From his years at Vanity Fair and to his current role as editor of FourTwoNine, Kevin Sessums is a celebrity chronicler like no other. Trust us.
Kevin Sessums may just be the absolute best person on the planet to take as a companion to an event—any event—be it a fancy Broadway premiere, your sister’s wedding or a seedy afterhours bar. Of this, I’m quite sure. And since I’ve been close friends with Sessums for nearly three decades starting in the me-me-me ’80s that was New York City, the fact that he also happens to be the single best magazine celebrity interviewer this country has ever seen is a fascinating curiosity for me, someone who also happens to swim in that particular pond.
I first met Sessums through a mutual friend (a co-worker of mine at Esquire) when I had just graduated from college and Sessums was the executive editor at Interview, Andy Warhol’s oversized magazine and the unofficial bible of all that was cool in pop culture. We hit it off immediately. We’re both keen social observers (though Sessums is an out-and-out introvert compared to my more gregarious approach), we’re both exceedingly clever with words and puns and, most importantly, we share a biting, merciless sense of humor. No one is spared in our sphere, least of all each other.
I was instantly drawn to the Mississippi native’s (ever-so-slight) Southern lilt his voice revealed but, mostly, I marveled at how self-deprecating someone in his position appeared to be. Media has always reigned in Manhattan and being the top editor at Interview, then later the undisputed king and principal celebrity cover story writer for Tina Brown’s revitalized fame temple, Vanity Fair, made Sessums unstoppable for a very, very long time. He was breathing rarefied Hollywood air. And deservedly so.
To read any of Sessums’ hundreds of celebrity profiles he’s done over the many years I’ve been reading celebrity profiles (his work has appeared in Allure, Playboy, Elle, elevate, Marie Claire and many more), reveals something curious: Sessums is just as important a player in his stories as the famous subject he’s writing about. It’s a ballsy, precocious approach to be sure, but the fact that I buy a magazine expecting to read a long cover story on, say, Julia Roberts, and instead I’m treated to Sessums’ own impressions of how Julia Roberts treated him, is not only unusual, but unprecedented. The reader ends up—impossibly—caring for Sessums (and his opinions) in disproportionate ways. How Roberts or Tom Cruise or Bette Midler or Madonna or Matthew McConaughey or Barbra Streisand or Johnny Depp or any other star treats Sessums is all there for the world to see in his brilliant, conversational, potty-mouth prose. I couldn’t get enough. And I wasn’t alone in that sentiment.
As St. Martin’s Press readies to release Sessums’ expertly written second memoir, I Left It On The Mountain—his first was the best-selling and achingly beautiful childhood tome, Mississippi Sissy—it strikes me as odd that the entire country doesn’t know my friend’s name. It may be too easy to compare Sessums with other literary superstars who happened to be Southern gay men who also happened to chronicle and be surrounded by the most famous people of their day (Truman Capote, Tennessee Williams), but it’s also true. Sessums is a sort of Truman Capote/Tennessee Williams hybrid, a dishy cocktail by anyone’s standards. But in this blink and you’re old news social media bullet train we’re all on, reading a Kevin Sessums story remains the closest I feel to experiencing my buddy curled up on my sofa whispering fantastical bon mots from his latest celebrity encounter.
Kevin Sessums is a storyteller. The best I’ve ever known.
Sessums and I also share the fact that we’ve both magazine editors in chief, two related, but vastly different roles (think of it as the architect and the landscaper of a house; same house, different jobs). Currently, Sessums is the EIC at FourTwoNine magazine in San Francisco, a stunning, pop-meets-culture-meets-words publication that has Sessums’ unmistakable touch on every perfectly executed page. Editing Sessums’ writing—something I’ve had the privilege to do fairly regularly for decades—is both thrilling and fraught with danger. A tightrope I must admit I enjoy more than I should.
