This achievement is easily done in local co-op in either scavenger hunt or tic-tac-toe using a second controler. There will be power boxes in the levels which you can pull a lever on upon which a timer will start.
As soon as the timer is done it will spawn a random item, which can be either the running shoes (with which you need to run 2.000 metres, "Humiliating hat attck" which is a traffic cone, "Shoe glue attack", or the one you want for this achievement, the "Horse mask attack".
After obtaining it, just walk up to the second player and give it to him to get the achievement-.