Like a handful of other people said, it depends on the author's motives. Mentioning it in passing is fine by me, but going into detail about what generation iPod/iPhone or whatever the character has is too much for me. For some reason, it peeves me a good amount. Jokes referring to pop culture doesn't bother me, either, because I do try to avoid name-dropping but my characters tend to make sarcastic jokes having something to do with the current times. Unless it's my newest story which is based in the late 90's, so those jokes/pop culture references will be outdated on purpose.
Really, though, I try to avoid name-dropping when it comes to my writing. I don't mind when others do it, but when the author is trying to force it on the reader, then it becomes a problem. I also don't like when it comes out of left field; as in the sudden name-drop or pop culture reference doesn't fit with the rest of the story. Some authors tend to give the readers the wrong impression when it comes to era because of the speech or characters or clothing, then suddenly:
SMARTPHONE. It's kind of like Bates Motel. I hate the fact that they use smartphones and current technology because everything else about the show feels old, like in the 60's or something.