a balloon.
"I squeezed down one of these tubes, like a pixie!" (Bronze)
Talk to Brennis the purple demon who fixes the tube machine. Ask him how he got in there.
"Well I could do something bad right now if that would help." (Bronze)
After bringing Meche back to his office Manny starts to question her. Have Manny ask every possible question before leaving to tell Don what you've done.
"Precisamente, amigo." (Bronze)
Once you're in the Lost Souls Alliance base have Salvador explain why the D.O.D. is corrupt.
"Join or Die! Again!" (Bronze)
In the Lost Souls Alliance base ask Eva if she has any messages.
"'ARROGANT FRAUD' doesn't work." (Silver)
When Manny sneaks into Domino's office have him interact with the computer. Each time you do he will guess a different password. Keep going until he guesses Arrogant Fraud.
"Run you pigeons! It's Robert Frost!" (Bronze)
Ask the balloon clown to make you Robert Frost. Before you scare away the pigeons on the roof of the D.O.D. run at them with the balloon out.
"The marrow of these trees, Manny, they suck it out, it's like cement!" (Bronze)
During the puzzle in the forest with the wheelbarrow talk to Glottis.
"We only have one mop." (Bronze)
When you run into Celso in Rubacava ask him if he knows where to get a job.
"...Used to scream like a banshee when the trade winds blew..." (Bronze)
During the initial interaction with Velasco ask him what's under his eye patch.
Year 1 (Silver)
This is automatically awarded during the cutscene following year 1.
"Great news -- we've discovered a new, secret talent of our tiny messengers!" (Bronze)
When year 2 starts go inside. On the desk near the door you can pick up a letter from Salvador. If you continue to interact with it Salvador will say many things. Eventually he will talk about a new talent the pigeons have.
"Plus, we look good in these clothes!" (Bronze)
While Glottis is still at the piano in the casino speak with him about leaving.
"Well, maybe just a sip..." (Bronze)
At the bar in the casino you can and have to pick up the Marillo de Oro. Have Manny drink it.
"We are all citizens of the same nation, and our king rides a pale horse." (Bronze)
Ask Chowchilla Charlie for a passport. He is in the roulette room in the casino.
"YOU'RE NOT EVEN LISTENING TO ME!!!" (Bronze)
Lupe is the door greater at Manny's casino. She will tell you about her new organizational system, but not go into detail. Ask her about it, and insist that you want to hear about it.
"It shone, pale as bone..." (Bronze)
You can see the moon above the dock where Velasco hangs out. Push square while looking at it to have Manny recite a sweet poem.
"Consider it an homage." (Silver)
In the Blue Casket have Manny get on the mic and make some poetry. When you're done ask Olivia to do some. She will copy whatever you did.
"We're straight stingers, you know?" (Bronze)
Talk to the sea bees about forming a union.
"Here, let me hold that metal detector for you while you cry..." (Bronze)
Carla is the one who checks passengers before they board the blimp in Rubacava. Drink the Marillo de Oro you got from Manny's casino and then try to go up the elevator there. You will be taken to the back room. While back there your goal is to get the metal detector from her. In order to get this trophy never choose the last dialogue choice dealing with the metal detector until she is crying and no longer telling the story.
"Manny, we've given up. All of us." (Bronze)
Membrillo is the local mortician in Rubacava. Ask him why he still hangs around.
"Come to see how the big boys play, eh Manny?"(Bronze)
Enter Maximino's VIP lounge. On the screen where you can see Nick there is a large red doorway in the background. Enter it and talk with Maximino.
"So, sorry, but I don't do... 'odd jobs.'" (Bronze)
In Maximino's VIP lounge speak with Nick and try to convince him you need a lawyer.
"Oh, yeah, I could take you down..." (Bronze)
This can only be gotten while Glottis is getting drunk in the VIP lounge, but before you get into the wine cellar. Aitor the green demon who works in the lounge will be waiting by the elevator to the wine cellar sleeping. Talk to him and exhaust all of his dialogue options.
"Oh Rusty Anchor" (Bronze)
Once you find Lola sprouted at the lighthouse, Manny receives a card with a tongue on it. Go back to the casino and give it to Lupe. She will then hand over a piece of paper that says rusty anchor on it. Before you rush out and give it to Toto, go downstairs and show it to Glottis. He will then serenade you with a sweet melody.
"ME, ME, ME-ME-ME!" (Bronze)
Once you have Nick get Terry out of jail he will be leading a chant where he originally was near the lighthouse. He will start, and then the bees follow. You need to interact and follow as well. If you do it too early or too late you will be chastised for not being in-time. Once you get far enough in the chant the bees will start to chant about Manny. When the entire chant is over it will begin to repeat. When you stop the trophy will be awarded.
Year 2 (Silver)
This is automatically awarded at the end of year 2.
"I wasn't always this color!" (Bronze)
When you meet Chepito for the first time ask him how long he's been under the sea.
*sniff* *sniff* (Bronze)
When Manny wakes up after being punched in the face by Domino there will be a cage of angels in front of him. Be mean to them until they cry.
"Save your breath..." (Bronze)
Meche thinks you're working for Domino. Have Manny try to explain the whole situation to her.
"Okay, how much of this haven't you figured out, Calavera?" (Silver)
Go into Domino's office and have him explain what his racket is.
"IT'S A BUST-ALL!" (Bronze)
Before you trade anything with Chepito exhaust all of his dialogue options.
"Stop showing off for the girl!" (Bronze)
Manny will find himself on the octopus-submarine fighting Domino. Have him whip out his scythe and then proceed to run at Domino until you get the trophy.
Year 3 (Silver)
This is automatically awarded at the end of year 3.
"Happy trails, Captain." (Bronze)
Enter the waiting room to see Chepito walking around in a fountain. Speak with him.
"I could walk out of this world and not look back..." (Bronze)
In the room with Chepito have Manny try to walk down the tunnel.
"I'm getting out of here. This world's for suckers." (Bronze)
Let Bruno out of his casket.
"...so large." (Bronze)
This trophy is easy to miss. When Glottis falls down at the beginning of year 4 you will find him surrounded by smaller demons. Do not talk to Glottis! Make sure you talk to the little demons first and exhaust all of their dialogue. If you speak with Glottis first he will make a drawing on the wall and the little demons will move there and no longer have any available dialogue.
"Oh, Lola..." (Silver)
Upon your return to Rubacava climb up the lighthouse to where Lola was sprouted.
"THAT'S NOT FUNNY!" (Bronze)
Once you've frozen the lemonade and are walking towards the booby trapped Bone Wagon have Manny examine it. He will make a terrible joke and Glottis will get upset.
"Manuel! Is everything okay?" (Bronze)
In the Lost Souls Alliance HQ interact with the radio opposite where Eva is sitting.
Year 4 (Gold)
This is automatically awarded upon beating the game.
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