The problem is that kicking barrels is not a main mechanic of the game, so it is not refined enough for such a massive requirement.
If you don't have godly mechanical skill, this achievement can seem insane if not impossible.

But it's still possible through sheer determination, though with advice from others it became easier, I've made this guide to share that advice.

Score as many points as you can the normal way without reaching 100 kicks

Buy some drinks and toss them into the pit where the hoop is located, doesn't matter what.

Stand at the bottom of the hoop area, from here you will get all the points you need, no matter how long it takes.

Jump and toss your mug upwards at the same time, momentum from the jump carries over into the mug toss, it make take a few tries for you to get the timing down, eventually you'll be able to do this rapidly.

Mugs do not count as kicks and give you 1 point every time it passes through the hoop from either side, on average it may give you 1 or 2 points with a single through, sometimes 3 points or more.
The most I've gotten with a single throw is 9 points, though it only happened once.

I accomplished this alone, but doing it with a group will obviously be faster if you can find some people willing to stick around doing nothing but tossing mugs for a few hours.