Gotta respectfully disagree with ya.
Why only the last four years? I think the ad was more powerful because it emphasized the
timeless cultural ubiquity of telephone communication over the last SEVENTY years, from the past slowly up to the present. The entertainment icons were fun, and appropriate to the Oscars timeslot in which the ad ran. (And of course, the phrase "Hello" was used quite cleverly to echo the fact that this was the iPhone's first introductory advertising to the public. So the iPhone saying "Hello" to us is the perfect punctuation on this ad.)
I'd say "The Anchorman," "Zoolander," and "The Incredibles" could be considered teen-friendly endorsements.
Steve Jobs' Macworld Keynote was really the first "ad" for the iPhone. All the product features were covered then in great detail. The iPhone's target audience is sophisticated and tech-savvy, and they all know where to get the technical details online anytime they want them. So this frees Apple to use the iPhone's official advertising in a more unique, impactful, fun, image-building way... rather than listing a bunch of old bullet points about its features
yet again. That would be (by Apple's standards) boooooooring.