I was founding editor in chief of POZ, a groundbreaking magazine about living with HIV that just celebrated its 20th anniversary, and Sessums was tasked with interviewing Ty Goldwater (Ross), the Republican firebrand’s grandson, as Ty revealed for the first time in POZ not only that he was gay, but living with HIV. It was a huge exclusive for a new publication out of the gate and Sessums’ own notoriety would give the story additional gravitas to help propel the fledgling magazine (the accomplished celebrity photographer, Greg Gorman, also agreed to shoot the striking, graphic cover).
When Sessums turned in his first draft of the piece, I read it through and felt nothing—absolutely nothing. It was a competent, by-the-book magazine profile and I was more than confused. Where was the Kevin Sessums I expected? Where was the humor, the ego, the circular prose landing in that sweet spot I expected—no, demanded—from every profile that man writes? So I called him out and he admitted to committing something that is as grave an offense between subject and interviewer as there is in the magazine business: Sessums and Goldwater had sex. Damn.
If I had been the editor in chief at, say, Vanity Fair, I would have absolutely killed the story on the spot—no question about it. If the writer sleeps with the subject, the story is killed. Magazines 101. But since I was the editor at POZ, a magazine specifically targeting people living with HIV, and navigating head-on the powerful realities of sex, suffering, mortality, fear, I implored Sessums to re-write the story revealing everything. I asked him to “leave it all on the page.” The story Kevin Sessums wrote remains one of my proudest achievements in my career and all I did was just let it happen. His tale was nervy, silly, heartbreaking, joyous, sexy and, ultimately, it was the scorching truth. I challenge you to read a better, more revelatory magazine story this or any other year.
POZ was a media sensation from the premiere issue due to no small part to Sessums’ emotionally honest cover story and it got me thinking how different the magazine landscape—particularly when discussing the celebrity feature—has become. Long gone is the era of spending days (or even many hours) with a famous person to get the real story. Today, if you’re able to get the celebrity at all, it’s usually within earshot of a publicist who cuts you off at the mere hint of an interesting question.
But through all of the changes Sessums has experienced in his celebrated career and truly remarkable life—his latest book I Left It On The Mountain—is an absolute must-read—I still think of that first meeting oh so many years ago when I met my slightly older brother from another mother, this Kevin Sessums from Mississippi, and I knew then we’d be friends forever. I was right.
This is worth repeating: Kevin Sessums is the single-best magazine celebrity interviewer this country has ever seen. Not everyone may know that fact, but now you do. Go buy his book and let a master storyteller tell you his story, one of the greatest you’ll ever know.
Kevin, reading so many of your celebrity interviews for decades now, I suspect we have a similar approach to asking the famous questions: We just ask what we want to know. Fair?
To quote Jimmy Carter, “Life isn’t fair.” But this is as fair as it gets, I guess. God, Richard—have we already lost everybody by my quoting Jimmy Carter at the beginning of this interview? [Laughs]
Let’s talk about your career. Tell me about your first paying journalism job? Was it really thrilling?
I feel like you’re interviewing Belle Watling now. [Laughs]
Which celebrities have tried to seduce you (or at least heavily flirted with you) hoping for a positive piece?
I would hope their flirting with me had nothing to do with the story. All interviews are about seductions. The subject is seducing the writer and the writer is allowing himself or herself to be seduced—which is the ultimate seduction. I’ve often said a great interview is like a love affair and a marriage all rolled into one. Then you sit down in front of the computer to write the story and that’s where the divorce occurs—an amicable one. You get to share custody of the story that results.
If you had to sleep with one celebrity, who would it be?
“Had” to? That’s a bit different than “want” to. If I had to? Hmmm. Chris Rock. I’d like to stick a tampon up his ass but without the hot sauce. You’d have to have seen his most recent film Top Five to understand that, I guess. Or maybe I’d tell him it was going to be a tampon and surprise him with my Top Extra Three. [Laughs]
The once proud art of conducting a celebrity interview seems to be gone forever. What was once a week-long assignment living with the celebrity is now 15 minutes with the publicist overseeing every question. Are you glad you started your career experiencing the golden age of the celebrity journalist?
