Calacanis. (Flickr: ElectricSheep)

As TechCrunch first reported,  Inside.com might once again become a functioning web domain, under the administration of Silicon Alley Reporter and Mahalo.com founder Jason Calacanis. And if that sounds to you like a lede from 2000, you probably remember Inside.com as the late-bubble content play—helmed by Kurt Andersen and Michael Hirschorn—that gave us both David Carr and the Segway.

“For 10-plus years I’ve coveted the Inside.com domain name, and I’ve tried to own it,” Mr. Calacanis told The Observer. “I finally got it.”

Although he wouldn’t be specific about his plans for the domain—or what he paid for it—he did note its illustrious pedigree. The address has passed through the hands of Steven Brill and paidContent founder Rafat Ali since the original site went under. When GigaOm acquired paidContent earlier this year, the Inside.com domain came up for grabs.

Mr. Andersen, for his part, can’t believe it’s taken this long for someone to put it to use. “It’s a good name, Inside.com, and I’ve been baffled (but not unhappy) that it’s gone unused for a decade,” he told The Observer. “I find it entertaining and somehow inevitable that Jason Calacanis is acquiring it.”

A few days ago, production company Ish Entertainment quietly posted a "sizzle reel" online. Meanwhile, Ish founder Michael Hirschorn has been squiring Mr. Henry to meetings with agents and network brass in hopes of putting together a deal. 

Mr. Henry has long been prone to overstepping the line, at least when it comes to the standards of morning TV (see, for example, "Moustache Gate"). But he always seemed to get away with it due to a certain lovable impishness. In fact, he won a (Kiwi version of the) People's Choice Award in 2009, then delivered an R-rated acceptance speech that racked up hundreds of thousands of views on YouTube.

Mr. Henry's luck ran out on October 10, 2010, after his mirthful exegesis on the name of Indian minister Sheila Dikshit led to an international incident, accusations of racism and some hasty diplomatic mopping-up by the New Zealand government. It didn't help that NZTV is a state-owned network.

Then again, what better resumé for a career in world's biggest market? (We hear Regis's job is open!)

If anyone can provide Mr. Henry a successful second act, it would seem to Mr. Hirschorn, the Atlantic Monthly columnist and former chief of programming at VH1. "The unacknowledged master" of "the high-low thing," as David Carr put it in a 2007 Observer profile, Mr. Hirschorn gave the world I Love the '80s, The Surreal Life and Rock of Love. And just look what he did with Flava Flav.

In a call with The Observer, Mr. Hirschorn, who's latest effort, a Bravo special based on New York's "Approval Matrix," airs on Wednesday at 11pm, talked up his new discovery. "He's a little bit unique, in the sense that he comes from halfway around the world, and essentially nobody's heard of him before," he said. But CAA has been circling, he added, and reactions from TV executives have been enthusiastic. "It's 'We love this guy. What can we do with him?'" Mr. Hirschorn said, while allowing that "in some cases there's also a certain level of fear." 

About that fear factor: Mr. Hirschorn expressed confidence that Mr. Henry would be able to rein it in when necessary. "He was for ages New Zealand's top presenter," he pointed out, floating a theory that Mr. Henry's implosion may not have been altogether unplanned. "My suspicion is he was eager to get himself fired and probably bored out of his skull," he said.

Mr. Henry's plans are at the moment open-ended. "We're working with him on several fronts—the reality side, the talk-show side and the scripted side," Mr. Hirschorn said, citing The Larry Sanders Show and I'm Alan Partridge as models for a scripted Paul Henry series. 

