This was great! The part where Gaylord says "You really think that physical harm an-" and then Fart punches him was especially hillarious! :D

...why do I have the feeling the I Like Trains kid said his speech on purpose?

I liked everything except the D.E.B. fail. It was so sad it almost gave me nightmares.

Love how the stickman goes "waaa" in the options "Leap" and "Bridge".

ENTIRE WALKTHROUGH

Here's a walkthrough for all the medals:

LOL BRAWL REFERENCE: Once you get the cake, choose the drill. Then use the crowbar to get down. When the police chase you, click left first, and near the wall, click left from the door. You will slip, get a Message from PBU, and earn the medal.
LEGAL ENDING: Once you get the cake, choose the cellphone. Call your friend, who will lend you a hand. Characters are switched from Henry to Fletcher Reede. Use Fletcher to bring out the disguise bag from the set of Henry's items, and FR will ask "How did he tie the knot from the outside of the bag?!" Eventually, the judge will approve this, and Henry is freed the Legal way.
BADASS ENDING: Repeat the process of the Brawl Reference, but this time instead of slipping choose the wall. Henry will climb up, avoiding the guard. The master guard will come at you, once it says 'Get Ready' start clicking randomly. Henry will avoid all of the Master Guard's gun shots, as well as grabbing one shot to break the MG's gun in half. Henry will escape easily, since the other guards are scared now.
SNEAKY ENDING: Once you get the cake, choose the file. Use it on the cell door. Click left and right respectively, and Henry will knock down both guards. Hide in the door, then pick the chair. Walk through the right of the pipe, and Henry will end up on the top of the cell. Choose the plungers and escape.
DONUT WANT!: Nab the Drill from the Cake. When you come down there, click the Bagel(Funny how its a bagel when the medal is donut want) quickly. Then choose the Opaciator. Click Skip, and Quickly, Click the Same Donut. When you see a box, click it. Congrats, you got the Medal.
LOTS OF EFFORT: Since you already got the brawl and donut medals, you have 2 FAILs. Here is a list of more things to do:
-Repeat Legal ending, but DON'T choose the disguise bag. 1 FAIL achieved!
-Repeat Badass ending, but do the escaping from the Guards backwards(except the brawl reference part). Also Waiting gives you some fails as well. Doing this will give you 4 more FAILs.
-Repeat Sneaky ending, but do things backwards(not clicking when the guards come, pack of grenades, etc). The window helps too. Also use everything but the plungers at the ceiling as well. This gives you 8 FAILs.
-Choose the RL, Teleporter(which never did work) and the NrG drink for 3 more FAILs and a medal.
Secret Medal/BRAAAGGGHH!!: Repeat Sneaky ending EXACTLY how I told you. Watch the entire credits, then click the sun. This will throw in an extra SHOOP DA WOOP as well as the medal.

Hope it was useful, and please don't ban or terminate me!

This song is so good, it appears on TypingWeb.