Convince an Orque Guard you are an Orque
Story related trophy. You will start the game in the Orque P.O.W. Camp, armed only with a potato peeler. After a series of fights, you'll encounter three P.O.W.s to talk to who give you several quests that must be completed in order to get this trophy. Make sure that you talk to all three for the entire strategy.
Death of a Penguin
Kill the Evil Nun
Story related trophy. In order to confront the Evil Nun, you will have to first gain access to the Sanctuary which will require you to be granted access by the Monk of Admittance.
See all 20 of Madames Primp's Outfits NOTE: This trophy is missable.
Visit Madame Primp's Brothel in Strumfuquel. She will ask for proof that you're a serviceman, which you can get by finding dog tags in the Jungle and showing them to her. For $1 per visit she will offer five sets of four costumes each, for a total of 20 costumes. Madame Primp will rotate through each of the five sets in order. As long as you do not open the chest in her room, you can continue through the list until you've seen all 20. If you open the chest however, she will attack you, preventing you from seeing all of her outfits. The list is below:
Get an Engineering Degree
On the railroad tracks west of Strumfuquel you will find a stopped train on a blocked track. You'll assist a conductor to clear the blockages with a series of increasingly convoluted missions by bringing dangerous materials to an engineer. The first conductor will give you the mission, "Nitro Run" requires you to carry the Nitroglycerin to the engineer without attacking enemies or being hit. The second mission, "Dynamite Shuffle" gives you a limited time to reach the engineer before it explodes. Use the nearby Outhouse to bypass the path and give you enough time to reach the engineer. The third mission, "Acid Reflux" requires you to carry acid to the engineer while being continuously damaged. Increase your acid resistance through armor or potions to ensure you aren't dissolved. Once all three missions are complete, keep following the tracks to find a fourth conductor standing at the end of the line near a large rock wall. Talk to the conductor, and it will trigger a cutscene where Deathspank goes to school, gets his Engineering Degree, and the trophy! Incidentally, the hole that is blown in the rock face leads to a "hidden" area containing Orques sporting Hothead attire and the names of their staff. This large collection of Hothead staffers is also a great place to farm the Dispenser of Justice trophy. See that trophy description for details.
Raise Your Mast
Go Sailing in a Pirate Ship
Travel to Scurvyville and speak to Captain Taint. Ask him about his ship, and he will give you missions to find three things that he needs before you can borrow it.
Learn to Speak Japanese
NOTE: This trophy is missable. See the To Serve Man trophy for details.
Dispenser of Justice
Kill 3000 enemies
The description of this trophy is somewhat misleading. Not only do enemies count towards your total, but also animals such as chickens or rabbits, so take advantage of their low hit points as you go through the game to rack up some easy kills. This trophy will come with time, but you will likely not have scored enough kills by the end of the game to receive the trophy. An easy place to farm the remainder of your total is at the "secret" cave at the end of the railroad tracks that you discover while earning the Well Educated trophy. There are 45-50 Orques with extremely low hitpoints that you can kill in under a minute. Exit the cave and walk a sufficient distance away (following the tracks as far as the opening in the fence to the south should be sufficient) turn around and return to the cave, and they will respawn, allowing you to kill them again. Use the Book-o-Stats in your inventory to keep track of your progress towards 3000 kills.
To Serve Man
Story related trophy. Once you reach Wortten's Factory, gaining access to the famous chef will be no easy feat.
A True Hero
Reach Level 20
This will come through regular play, likely before you complete the game. If for whatever reason you don't reach level 20 before the end of the game, you can select Continue from the main menu to load your last checkpoint, then continue to rack up experience. There are more than enough side quests and enemies to earn experience from to make up the difference.
Discover all 44 Teleporting Outhouses
There are 44 Outhouses in the game that you can travel between, 43 of which appear on the map and the 44th you'll gain access to at the end of the game through an item. See the map below for the names and locations of all of the Outhouses.
Kill Santa Claus
Show Santa the true meaning of Christmas by giving him the gift of Justice!
A Tale of Two Endings
Watch Both Game Endings
At the end of the game, you're asked to make a difficult choice. Once you've decided and played out the ending you want, select Continue Game from the start menu. You will return to the last checkpoint before the end, allowing you to make the other choice and get both endings in a single playthrough.