Which pineapple juice to use?
For your mixed drinks you can use canned pineapple juice and have excellent results. I recommend Dole pineapple juice as it is 100% juice, widely available, and not from concentrate. The 6 packs of 6 oz cans are very handy if you don't need all that much at a time (which is most of the time for me). You won't have to try to keep opened cans fresh (just pound what remains). Dole does make a 46 oz can that is great if you need a lot of pineapple juice.
Trader Joes's has a pineapple juice in larger cans. I tried it hoping it would be even better or fresher than Dole but I was disappointed. It was pretty thin. Also beware of some brands (especially Hispanic brands) that add sugar or other ingredients. Stay away from these - you want 100% pure pineapple juice for the drink recipes on this site.
You can try to juice a fresh pineapple if you wish but it is quite a mess. The juice is great but for me not worth the effort.
Hot to squeeze your own pineapple juice
I use a hand citrus press to make pineapple juice. My stand citrus press will clog on the flesh too much.
Peel and core a whole pineapple. Cut it into chunks suitable for your hand press. Press each chunk into a bowl. This is going to make a mess, so use a large bowl and try to keep the press low in the bowl. Press the whole pineapple before using the juice, as some parts of the pineapple may be more ripe than other parts. When you are done, taste the juice. If the pineapple was not quite ripe enough, sweeten with simple syrup. You can strain the juice if you choose, but I never do. A pineapple will yield about a pint of juice.
Drinks with pineapple juice
Pineapple juice is used in a huge variety of drink recipes most of which are Tiki, tropical, or Caribbean style drinks. You will also find pineapple juice in some classic cocktails such as the Algonquin.
But the most common combination you will see is rum and pineapple juice - they just seem to have an affinity for each other (and it helps that they are both plentiful in a lot of the same places in the world). Pineapple juice also has a curious affinity for chocolate - more specifically creme de cacao. Some Tiki drinks have a small amount of creme de cacao along with the base spirits and pineapple juice.
As with all juices you want to shake pineapple juice drinks (or mix with a stand mixer). Unlike other juices pineapple juice will develop a frothy head when shaken. This is quite desirable and leads to an attractive drink.
Do you enjoy your pineapple juice with base spirits other than rum? Let's hear about it...