From The Archives: The Freelantzovitz Files

A ‘Vanity Fair’ column lampooning late-nineties freelance life (A.K.A. the glory days)

Image: Luke Chesser via Unsplash

It’s not the best time to be a writer: amid the “consolidation” of Condé Nast and Hearst, the mass layoffs at MTV News, and the New York Times and the great “pivot to video.” I could envision a column devoted to the lifestyle — a kind of “Sex and the City” but for freelancers trying to scrape together a living out of 1099s. A few months ago, paging through old issues of Vanity Fair from 1997, I found an occasional column in the “Vanities” section that wasn’t too far off, called “The Freelantzovitz Files.” It was the tongue-in-cheek diary of Josh, a Park-Slope-dwelling aspiring writer who annoys, pesters and stalks editors, collects rejection slips and restraining orders.

Twenty years ago, things were a lot different: after paying your dues as someone’s assistant, you were bound to experience (more or less) smooth sailing in your career. Freelantzovitz, however, seems to have completely missed that boat, and instead embarks on a series of clumsy misadventures. In 2017, they felt as timeless as a Greek tragedy, at least to me — I was collecting my fair share of boiler-plate rejections when I was not straight-up ignored.

from ‘Vanity Fair,’ November 1996

Josh Freelantzovitz’s lampoon diary was conceived by David Kamp who, as a young editor at GQ in the early-to-mid 1990s, was still learning the tools of the trade. Beside the queries from polite freelancers, Kamp dealt with a series of aspiring writers who “hadn’t read the magazines, who were pitching rather relentlessly, aggressively and rudely.” To overcome the boiling sense of frustration, he came up with a comic doodle outlining the weekly diary of one of those wannabe writers. He passed it to Graydon Carter as an inside joke. “It wasn’t meant for publication, it was just ‘familiar with this guy?’” Kamp recalled. “[Carter] just said “this is funny, let’s print it.” It ended up running from 1996 to 1999 (my index-based research, coupled with a Condé Nast librarian’s assistance, only yielded seven entries). Illustrator Tim Sheaffer gave him the look of a young Michael Chabon, minus his charm.

The diary, which detailed the weekly deeds of Freelantzovitz, usually contained an inane idea (e.g., a magazine called @water, a partnership request to Rupert Murdoch) followed by pitches (email Joe Dolce!!) usually facilitated by Josh’s friends, a rejection slip or an underwhelming assignment.

from ‘Vanity Fair,’ May 1999

A feeble attempt at immersion journalism (sniffing heroin, stalking Lou Reed) would follow. The week usually ends in an underwhelming manner, with Josh getting food poisoning or reeling from the umpteenth rejection, which was usually the case after sending an editor he admired, say, a bag of prized coffee beans.

His sentences are pompous but with an underlying puppy-like enthusiasm, and his schemes to become famous or finally meet the executives of his dreams are as intricate and as childish as Wile E. Coyote’s ploys to tame the Road Runner. At one point, he planned a lawsuit against Woody Allen — “Clearly, he based the Kenneth Branagh character in Celebrity on me,” he wrote, “Leo must have told him about my abbreviated tenure in his posse.” The accompanying illustration featured him sleeping next to a defaced poster of Woody Allen.

from ‘Vanity Fair,’ December 1997

Other writers, who were contemporaries of Kamp-as-Freelantzovitz had strong feelings towards the character. “Josh was the embodiment of naked, stupid ambition: All grasping and no talent,” said writer Matt Haber, who once equated Freelantovitz with Jacques Hyzagi (remember Elle on Earth?) with Freelantzovitz. “As a wannabe writer myself at the time, I was also a little insulted by Josh and his grabby, grubby machinations: His schemes to get into print were so much better than mine!”

Virginia Heffernan, in a 2010 review of the iPad version of Vanity Fair for the New York Times, recalled the adventures of Freelantzovitz as “horrific,” and “too close to home.” Heffernan used to read, cringe and laugh at the adventures of Josh Freelantzovitz with her then roommate and fellow writer Mike Albo. “In every letter (!) I wrote to the Village Voice or The New York Press I did feel like one of those 19th-century characters in maybe Balzac who has come to the city with his sheaf of poems and letter of introduction from a friend of his uncle’s,” she wrote in an e-mail. “The letters I wrote were so humble and even craven — I had of course studied every article in the Voice for 10 years and was prepared to praise every one of them as groundbreaking — and it was fun to see this as a citywide practice, even as I knew it wasn’t, beyond the small world of English majors dreaming of making $25,000/year at the Voice.”

For his art, Albo said he still thinks about how Josh Freelantzovitz was “as pathetic and desperate” as he was. “There must be something perennial about him, because I still scramble like he did, even in the age of our Freelance Isnt Free Act,” he wrote “Just two days ago in fact, I had to send one of those ‘My payment for TKTKKT is 90 days past due of the 90 day window you said you would pay. If I dont receive this payment by Friday I will contact my lawyer.’ And not only did I write that, but I had to have my LIFECOACH handhold me into composing and sending it IRL! No joke! I AM JF!!!”

Former Vanity Fair contributing editor Toby Young, in his memoir How to Lose Friends and Alienate People, recalls how he reacted to one Freelantzovitz sample with sanctimoniousness: “It was unseemly, I argued, to poke fun at people who were struggling to obtain the professional status that Vanity Fair’s contributors had achieved. […]The author of this piece, I said, holding up the offending article, is a snob, wanting to kick away the ladder that he himself has climbed so no one else can follow.”