But the most likely scenario seems to be a talk show of some kind. "Paul intuitively understands what TV is and needs to be in 2011," Mr. Hirschorn said, "i.e., not the Today show circa 1992."

agell [at] observer.com | @aarongell

Provocative though it was, that question was not what had brought Bonnie Fuller, John Stossel, Adam Moss, Nick Denton, Sigourney Weaver, Ira Glass, Judith Regan, Wendy Williams, and a smattering of semi-bold names—some clutching notebooks, many clutching drinks—to this event. They were here at the invitation of The Atlantic, where Mr. Smith is president and James Bennet is editor-in-chief, to enjoy some chili and margaritas and listen to Andrew Sullivan and Michael Hirschorn address the question asked on the invite sent out by the magazine's P.R. team: "What is the Future of Media?"

No answer was supplied during the 30 minute discussion which had Messrs. Sullivan and Hirschorn sitting on a small stage overlooking a rapt—occasionally twittering (and Twittering)—crowd. Mr. Bennet, who moderated the discussion, informed everyone that the two men were once housemates in Washington DC: "The pertinent fact is that I've known Andrew so long, I knew him when he was straight," Mr. Hirschorn joked. (Apparently Mr. Sullivan had "an unreasonably hot girlfriend" at the time.)

Mr. Bennet started the discussion by asking Mr. Hirschorn about that day's New York Times Company quarterly earnings report. "It was pretty dismal," Mr. Bennet, a former Timesman, offered.

"We're in kind of in remarkable, uncharted waters," Mr. Hirschorn said. "There are scenarios in which The Times does not go out of business, but becomes a very different entity."

Mr. Hirschorn, no idle observer, had wondered In the January/February issue of the magazine if The Times could cease printing in May.

The magazine editor-turned-producer foresees "profound changes and they're gonna be unpleasant." Later, he told the crowd of media workers, "I think it might be that there will be a time in the wilderness where there will be a huge and wrenching, horrible fallout... I mean, it sounds like Road Warrior or something. I don't mean to sound like people are eating out of dog food cans. It's really not that bad!"

Apocalypse, soon: Well, that's one plausible future of media.

Mr. Sullivan, pulling on a bottle of beer, wasn't so much concerned with dying newspapers as he was with the promise of blogging, something he'd written about before.

The writer described what attracted him to blogging in the first place: "The thrill was, for me—this was when Clinton was President—you could go on at night and be mean about [a] Maureen Dowd column before anyone had read it... So she would never even get the pleasure of the, like, twenty minutes of praise." This was met with a big laugh from the audience.

Later, Mr. Sullivan told The Observer he posts 300 items a week to his blog, The Daily Dish, calling it "an obsessive compulsion."

The blog, which he started as an independent venture in 2000 according to his bio, was hosted for a period on Time magazine's Web site, before it was brought to TheAtlantic.com in January 2007.

"I'd do it for nothing!," Mr. Sullivan said. "I used to be incentivized for traffic, but we changed that. And I realized, damn, I gave it away."

Working for free: A very plausible future for media as well.

Back in October, executive editor Bill Keller held one of his regular "state of the newsroom" meetings ("Throw Stuff at Bill," they are informally called even by Mr. Keller himself). At this one he addressed a notorious and much-maligned story about John McCain's "friendship" with a certain lobbyist.

“In one case, the famous McCain and the lobbyist story, if I had to do it over again, the one thing I would do differently: I think I would have planned for the blowback better,” he told the staff, according to a recording of the proceedings obtained by The Observer. “It really took a day and a half to decide that we just weren’t going to let the story speak for itself—we were going to speak for ourselves. And by then, they had defined what the story was and, with Fox News as their megaphone, the world now believes it was a story about McCain sleeping with a lobbyist, which it was not. That one I’d wish we did differently.”

Nowadays The Times is showing no such hesitation.

In January, Michael Hirschorn wrote a well-circulated piece in The Atlantic about the Times’ ostensibly crumbling empire. The Times, arguably the most powerful news institution in the country, had been accustomed to unsticking spitballs from its cheek over the course of decades of unflattering feature stories, books, and news items published here and elsewhere. It goes with the territory. Not this time.

