To get this achievement you must complete challenges 6, 36, 66, 96, 126, 156, 186, 198, 216, 228, 240, 252, 264, 276, 288, and 294.
I suggest for the more difficult ones, is to grab the shirt you have on and put the meat under your right thumb on the outside (the side of the shirt people can see) and place the four buttons of the controller on the inside of the shirt (the side of the shirt that faces your body) and move your hand left and right as fast as you can. When the bar is at the correct height pull the left trigger down and you should pass it.
Posted video of me performing the most difficult test your might with ease.
Another suggestion recommended by TA user "xC H E E Z U Sx"
Place your right thumb in the middle of all the buttons and mash. You should be able to cover all four buttons.