Not everyone has the insane mechanical skill that the achievement "If Only I Got Paid For This" takes to get the intended way. So this is a guide on how to get it through sheer determination.
How to Obtain If Only I Got Paid For This Achievement
What's So Bad About This Achievement?
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.
Doing It the Hard Way
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.
Aim upwards at the hoop and jump as you throw your mug.
Done right this will give your mug enough momentum to pass through the hoop from the bottom, if not go over and pass through it coming back down.
On average it may give you 1 or 2 points with a single through, sometimes 3 points.
The most I've gotten with a single throw is 9 points, though it only happened once.