First things first, make sure that the difficulty is set to hard via the options menu. Once that's done, make sure you go to game modes, and go through Beatings with Bass. Doing it in any other mode will not give you the achievement. From there, select the Penthouse for your arena, and Sittin Sidewayz as your theme.
With Beatings with Bass, you lose the ability to scratch, only being able to use the environment when the Bass hits. For your opponent, choose someone named Dae Dae, as he will pretty much do nothing except attack you. Dae Dae will unlock over the course of Build a Label, so you must progress through a bit before you should try this achievement.
You will not be able to do anything at all, except for reversing an attack. To reverse an attack, hold , and press either up or down on the , right before the attack hits you. All attacks are either low or high, hit up if you need to block a high attack, or down for a low attack. Go right away to the window, and make sure it is damaged. Once you do, wait for him to attack, and counter. It may take a few times to get, but once you reverse it, you can grab him. After grabbing him, just throw him right out of the window for this achievement.