So simple, but lots of people my age don't know how to make it. Fresh whipped cream is one of life's simple joys. Buy heavy whipping cream, as fresh as you can get it, and ideally the ingredients should say "Cream" and nothing else.
Use 8oz cream if you've having a few people over for waffles or sunday brunch, more (1 pint) if you're going to be serving lots of ice cream or dessert.
Pour 8 or 16 oz cream into chilled metal or glass bowl. Add 1/2 tsp vanilla extract per 8oz cream and 1-2 tbsp per 8oz cream. Grab a hand held mixer and start beating at the lowest speed to start, slowly increasing speed as the bubbles get smaller and the mixture get frothier. Beat until you hit stiff peaks, but not any further, or you'll get a lumpy mixture with tiny butter granules in it. Stiff peaks are when you can lift the beaters out of the cream and the cream sticks straight up, and flops over very little.