Photo: Larry Busacca (Getty Images for NARAS)

A good cover letter apparently should open with an anecdote that displays grit and character and perseverance; it should not just come right out and beg for it. Before I had the slightest idea about any of this, I’d lead with a story about interviewing actor and Deadspin commenter Jon Hamm as a mostly untrained college reporter, taking care to mention that I didn’t have credentials at PNC Park but still pogoed between gates and made phone calls and managed to get into the press pool.

It wasn’t about pestering my way into a story, of course. I never even ended up seeing Disney’s sorta-baseball movie Million Dollar Arm, despite writing several hundred words about its background. It was about getting close to the star of a favorite TV show, right there in the city where I live, and maybe doing some investigative bulge reporting. After the brief period of questioning was over, I saw some local news guy go in for a selfie with Hamm and took it as my cue to do the same. “The lighting isn’t even that good,” the local movie reporter of record scoffed from the sidelines, completely correct and obviously jealous.

None of that last paragraph ever made it into the cover letters, even if it was far more true to my approach to reporting at the time. There’s the part of me that’s deeply ashamed of all of this now, and can even see where it might be disqualifying. But there’s also the part that feels like, in that moment when I leaned in for that underlit selfie, I’d already nailed down the endgame of becoming a successful pop culture journalist. I just hadn’t figured out how to hide the grift yet, or figured out what side of it I was on.

You don’t have to look too hard to find culture writers at major publications posing for photos with celebrities they cover, sometimes even right there in their social media avatars. It’s an increasingly commonplace perk of the job, now, once previously thought to have been off-limits because it looked like getting too close to one’s subjects. It almost never means that, but the appearance is the thing. This isn’t just a thing for culture writers, either—it long ago became common among respected political reporters, who now feel comfortable snapping proof of themselves enjoying swanky dinners with their ghoulish subjects or sobbing through a letter of encouragement from Hillary Clinton.

It’s a circular game in many respects, in ways that are new and others that aren’t. Critics tend to use kid gloves on the most popular artists, at least provided those artists are not named either Ed Sheeran or Justin Timberlake. The possibility of those artists retweeting your coverage will always present itself, providing an instant boost to your site’s traffic that can be more reliable than anything it might manage from its own social media account. This is true to some extent with artists at any level; I’ve heard conversations play out regarding the best time to post a profile so that a mid-level artist might be online to read and retweet it. When an industry is dying, the desperation becomes a little more apparent. The ship sank some time ago, and this is the lifeboat we’re clinging to.

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The one case in which coverage might shift or sharply take a turn in the public consciousness is when an artist does something unconscionable, or just becomes someone you wouldn’t really want to hang out with anymore. There’s nothing favorable about a popular artist pivoting to MAGA brain-rot, rambling on about how slavery was a choice, or cozying up to a union-busting goon, of course, but music coverage was once able to separate problematic artists from their less-compromised art. This isn’t easy. As listeners and critics, it is easy to project our own values onto these artists, and tempting to believe that these unfathomably wealthy types trade in universal feeling and are maybe even nice people besides. Right up to the point of no return—for example Kanye doubling-down on his support of Donald Trump this spring—there are a number of simple and variously effective rationalizations near at hand. Maybe he’s going through something. Maybe he’ll delete the tweets and renounce all of this. He’s unwell. The free trip to Wyoming for the record release doesn’t hurt.

There are reasons why a critic or journalist or fan might want to be close to an artist—they’re good at a thing you care about, their lifestyle requires fewer compromises than yours, they’re often better looking than most other people. The Almost Famous travelogue days of music journalism provide a sort of romantic template for how this relationship might work, even if it mostly exists today in a realm closer to Recovering From My Breakup In Joshua Tree And The Fairfield Inn & Suites. Objectivity is a lie, in criticism even more than elsewhere in journalism, but what about honesty? Seeing a writer pose with, say, Taylor Swift doesn’t invalidate their perspective, or even necessarily imply that having taken that selfie will color future coverage of said artist. But man if it isn’t hard to imagine how it could.

I think that people do know that this matters, but don’t quite know what to do with it. Some old barriers have dissolved to nothing in recent years—between fan and reporter, between artist and fan, between reporting and publicity. Even the way young writers talk about their favorite entertainers has shifted. It’s now increasingly common for people who cover popular artists to talk about them on social media as they would best friends, crushes, or someone we’d allow to stab us with a sword. I’m not absolved of this either; to save you a search, I’ve referred to Spoon frontman Britt Daniel as my father and maybe more than a father on multiple occasions. Whether we do this because these people seem far outside of our own circles—not just stars like Jon Hamm but characters like Don Draper—or just to honor adolescent fandom is hard to say. Fandom has never been easy to parse. But it is strange to see how this perspective has began to translate to once-stuffy critics’ circles.

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There is, still, an old guard of journalism which preaches suppressing biases and trauma and qualities otherwise associated with being human in favor of reporting the damn news. There are other people covering this stuff who seem to live authentically advertorial lives. I think the sweet spot is somewhere in the middle—Caity Weaver, formerly of Gawker and GQ and current NY Times writer, has sort of boiled it down to an art. Her widely read profiles sometimes refer to subjects as best friends but also use that level of comfort to mine interesting and previously unknown information about that person, which she then passes on to the people she is actually serving—the people reading the story. This can’t be easy, but it does illustrate how a perspective that takes both editorial distance and human fan-feelings into account might work—something a bit more human than the old, formal relationship, but which stops short of pure advocacy.

This doesn’t change that it’s all just an ongoing sweepstakes for many. You often see things about how some writers feel lucky for the opportunity after a high-profile interview, despite the entire transaction having been orchestrated by publicists, editors, and other parties outside of the artist’s control to remove any variable as chance-y as luck. Everyone’s just doing their jobs, until suddenly they’re not.

A professor once asked me and some classmates a version of this important question for anyone in journalism: Do you like to write or do you like music? Which do you need more? You can tell who’s thought about it, and who has thought more about whether the lighting looks OK.