If you choose to live your life by the Gospel According to Will Ferrell, you must first learn how to do it correctly. Quoting pop culture is a useful tool because the jokes are already written, they are already accepted as being funny, and referencing pop culture lets people know that you are up on the latest trends. The key word there is latest, though, which brings me to my first point.
Don't use outdated quotes
Sure, the Austin Powers movies were very humorous and quoteworthy" 7 years ago. It was standard practice to employ such Austin Powers quotes as "Groovy, baby" and "Get in my belly." They were comical and well-known, so it was OK to use them. Nowadays, the only people who still use Austin Powers quotes already have a spot reserved for them in Hell next to the baby kitten rapists. If you are going to reference pop culture, make sure that your source is current and not overused. Of course, there are exceptions to this rule. Timeless movies, such as Caddyshack and Billy Madison, are always quoteworthy. Feel free to quote Caddyshack whenever you want, especially when Journey's "Any Way You Want It" comes on. (So what? So let's dance!)
On the flip side, there are certain pop culture quotes that should not be repeated, simply because you can only make them worn out and not funny, the opposite of what you are trying to do. I call this the "I'm Rick James, Bitch" rule. If you find yourself saying a quote and then having two or more people repeat it immediately after you, it probably falls under this category. You'd be wise to avoid these quotes.
Don't use obscure quotes
A key aspect to quoting pop culture is that what you are referencing does indeed have to be popular. You don't want to find yourself explaining every "Arrested Development" quote that you throw out there. For instance, if you quote some obscure movie and you fail to elicit a laugh, just move on. There is no need to have to go through setting up a whole scene and explaining who certain characters are just to get an easy laugh. By the time you're done with the setup, no one will care anymore and you'll just look like a heaping bag of Santorum.
If, by some chance, your quote gets a laugh AND is seen as original, then you have hit the jackpot my friend. Feel free to wallow in your own crapulence. Just make sure that if someone later identifies the source of your quote and reveals you to be a big fat phony, casually say, "Oh, so THAT'S where I heard it" " and then walk away. Stay far away from these people because they generally tend to be big douche bags, which conveniently segues to my next point.
Don't correct other people's quotes
People who correct other people's quotes just plain fucking suck. These nerds spend countless hours memorizing quotes just to bust balls when someone else misquotes. These jerkoffs are the bane of the Pop Culture Quoter's existence, simply because they are there to tell you when you're wrong, so avoid them at all costs. Even though these guys can ruin the comedic mood, they only do it because deep down they know that they are the real losers, namely because they asphyxiate themselves with a belt while masturbating to Japanimation. And now that you have that savory image in your mind, let's move along to my next point"
Don't overuse quotes
Using quotes can make you appear humorous, but you must be careful not to be known as "that guy who always quotes stuff." Everyone knows at least one of these guys, the dude that always says, in his crappiest Ron Burgundy impression, "I'm kind of a big deal" to every person he meets. No, you're not. You suck, and are ruining it for the rest of us who appropriately quote pop culture. Unlike drinking, you must be careful to practice moderation when quoting. My simple rule to make sure I don't overquote is that after I say a line, I either wait two minutes or hear two other people use a quote before I quote again. This way, no one can accuse you of overquoting because either enough time has passed since your last quote or because other people are actively quoting as well.
So there you have it, folks. Simply follow these guidelines and you'll be well on your way to comedic success, albeit pirated comedic success. But hey, that's better than no success at all, right? And if you notice someone breaking one of these rules, just refer them to this guide. If they continue to break the rules, just give them a swift shot to the solar plexus. Works like a charm.