For this you have to build 5 blockades with Jack and hit all 5 green areas to get a "super awesome" rating. Put it on easy so the areas are larger and easier to hit.
Each super awesome barricade requires 5 planks, so stock up at that start of a level, by letting Jack collect and helping with another character.
Also it may be bugged, as I got 4 and ran out of wood halfway through the fifth so I restarted the level. Then I got the achievement on the first barricade after. So maybe they don't have to be in a row..
-Edit-
Try for this near the end of the game when your barricades have been upgraded. I got this at the start of the last level, as the are alot of windows&doors close together.