I still have never had a publicist oversee an interview. I go in and ask anything I want. If a publicist has tried to shape a piece beforehand, I’ll listen to the demands and then honor them by going into the interview and telling the celebrity that I have been asked not to ask certain questions but that doesn’t preclude me from writing about the subjects to which those questions pertain. Almost every time the person will tell me to go ahead and ask the questions. But you’re right. We once had a few days to get to know a subject that resulted in a much better piece. To go back to your earlier question—there was more time for that seduction to take place. Now I say that you’re actually lucky to get an hour between a bowel movement and a Botox injection. [Laughs]
Kevin, here’s a question for you. Who’s the best celebrity interviewer working right now?
I’m still working! [Laughs] I think I’m pretty good. I’m humble about a lot of things in my life. Indeed, I’ve been humbled by life as this next book of mine, I Left It On The Mountain, attests. You can’t get any more humble than not being able to take care of your dogs and having to foster them and being homeless and only eating one meal a day because that’s all you can afford because you’ve been stupid enough to become addicted to sticking needles filled with meth in your arm. But I long ago stopped having false modesty about the work I do when I interview people. I’m good at it. Others? I like Alex Witchel a lot when she works in the genre. Jonathan Van Meter. I just read a great story on Laura Hillenbrand in The New York Times Magazine by Wil S. Hylton but he’s more a journalist with varied interest than just writing profiles. In fact, coming back to being humbled as opposed to false modesty. I don’t really consider myself a journalist. I’m a writer who understands narrative and who has a facility for interviewing people because I’m not intimidated by fame whatsoever. But a journalist? I just don’t think of myself as one. I hold that to a higher standard. I hold journalists in higher regard than the job I do. As I’ve told you in the past, Richard, I ultimately consider myself a truck driver. I have a very blue-collar attitude about my day job. I haul glamorous cargo, haul it to deadline, dump it out and get back behind the wheel of that truck.
What was the absolute worst question you ever asked a subject you were profiling?
If I had ever asked them what was the worst thing they had ever asked someone that would have been the worst question. [Laughs] In other words, I have no idea. I tend to block out bad moments. And move on.
What was the absolute best question you ever asked a subject you were profiling?
I tend to block out the good moments, too.
Kevin, here’s another parallel question I know you’re so fond of [Laughs]. Vanity Fair, your home for so many years, was the best place to work because…
They paid their truck drivers well. And your phone calls were returned. And, for a long while, it was a family to me. It was where I found a sense of belonging. But then you finally have to realize your work life is not your family. Your work life is where you do your job. We don’t live in the world of The Mary Tyler Moore Show. But I do tend to miss those people and that life at times. I was just in New York and went up to the offices—it’s the last days there for [Vanity Fair parent company] Condé Nast on Times Square before it moves downtown—and it was rather bittersweet on lots of levels; but really lovely, too. And [Vanity Fair Editor in Chief] Graydon [Carter] was gracious enough to invite me to the Oscar party last year. That sure brought back lots of memories of all the other ones I used to go to when I worked there. It still seemed like a prom filled with all the high school kids who maybe didn’t have a good time at their own proms and were making up for it now as adults. I include myself in that. Hell, I never even went to my prom! [Laughs]
Vanity Fair was the worst place to work because…
I fell out of favor for a variety of reasons. It made me sad. And sadness is a hard place in which to live.
If you could dictate what the next 20 years of your career look like—without regard to money and logic—what would you be doing?
Writing books. And, at the end of each day, handing a few well-written pages to someone I love that would tell me the truth about them.
Tell me the difference between being a magazine editor in chief and a celebrity interviewer.
Change one moment from your life.
Two. When each of my parents died within one year of each other when I was seven and eight years old. That double echo still bounces about in the canyon of my life.
What brings you peace?
Walking my dogs. Waiting for a good sentence and that precise moment it arrives. Nothing beats the arrival of a good sentence. Maybe the arrival of a good man—but I’m still waiting for that. [Laughs]
Who was the one celebrity you always wanted to interview and never did?
If they’re alive, there’s always a chance I will. There’s always hope, Richard. Always. [Laughs]