FOR OUR CONSIDERATIONCraziness, friendliness, or insight: What do we want from a celebrity interview?

Prince: We’re all indentured servants. When I found out there were eight presidents before George Washington, I wanted to smack somebody. I wanted to know why I was taught otherwise.
Tavis Smiley: We’re indentured servants and we’ve got a black president now?
Prince: Well, I don’t vote. I don’t have nothing to do with it. I got no dog in that race.

—The Tavis Smiley Show, April 28th, 2009

Two years ago, Prince sat down with PBS talk-show host Tavis Smiley for a two-part interview, which I recorded and watched because, hey, it’s Prince. Even though Prince hasn’t done much as a musician to hold my interest lately—at least not in comparison to 20 years ago, when I was a devoted fan—the prospect of an intimate hourlong conversation between Prince and one of his friends was too tempting to pass up. With other interviewers, Prince tends to get defensive or reticent, but I figured with Smiley he’d be a little looser, and maybe reveal a little of what it’s like to hang out with Prince.

And to an extent, yes, The Tavis Smiley Show Prince interview did just that. Prince talked to Smiley about the conversations they’d had together—and with Cornel West—about some heavy topics, like the phenomenon of chemtrails, and the eight presidents before George Washington. And right around the time Prince insisted that the problem with American politics is that there’s no religion in it, I realized a couple of things. 1) Prince is kind of a crank. 2) Maybe having a friend interview a celebrity isn’t always such a grand idea. Because while there’s a good chance that other interviewers would be just as deferential to the pop star, there’s also a chance that they might hear Prince casually mention the pre-Washington presidents and say, “Wait… what?” (I assume Prince was referring to the people who presided over ...l Congress, but why would that minor historical fact alarm His Royal Badness so? I’ll never know, because Smiley didn’t ask.)

I think a lot about celebrity interviews because I conduct such interviews on a regular basis, and I invariably go through the same two-step process each time. Step one: “All right! I get to talk to Lester Q. Famousguy!” Step two: “Crap! I’ve got nothing to say to Lester Q. Famousguy!” Or more accurately: the worry is having nothing new to say. To prep for interviews I typically read a stack of articles about the subject, and inevitably discover that the most relevant questions have already been asked, over and over. What’s left are the intrusively personal questions that I don’t want to ask, and the dry, process-y questions (“How much research did you do for this role?”) that I find interesting, but I’m not sure anyone else does. At the least, I often get the feeling that the people I’m talking to are mildly confused as to why anyone would care about how they do their jobs.

What I believe we look for from any interview is some glimpse of who the subjects really are. Are they funny? Thoughtful? Political? Warm? What can they tell us about what it’s like to be on a movie set, or in a recording studio? Are they friends with other famous folk? Do they have any amazing insights into their own work, or are they show-up-and-work-from-the-gut types? Do they have anything to say that would surprise us, or entertain us, or make us think about them in a new way?

But how to extract that kind of information? Earlier this year, Esquire writer Chris Jones wrote a blog post helpfully detailing his methods, while bitching that the more accomplished a person is, the harder they are to cover. (In response, Slate’s Tom Scocca wrote a post mocking Jones for not taking his own advice and almost exclusively interviewing bland, reticent big shots.) And last week, the Internet had some fun with Edith Zimmerman’s GQ profile of Captain America star Chris Evans, which reverts to the age-old “OMG I’m sitting across from the sexiest person alive!” method of covering the stars. Both Zimmerman and Jones seem to be saying that there’s a level of perfection—be it talent or physical beauty—that stymies writers, leaving them with no choice but to spout giddy superlatives. But they also realize that’s the business. Pretty people sell magazines, so writers better find a way to fill the pages next to those glossy photos.

And don’t think celebrities don’t know their value to interviewers. Baseball legend Joe DiMaggio was a prickly one about talking to reporters—especially late in his life—because he knew those reporters were going to make money off whatever he said, and DiMaggio wouldn’t get anything in return, save for the hassle of his lost time. Even celebs who need the press—because they have a project to promote, or want to build their name recognition—are usually aware of the pecking order. I fully expect to be kept waiting for half an hour or more every time I have an interview scheduled. Meanwhile, the one time in my career that I’ve missed an interview—because I got the time zones screwed up—the artist refused to reschedule. And of course, some entertainers tend to distrust journalists because when we quote them verbatim and make them look bad, they assume we had an agenda going in. (See the trouble our own Sean O’ Neal had after Chloë Sevigny slammed her own show Big Love; or see what one of my favorite pop-culture historians, Kliph Nesteroff, is going through in the wake of his excellent recent article ...ecky Green, who is so angry about the piece that he’s claimed to be done with i...ws forever.)

Maybe the problem is the disparity between journalists and their subjects. That’s why something like a Prince/Tavis Smiley tête-à-tête seems like such a good idea. If the interviewer and interviewee are on the same level, the subject just might be more relaxed and forthcoming. Or at the least, the audience will get to see the social side of the star, which as noted is a large part of what these interviews are for. But fans have a right to expect at least a little more than low-key chit-chat and unchallenged assertions, yes?

My idea of a good celebrity interview is one like those conducted by Elvis Costello on his Sundance Channel series Spectacle. Costello is a talented musician and songwriter, but he’s also a man of many interests, unafraid to talk to his colleagues about craft and influences. On the recently released second-season DVD set of Spectacle, Costello spends two hours talking to and playing music withBruce Springsteen, and it’s enjoyable to see two of the best rock ’n’ roll songwriters of all time talk about what they heard in each other’s early records: Costello wide-eyed at Springsteen’s vision of a country Costello hadn’t yet visited, and Springsteen pushed by the leanness and toughness of the UK’s punk and new-wave scenes. It’s even more exciting when the two men compare notes on their approach to songwriting, contrasting character songs and pop songs in the context of Springsteen’s classic album The River. Here is a real look behind the curtain.

Of course, it could be that I’m enthralled by the Costello/Springsteen Spectacle interview because these are two of my idols, whom I’ve repeatedly tried and failed to interview over the years. Every time either of them has a new project, I put in a request with the publicist, and every time, I’m politely turned down. If I ever do get the chance to talk to either, I hope I come up with questions that elicit the kind of rich responses they got from each other on Spectacle. And I hope that if either says anything bizarre or controversial, I’ll think to ask a follow-up.

Whatever happens, I know that a half-hour or hourlong conversation will offer just a fragment of who Springsteen or Costello is, which means it’ll never be wholly satisfying. Because ultimately, all the questions we ask and the rhetorical gambits we pull are just variations of: “What’s it like to be you, Mr. Amazing?” And that’s something we aren’t allowed to know, maybe not even if we become amazing ourselves.