In the main lobby area, press and hold RB. Use the left stick to select an "emotion" and keep holding the stick and then let go of RB.
You don't need to let the animation finish, so quickly hold RB and then select another one.
I'm pretty sure you can keep doing the same one over and over but I just spammed each option on the wheel till I got back to the first one I did. Did several rotations till this achievement unlocked.