Catherine Mathis, the paper’s spokeswoman, shot off a letter to the editor of The Atlantic: "Your article “End Times,” which speculates on whether The New York Times can survive the death of journalism, leaves a lot to be desired from the standpoint of . . .  well, journalism." Yow! She denigrated the piece as "uninformed speculation," and ridiculed what she characterized as the factual errors in the piece.

This week, Mark Bowden wrote a giant, 11,000-word profile of Arthur Sulzberger for Vanity Fair. There wasn't a lot of new stuff here (anyone who has read Tifft and Jones or follows The Times regularly can tell you that). But it certainly was no kinder than Mr. Hirschorn's piece. A chief theme: Arthur Sulzberger Jr. is unqualified to lead the organization into its digital future.

Bill Keller himself wrote a letter to the magazine: aside from the "bombast, the recycled anecdotes and the mistakes an elementary fact-checking" Mr. Bowden hadn't written much of a story. The Times has 1,300 staffers in its newsroom, Mr. Keller pointed out in the letter, not 1,300 reporters, as Mr. Bowden wrote. And he defended Mr. Sulzberger's strategic vision for how The Times can flourish in the digital era: "I'll bet on Arthur Sulzberger finding the answer to that question before Mark Bowden does."

And that wasn't all! Vivian Schiller, former general manager of nytimes.com and the current president of National Public Radio, fired off a letter to the editor of Vanity Fair calling the piece "wildly imbalanced," and concluding the letter thusly: "The business model for Internet news in general is indeed in flux and uncertain, but I am sure that if anyone can figure it out, it is The New York Times of Sulzberger."

Letters like this are new enough for The Times; as we here know, personal correspondence with reporters and editors about these kinds of stories are not rare, but they are rarely written for public consumption. But even publication in the letters section of Vanity Fair, which would not have appeared in the magazine until its July issue because of lead-time, according to a spokesperson for the magazine, was not enough. And so both letters were also sent to Jim Romenesko, the Poynter institute blogger whose links to media news stories constitute the trade home page of the American media industry. Both were published, and both are setting off sparks.

Unflattering features have been written countless times about The Times. But at a moment when every bit of news seems critical to establishing public opinion about the institution—and perhaps more essentially, investors' confidence in the company—The Times is sticking up for itself. That it has to at all is, we think, news fit to print, or at least to publish online.

By the way, according to the Vanity Fair spokesperson, that detail about the number of reporters at The Times will be the subject of a correction in July editions of the magazine; it takes a long time to print and distribute a big volume of glossy paper.

And you won't find one right now on vanityfair.com.

Update 11:20 a.m.: A VF spokesperson clarifies that the story has been changed on the Web, and a proper correction will be forthcoming in the magazine.

The future of the country's leading newspaper—which as recently as early January was called into doubt by The Atlantic's Michael Hirschorn—is touched on in this week's Time magazine cover story by Walter Isaacson, which was updated online after it appeared late last week with following:

Today, The Times' Richard Pérez-Peña wrote Resilient Strategy for Times Despite Toll of a Recession, in which he floated out the "'last-man-standing' strategy," which he quotes New York Times Company President and Chief Executive Janet L. Robinson describing as follows: "As other newspapers cut back on international and national coverage, or cease operations, we believe there will be opportunities for The Times to fill that void." Of course, that's not a plot to survive the recession. Rather, it presupposes The Times definitely surviving the recession, so it's really just an argument for why The Times will still be on top after the dust clears.

Over at Jim Romenesko's Poynter Institute-sponsored media blog, there's a memo written by American Lawyer and Brill's Content founder Steve Brill, which was presented to Times Company representatives including Arthur Sulzberger, Jr. Mr. Romenesko calls the memo "Brill's Secret Plan to Save the New York Times and Journalism Itself, but it also might be called TimesSelect II: The Re-Selecting.

