Basically all you have to play/get is:
Get a private dance at the men's club
Rob a store
Go to the shooting range (can play by yourself)
You do not have to win at golf, tennis, darts, arm wrestling or shooting, you just have to simply play and finish the task.
If you have done all of these and have not got he trophy (I had this problem) you have to get a chest tattoo. An arm, leg or any tattoo other than chest won't work.