Game Link : Here
Walkthrough (BaraTanken made it not me): Here
You will need to finish the game to understand how to get these medals as Im too lazy to do a complete walkthrough.....

Cozy Stage: After getting the disguise done and the box thrown at the bodyguard go back to the house take a sleeping pill out and press space several times to take it. After that go on stage as normal. You can also take a sleeping pill at any time.
Here It Comes: Beat the game like normal without lighting the rocket with the bodyguard's lighter or taking a sleeping pill.
Cozy Spacesuit: Take a sleeping pill, light the rocket and jump up near the door and press space to get in rather than just going on stage.
Sleep Is The Ally: Take a sleeping pill and light the rocket but do not get in, walk on stage like normal.
Too Much Rocketeering: Light the rocket but do not get in and do not take a sleeping pill. Walk out on the stage.
One Helluva Schaffer Entrance: Do not take a sleeping pill, light the rocket and get inside before it takes off.