Writes Mr. Brill:

Mr. Brill also suggests readers pay $55 a year for all-they-can read nytimes.com access and proposed the WNYC/PBS pledge-drive-ready slogan "An Old-fashioned Tradition is Back: Read the Times for 15 Cents a Day." (Sounds like Bill Murray's old "Listener Supported Radio" skit from National Lampoon's That's Not Funny, That's Sick! to us.)

Observer alum Gabriel Sherman weighs in with a piece on The Big Money called Micro Economics with the subheadline "Why Steve Jobs and micropayments won't save the media." Writes Mr. Sherman:

Meanwhile, in New York magazine, Will Leitch looks at Twitter and finds The Times news-gathering hegemony being pecked at by the ubiquitous blurt-blog platform that some evangelists think can replace traditional journalism (while, Mr. Leitch points out, also failing to make any money):

Beating The Times by 15 minutes! (The Times' Lede blog took notice of this, too.) Of course, The Times had all sorts of relevant details, like the fact that U.S. Airways flight 1549 didn't so much crash as land safely with all passengers escaping mostly unharmed (probably something family members of passengers might want to know), but, man, it took The Times 15 whole minutes to get on the story.

So, does that mean manolantern will be "the last man standing"? Glp.

Mr. Hirschorn looks at the Times Company's difficult year—and its possibly even more difficult year ahead—before concluding that:

What would that mean for readers? Mr. Hirschorn writes:

Twelve year-old Third Eye Blind references aside, Mr. Hirschorn sees a future digital-only edition of the paper that looks a lot like The Huffington Post, which he describes as "the prototype for the future of journalism: a healthy dose of aggregation, a wide range of contributors, and a growing offering of original reporting." (We assume however, that this hypothetical future Times would pay its contributors, unlike the current, actual Huffington Post.)

Under this digital-only scenario, Mr. Hirschorn speculates that 80 percent of the paper's staff might be laid off, but he also predicts that some Timesmen and -women like Thomas Friedman, Paul Krugman, and Andrew Ross Sorkin might "succeed as independent operators," which might prove "more profitable than fighting as part of a union for an extra percentage-point raise in their next contract."

Will it happen? We'll tell you in May. 

During the show, master capitalist 50 subjects his poor droogs to “inventive challenges that 50 Cent helped to create, while mastering the skills that took the rapper from his hard-knock life to the top of corporate America.” (So what, they have to drink Vitamin Water?) “Each week,” the press release continues. “50 Cent will narrow down his search by testing the candidates on the knowledge he has taught them while pushing them to their limit.” The winner—i.e. the lucky soul who maintains the “strongest combination of business flair, strength, ambition, and fearlessness”—will win $100,000, thus “pav[ing] the way to future mogul status.”

Of course, all this rigmarole is simply a ten-hour commercial for Fiddy’s latest entrepreneurial endeavor, The 50th Law—co-authored by Robert Greene (The 48 Laws of Power)—in which Mr. Cent “share(s) the lessons he learned as a street hustler and how those lessons allowed him to become the massive success he is today.” Apparently, 50 Cent does actually have some music in the pipeline. The eerily prescient, Before I Self-Destruct hit stores on December 9.     

The company will be based in New York and Los Angeles and will focus primarily on non-scripted television.

The broader diaspora of MTV, VH1, CMT, and Logo has formed an exclusive first-look deal with Ish Entertainment for three series, which, according to the announcement, "will provide Ish with development funding and overhead with the aim of bringing Hirschorn's successful development and production talents not only to VH1 but to the entire Music and Logo Group."

More from the announcement:

Mr. Hirschorn had a hunch that while baby boomers liked their nostalgia straight up, younger audiences preferred to revisit their cultural pasts under the cover of irony and humor. Getting wise-cracking comedians and actors to make fun of the movies, TV shows and music videos of their youth, he figured, could be a way to allow viewers to reengage with those long-forgotten products, and revel in a shared cultural heritage.

