Grand Theft Auto IV

The easiest way to play this, is to face Michelle or Kate. They're terrible players. Facing Packie, Roman and Jacob will be next to impossible for a new player.

The rules of pool are simple enough
The object of the game, is to sink all of your balls, followed the 8 ball, First. If you sink a striped ball first, you must only sink striped balls, and vice versa for solid colors.

You will foul if,
You hit an opposite coloured ball, first
You sink the cueball
You don't hit anything

You will loose the game if
Your opponent sinks all of there balls + the 8 ball
You sink the 8 ball before it is time
You sink the 8 ball, followed by the cue ball.

either you get this by luck or you spend a bit of time learning how to play on a x box 360 controller personally i got it by roman potting the 8ball in too early but if you do lose just keep trying until you get it

Invite a friend to play pool. Take him to the place and just play. This achievement is pretty easy seeing that you have unlimited tries to get it. It's easier to win on the turns where you break.

To unlock this achievement you need to beat a friend or girlfriend at pool.

This achievement can be quite luck-based or skill-based depending on the types of people you are playing with. Playing with Kate or Michelle is the easiest way to win a game of pool because they are not too good at it, however, Roman, Packie, and Little Jacob are pretty competitive to play with, Little Jacob being the hardest. If you are good at pool then play against the boys if you want to, if you are a new player you'll want to play with the girls. Sometimes, if you're lucky, they will accidentally score in the 8-ball giving you an easy win. You can try again and again as there is not a limit, so just keep trying to win a game or wait until your friend or girlfriend scores in the 8-ball

Here is a video guide.

Credit: GTA Series Videos