My theory is that the way to keep pop culture jokes from getting annoying is to tie them into the personalities of the characters who are making them. I don't want to make myself look better than the professionals or anything, but I draw a comic strip for fun called "Forever 16", which focuses almost exclusively on pop culture humor. Rather than just going "Hey, remember this?", I have my characters react to these cultural events in a way that feels natural for them based on their personalities.
My main character, Joel, is an innovative thinker who's always got an idea for how things should be done, so when he goes to see G.I. Joe: The Rise of Cobra and decides he doesn't like it, he gets out his old G.I. Joe toys from when he was a kid and videotapes his own movie. His younger sister, Katy, has an opinion that's very easily swayed by whatever's popular at the given moment, so when she tears down her "Wizards of Waverly Place" posters and instead wallpapers her room with "Sonny With a Chance" memorabilia, her conscience manifests itself in the form of Hannah Montana to tell her that she's a fickle victim of the Disney empire. Joel's best friend Aaron is a resourceful guy who looks to take advantage of any opportunity laid before him, so when Cash for Clunkers rolls around and he wants a new car even though the one he has is perfectly fine, he takes a baseball bat to it in order to "clunkify" it enough for it to qualify for a trade-in.
To me, that's pop culture humor done right. It shouldn't be the punchline of the joke, it should be the opener.