He snapped up the concept on the cheap, and quickly cranked out a pilot. Thus was born I Love the ’80s, which debuted in December 2002—and went on to become the new VH1’s signature hit. The premiers of the first 10 episodes averaged one million viewers, a 175 percent improvement on the time slot’s average at the time, according to VH1. The show also poured the foundation for the channel’s emerging sensibility—sassy, retro and unapologetically pop-obsessed.

Mr. Hirschorn was sitting across from NYTV at an haute–taco restaurant on 50th Street as he told this story on a recent afternoon. It was drizzling outside, and Mr. Hirschorn, who had neglected to bring an umbrella, was glistening. He ran his hand through his wet brown hair and went on explaining how, in the years since that initial triumph, he has used that same highbrow editorial sensibility to help pioneer for VH1 a new genre of lowbrow reality programming.

Mr. Hirschorn’s key insight was, in a sense, conceptual. The first wave of reality TV tended to create drama by putting broadly recognizable people into contrived contests—surviving on an island, or competing for the heart of a handsome suitor, for instance. VH1 shows, by contrast—along with the plethora of imitators they’ve spawned—are more likely to play on viewers’ fascination with both the glamour and depravity of stardom. The channel has had hits with shows like The Surreal Life, in which wizened and bloated celebrities, “forced” to share a house in the Hollywood Hills, gleefully back-stab for the camera; Rock of Love, in which 20 lusty ladies vie for the heart of former Poison frontman Bret Michaels; and Celebrity Fit Club, in which portly former stars compete to drop pounds and revive their sagging careers.

Mr. Hirschorn declined to say how much he makes, but according to a source, he earns over $1 million in total compensation. Still, by all accounts, he’s earned every penny. “His ability to tap the B-list nation for fresh material is breathtaking,” said New York Times media columnist David Carr, who once worked for Mr. Hirschorn at the short-lived journalism Web site Inside.com. “He did not invent the high-low thing, but I think he is the unacknowledged master of it.”

That’s an unlikely identity for Mr. Hirschorn, who once looked destined to make an impact in a more literary sphere. Until joining VH1 six years ago, he had spent most of his career as a writer and editor of high-end magazine journalism, and he still writes a regular column on culture for The Atlantic Monthly. So how did Mr. Hirschorn—who earned a master’s degree in comparative literature from Columbia University, producing a thesis that analyzed a linguistic riddle in Nabokov’s Pale Fire—get from studying the language of Vladimir Nabokov to subtitling the language of Flavor Flav?

“I haven’t resolved that conflict—if I’d like to be a populist, or highbrow,” said Mr. Hirschorn over lunch, by way of explanation. “That’s why I do both.”

To better understand the source of those competing impulses, it helps to go back a ways. Mr. Hirschorn grew up on East 51st Street in Manhattan. His mother was a journalist who wrote for The Economist and edited the op-ed page for the Journal of Commerce. His father owned a business specializing in noise control engineering.

“We were a European immigrant, super-highbrow family, collecting autographs from Vladimir Horowitz,” he went on. “I went to piano recitals at Carnegie Hall. We bought a TV to watch the moon launch. I was only allowed to watch Masterpiece Theatre and Jacques Cousteau.”

Pop culture was the forbidden fruit. Decades after the fact, Mr. Hirschorn still gets excited recalling his pilgrimage to see the members of the Beastie Boys, when they were in The Young and the Useless in the early 80’s. “Hip-hop, when I was a teenager, was a way of being cool.” (When asked what he felt most proud of at VH1, Mr. Hirschorn named, among other shows, Ego Trip’s The (White) Rapper Show—a reality series, in which 12 aspiring Caucasian rappers, lived in a tenement in the South Bronx and competed for street cred, airtime and $100,000.)

After grade school and high school at Collegiate on the Upper West Side, Mr. Hirschorn went to Harvard, where he threw himself into the Crimson. But his senior year, he was beaten out for president of the paper by Jeff Zucker, who now runs NBC Universal. (Years later, Mr. Hirschorn would get his revenge, slamming his old rival in a piece in Esquire.)

