Putting a Lid on Crime - While fighting against the giant five-headed planarian worm in the prologue pick up a trash can lid (There's one next to the car) and use it to block whatever it is its throwing at you.

You Should See the Tequila Bottle - Blow up the giant five-headed planarian worm in the prologue

Watch - Obtain the Watch

Office Intern - Complete the task list in Sam & Max's office by making Sam coffee, throwing weapons at the dartboard, shooting three roaches in the closet, putting a corn dog on a stick and then cooking it in the microwave and giving it to Max, punch the clown directly in the nose 5 times. If you somehow manage to struggle getting this achievement I recommend you delete system 32.

Dial M For Murder Hornets - Open up the filing cabinet that is titled "Topical Humor (1919-1958)" and then flying devil pests will swarm out.

Flint Paper - Sam hints that the paper cup is good for listening in on conversations, so in order to acquire the Flint Paper achievement (non-violently) you must hold the cup against the wall behind Max, beside the file drawers and right next to the cardboard box on top of it, with the hole of the cup facing towards yourself. With the bottom of the cup pressed against the wall, move your ear inside the cup to listen in on Flint Paper's dialogue from across the wall. You can also hear another unique dialogue when listening from the door next to Sam and Max's office.

The Extra Inch Award - For The Extra Inch Award, you just need to find all the interactable curios within the office that triggers dialogue from Sam and Max which are:
- The space rock on the desk
- Dr Dills can
- Paper cup
- Opening all the file drawers (or just the ones on the right)
- Finding the rat hole behind the moveable cardboard box on top of the file drawers
- Scrumpos bag
- Aqua bear tank
- All answering machine recordings
- Listening to the phone
- Opening the window
- Turning on the TV

Credit to Uncle Graggy in the comments for helping me find flint paper and the extra inch award :D

Not Entirely Pointless - Pop all of the balloons in the "Pointy Throwing Thing" section with darts in the Voyage of Pain.

This Hurt Me More Than It Hurt You - Don't take any damage in the Voyage of Pain

Helium Hoarder - Collect all of the balloons in the Voyage of Pain

It's Raining Bombs (Hallelujiah?) - Make 10 Baskets in the BasketBombs portion of the Voyage of Pain.

Voyage of the DANG! - Earn an A in the Voyage of Pain (Just try not to get hit and get a good time?)

Putting the 'A' in "Asplode" - Earn an A in Bombs Away (Try not to ♥♥♥♥ up!)

Bullets Ain't Cheap, Y'Know - Earn an A in the Circle of Carnage (Shoot as many targets as you can and try not to get shot back)

Neutron Neutralizer - Defuse Teddy Tocks's Neutron Scrambler (1st Boss)

Act I, Player 0 - Complete first traunch of Freelance Police Academy courses.

Bunts are For Losers - Hit 10 Home Runs in one game of Fizzball (You will need to find your sweet spot)

A Clue? Gesundheit! - Earn an A in Get a clue (Just go fast lol)

Most Valuable Fizzer - Earn an A in Fizzball (Try to be as accurate as you can with your hits and score)

Love Machine - Earn an A in the Tunnel of Tough Love (Punch every single one of them damned clowns)

Clean Up in Aisle 666 - Banish Demon Max by throwing 3 hoops at him and hitting him with the dagger. (2nd Boss)

Act II - The Actening - Complete the second wave of Freelance Police Academy Courses.

High Anxiety - Collect all of the balloons and wings in the No Fun House

Rat Whacker - Hit five or more rats with a mallet in the No Fun House when you get to the whack an Aquabear machine thing

Hoverachiever - Earn an A in the No Fun House (Go through it fast)

Nacho Dust Buster - Avoid all of the Scrumpo Grenades that Max throws at you in Sky Patrol (Throw your balloons at the Scrumpos to destroy it)

Grandmaster Splash - Earn an A in Sky Patrol (Hit those targets bro)

Streak Freak - Get Jeff to perform 5 tricks consecutively

Whisper Winner - Train Jeff (Hit all of the tricks with some time to spare)

Pomp and Aquabears - Complete all of the Freelance Police Academy courses

Found Puddle - Use Max to sniff out the puddles that appear after the Aquabears kidnap Sam.

Shotgun! - Blast five or more Aquabears while sailing through the Nanoverse

Disco Ninja Aquabear Suit - Sneak into the Aquabear Meeting

Taste the Prismatic Projection - Feed Max every variety of the icky blobs floating around the ship

Spoke to DJ - Talk to DJ by pressing trigger on him

Spoke to Techie - Talk to Techie by pressing trigger on him

From Hell's Spleen - Shoot Cap'n Aquabear off the Desoto

Takin' it Queasy - Climb out onto the crane

The Freelance Student has become the Freelance Master - Put an end to the menace Capn' Aquabear

CONGRATULATIONS! - Graduate from the Freelance Police Academy

Sequel Bait, or Just Plain Bait? - Listen to the tiny impotent screams of the vanquished Capn' Aquabear when handed the souvenir

VR Maimed the Radio Star - Listen to the radio in the main menu until it does a full loop

Lumpy ♥♥♥ Laude - Earn an A in all 9 Freelance Police Academy Training Grounds