Josh Freelantzovitz’s cover letters contained grandiose statements such as “I hold the key to the future” and “I am a visionary, I am uniquely qualified”; his pitches always came three to six months too late, meaning his topics of interest (heroin-chic, young people smoking cigars while listening to lounge music) had already been covered, and his unpublished fictional material consisted of cringeworthy titles such as The Gatsby of Wesleyan and Kolumbia Kounty, a potential indie-road-movie about a “handsome, but moody freelance writer” who goes on a crime spree in the Hudson Valley after his parents cut him off. The only writing assignments he managed to snag in the New York Post and Time Out New York were round ups on “The Best Kissing Spots in Murray Hill” and a listicle of the “Best Internet Cafes”.

Even though it was painfully clear that I was dealing with a piece of satire, I have to confess that my first thought, upon reading those old columns, was, “Haven’t we all, to some extent, been there, writing cover letters full of self-aggrandizing statements, being met with silence or polite passes from potential editors, having to resort to writing listings and round-ups?” Well, we have, but, I would learn from Kamp, the problem here is the attitude.

When I contacted Kamp to know more about the character, he told me that my reaching out to him was one of the most eccentric requests he ever got, and that Freelantzovitz, for him, was nowhere near the stereotypical rookie writer. “I was surprised because I never meant for him to be someone who was identifiable to the reader,” he said “He was meant to be a nuisance, an irritant, He wasn’t supposed to be the character you read about and go ‘oh, that’s me.’”

Three days of Josh Freelantzovitz’s life, from ‘Vanity Fair,’ October 1996

The lack of talent and dubious work ethic weren’t Freelantzovitz’s main tragic flaws, though. Entitlement was his crux. “He had the sense that the world owed him literary success, whether or not he had the talent for it,” Kamp explained. “He was meant to represent a particularly irritating breed of entitled writer, which still exists to this day. People who aren’t necessarily that good. They might be very driven, but they’re not that good.”

To Freelantzovitz’s meager defense, the magazine industry in the 1990s, without online outlets or editors that offer their contact information in their Twitter bio, was a much tougher battleground ground than it is today: it was harder to get your name into print, there were fewer outlets, there was not much internet to speak of, and email was not commonplace until the late 1990s, Kamp told me. Pitching consisted of sending query letters and then you would follow up by cold-calling the office: “The website offers more opportunities,” executive editor of GQ Devin Gordon told me, commenting on the limited real estate of his print publication. “But with each year, as the site grows, our expectations for the quality there are higher and higher as well.”

That the bar was so high was beyond Freelantzovitz, though: along with his brother Joel, who sporadically got his column too, “The Fabulous Freelantzovitz Boys,” detailing the toils of an aspiring Hollywood screenwriter who also had to remotely babysit his Brooklyn-based sibling, he was raised to believe he was a star. At one point, he pitches Norm Pearlstine — then at Time Warner — the idea of a new magazine named JOSH, a title that, allegedly, would “leave GQ, Esquire, Details and Men’s Journal in the dust,” thanks to a never-before-seen sex column he thought he had the authority to write based on an accepted condom review for Details (never published) and a quiz for Maxim (same).

“When I first came to New York, I met people who would be 22–24 years old and they were [all like] ‘the world is awaiting my talent,’” Kamp recalled. “It still amazes me that people come up that way. My idea was that Josh and Joel were those two guys who thought, ‘the world is waiting.’”

At some point, Josh Freelantzovitz specifically thought that the world was waiting for him to be the next James Wolcott. When launched, Wolcott had a blog hosted on the site, and Kamp resurrected the character and made him some kind of stalker: without an inch of Wolcott’s talent, the best Freelantzovitz could do was troll him, posing as a media insider who could afford to be dismissive of Wolcott’s work. “Graphix cool, but Wolcott blog jejeune [sic] and pedantic;” he wrote in the Forums (unfortunately no longer available, but thanks Baltimore’s Finest Trash for copying these comments.) “I’d do it much better if only they’d let me. Still, a site to keep an eye on, my friends”

Despite Freelantzovitz’s awful personality and incompetence, though, Kamp decided to give him a relatively bright future. First he had him relocate to Flushing because he got cut off by his wealthy parents based in Brookline, MA. Kamp saw the move as a hopeful sign of resourcefulness in his character; a couple of years later, Josh and Joel Freelantzovitz co-founded Brookline Boys, a company that manages the production company “Sack O’Coaster”, and, here and there, they sold pilots to the likes of HBO. “Experience has taught me that certain people succeed due to relentlessness rather than kindness or talent, and people like that tend to find some niche,” Kamp said. “That type of person does eventually find some foothold somewhere. Through pure relentlessness, they’re failing upwards”.

What if he had persisted with his journalistic ambitions, though? I would picture him as a staff writer for one of those content mills: there, he would try to elevate his aggregated-news posts with some obscure, or pathetic, cultural references in the attempt to sound smart, in the hope that he would be offered to publish an essay in, say, an n+1 anthology. His 23-year-old boss would rein in his flights of fancy. Haber had an even better idea: he’d be an enthusiastic retweeter, an inveterate link-sharer, a new platform early adopter, and an obsessive Facebook friender “He’d tweet things like If I still did stuff for @nymag I could write 4k words on #covfefe,” Haber speculated. It makes complete sense.