Then, while doing his masters at Columbia, Mr. Hirschorn began writing freelance magazine articles, on culture and business. “The people who were in academia were like, oh, my God, you wrote for The New Republic,” recalled Mr. Hirschorn. “So you must have had a hundred readers rather than one.”

Mr. Hirschorn enjoyed playing to a broader audience. Soon, he had thrown himself into the world of glossy magazines. As it turned out, the son of a noise reducer had a knack for making noise. Over the next decade, he climbed fast, serving as features editor at Esquire—where a regular column he wrote, called “Trash Culture,” offered a hint as to where his interests were heading—then as executive editor at New York, and as editor in chief of Spin.

In 1999, Mr. Hirschorn teamed up with Kurt Andersen, the co-founder of Spy, to launch Inside.com—which they billed as a “must read online site for members of the cultural elite.” Though the site generated buzz among that elite, it never became profitable. The site’s failure, said Mr. Hirschorn, “was incredibly painful.”

Still, he kept looking for the next big thing. In the summer of 2001, Mr. Hirschorn parlayed his reputation as a know-it-all music geek into a gig at VH1. At 37, it was his first job in television. “I had watched maybe 10 minutes of VH1 before that,” he said. “But it was a lot more money than I had been earning.”

At first, Mr. Hirschorn struggled. The idea was that he would produce news segments about the music business. But he knew nothing about television development, and his ideas went nowhere. In the summer of 2002, Viacom brought in MTV wunderkind Brian Graden to shake up the stagnant channel. Mr. Hirschorn prepared to be fired.

Instead, Mr. Graden coached him on the basics of TV development and sent him searching for aberrant material. Anything that would attract eyeballs. “That first year was essentially pure, creative chaos,” recalled Mr. Hirschorn. “It was the wallpaper strategy. We’ll slap everything up there and figure it out.”

That was how he stumbled upon the idea for I Love the ’80s. Meanwhile, Mr. Graden had scooped up The Surreal Life, which had been running on the WB. During the third season, which aired on VH1 in 2004, former Public Enemy rapper Flavor Flav struck up a disaster of a romance with Danish D-List actress—and former Mrs. Sly Stallone—Brigitte Nielsen. Mr. Hirschorn and his colleagues knew a mesmerizing train wreck when they saw one. They green-lighted a spinoff series called Strange Love chronicling the unlikely affair.

There was more, of course. When Flavor Flav and Ms. Nielsen broke up, Mr. Hirschorn went with another spinoff from the prolific producer Mark Cronin, called Flavor of Love, in which a cast of ragtag women competed for Flavor Flav’s affection. Last October, the 90-minute season finale of Flavor of Love 2 attracted 7.5 million total viewers, a VH1 record, and among black adults 18 to 49 earned an 18 rating and a whopping 34 share.

And on Oct. 15, VH1’s new block of Monday night programming attracted more 18-to-49-year-old viewers than any nonsports-related programming that night. The Salt-N-Pepa Show, which chronicles the comeback of the eponymous 80’s female rap group, drew 2.2 million total viewers and a 1.3 rating in the 18-to-49 demo.

VH1 has ridden its unapologetic embrace of the lowbrow to become one of the most recognizable brands in a crowded cable universe, and has enjoyed 21 straight quarters of ratings growth. According to estimates from industry analysts at SNL Kagan, VH1’s year-end advertizing subscriptions jumped this year from 74.2 to 93.7 million, and ad revenue was also way up.

And so, with his success in television more or less secured, Mr. Hirschorn is left to grapple with the same internal quandary that has bedeviled others who have made a similar transition from highbrow aesthete to purveyor of mass-market pleasures.

Call it the Frederic Thompson Syndrome.

