I unlocked this from The Arcades level called Fan Service. All you have to do is just throw the boxes up over 3 line up fans. I got this the first try without even knowing there was an achievement for less than a minute so figured I'd share this easy method to get this achi done with little to no fuss....
I even missed a truck about 7 times too so I don't even think it's too tight for time.
I unlocked the level Fan Service after finishing the Packmore River, or the frogger inspired level...