I’m not making rules, I’m making observations. And I was intentional about limiting them to pop music, where youth has held sway for roughly 75 years. I was also careful to say that anyone is free to weigh in on anything.Can people in their 40s and 50s, without being labeled ridiculous and arrogant, discuss legacies of contemporary movies? TV? Books? Art? Fashion? Is everyone older than their 20s discussing the latest Marvel TV show on this board ridiculous and arrogant and pathetic for expressing their opinion about where it falls within the canon of other Marvel projects? What is particularly different about music or the "legacy of songs"? This rule you've made seems highly specific and inconsistent when applied to music alone, but also any other form of art.
If you want to say, "Bill Simmons is ridiculous and arrogant for discussing Taylor Swift's legacy songs because he has very little depth of understanding about music beyond Pearl Jam and U2," that's a fair argument that I probably agree with. This is not his wheelhouse. Frankly, I don't know enough specifically about Klosterman to say what his opinion means on anything. But you're making a very different argument, that age and sex somehow convey special knowledge unto a person, and no matter how much you listen to an artist or are a fan of that artist, or even if you're just a highly engaged, interested observer, you are "pathetic" for even thinking you can discuss the topic. That's a pretty broad statement that, I think, blindly parroting dissuades people from staying in touch with modern music and having interesting discussions about it.
But it’s one thing for you and me to discuss pop music on a message board or over coffee. In those spaces, we can agree or disagree about anything and hopefully have a mutually enlightening, or at least interesting and intelligent conversation. But neither of us is reaching an audience of whatever the enormous audience is for Simmons’s podcast. Those kinds of conversations become categorically different—though in either context, I’d find it really silly for someone to ask what I think Taylor Swift’s legacy song(s) will be. So I’m not questioning their right, but I am saying that it’s dumb for them to entertain an attempt at gauging the legacy of an artist who’s in all likelihood barely at the midpoint of her career (and who may not have even written her legacy songs yet) with a large and devoted fan base most of whom are well outside the demographic of middle-aged white dudes—white guys who have every right to have any opinion on Taylor Swift that they choose—but who also risk being giggled at when they shoot for the wobbly posterity of pop music icons who are close to two decades younger than they are.
Legacies are the long shadow of an artist’s career. It’s one thing for me to say, “I’m an older guy but I love Billie Eilish’s music” or “I think Ed Sheeran is to popular music what Chuck Klosterman is to pop culture journalism—as deep as a puddle and about as interesting,” but another to say that “Ocean Eyes” will be the defining song of Eilish’s career. The first are comments about my taste, the second makes a wager on history. I have no issue with anyone of any age, gender, race, or creed telling me that I’m an idiot for hating Ed Sheeran’s music or Klosterman’s writing (except for the obvious fact that they would be wrong, of course), or that if I dig Elliott Smith, I may want to check Beabadoobee (and you all should—she’s wonderful), but I have little interest in listening to someone close to my own age who agrees with me about Sheeran and wants to tell me why his fame will be so fleeting he’ll make Andy Gibb look like Nick Drake. It’s not our call. And that’s not a rule—it’s simply the way pop music legacies have worked since teenagers and other young people became the most ravenous consumers of music. So we’re all free to yap about whatever we please—I certainly wouldn’t have been a member here for more than 20 years if I thought otherwise.