To wit: In 1904, a frustrated design student named Frederic Thompson dropped out of architecture school, moved to New York, and became the first architect to work wonders on Coney Island. As chronicled in Rem Koolhaas’ Delirious New York, Mr. Thompson used a patch of the island, called Luna Park, to pioneer a freakish form of what might be called extreme architecture, which ranged freely over various styles and traditions, and included over a thousand “towers, minarets, and domes.” The crowds loved it.

Thompson’s creation was disdained by highbrow critics, including the Russian playwright Maxim Gorky. In response, Thompson articulated an elaborate manifesto defending his work—a defense, in retrospect, perhaps designed as much to assuage his own internal doubts as those of his external critics.

This May, Mr. Hirschorn used his Atlantic column to pen a similar manifesto. Under the heading “The Case for Reality TV: What the Snobs Don’t Understand,” he argued that the format allows for “the best elements of scripted TV and documentaries while eschewing the problems of each.”

Over lunch with NYTV, Mr. Hirschorn continued his campaign. Reality shows, he said, often dare to touch “third rail” issues, such as race and class, which conventional dramas and comedies tend to avoid. “A lot of scripted television now gets no ‘Updike points,’” he said.

His ability to toss off phrases like “Updike points” suggests that Mr. Hirschorn still aims to keep one foot—at least mentally—on the high ground. There’s the Atlantic column, for one thing. And he has kept up ties with his old New York journalism friends: At his apartment in Chelsea, where he lives with his wife--a book editor at St. Martin’s--and two children, Mr. Hirschorn hosts a poker game for media types. CBS’s Gil Schwartz, The New Yorker’s Tad Friend, New York Magazine’s Adam Platt, Slate’s Jacob Weisberg and HarperCollins’ David Hirshey have all played.

So have any of Mr. Hirschorn’s friends in polite society ever needled him for being a prime mover behind, say, America’s Most Smartest Model—in which, according to VH1’s Web site, 14 “‘himbos’ and ‘bimbos’ face challenges that put both their overall intelligence and their beauty to the test”? According to Mr. Hirschorn: no. Perhaps, NYTV suggested, the Atlantic piece was Mr. Hirschorn’s defense not against the external Gorkies of this world, but rather against the part of his brain that used to dabble in Nabokov?

“I think I’m constantly self-doubting and self-interrogating on everything,” said Mr. Hirschorn. “I think that it’s a slightly shtetl mind-set, if you’re always trying to figure out what’s wrong with what you’re doing and the vulnerabilities of it, nobody will figure it out before you do.”

But for all that anxiety, he’s having a blast. “I get to hang out with hilarious people and freaks and all sorts of bizarre, wonderful characters,” he said.

And friends confirm that he’s far from tortured. Mr. Andersen, his former mentor and business partner, said that he has never seen Mr. Hirschorn happier than in recent years. “I think he got over worrying about somehow being true to his master’s in comp lit and his Harvard degree,” said Mr. Andersen. “When you’re good at something, it makes you happy. He was never the kind of pointy-headed intellectual sort who looked down on entertaining crap.”

“It’s not like he decided, I don’t care about Nabokov anymore, it’s Flavor Flav for me,” Mr. Andersen went on. “He’s a man of many parts. Wallace Stevens sold insurance while he was writing great American poetry. There are histories of people doing these improbable things in different parts of their lives.”

Back at the upscale taco joint, Mr. Hirschorn ordered a cup of coffee. He said that one of the greatest influences in his life was a book by John Seabrook, called Nobrow: The Culture of Marketing, the Marketing of Culture.

“You can look at opera, which was the ultimate lowbrow activity of the 19th century,” he said. “And now you have to wear a fur to go see it. So I think these things are completely arbitrary.”

Some day, he said, he’d like to write a book or make a movie. Where might those projects fall, on the Flavor-Flav-to-Comp-Lit scale?. “Again, it’s sort of the no-brow thing,” said Mr. Hirschorn. “For me, all creative ideas sort of exist on one plane.”