On the first Friday in May, a line of advertising and media people stretched down New York’s West 22nd Street, waiting to hear from Shane Smith, the 45-year-old bearded and bearish co-founder of Vice. One of the media world’s most flamboyant CEOs had an announcement to make.

The occasion was the Digital Content NewFronts, a corporate event where media companies parade upcoming digital programming before advertisers. While some CEOs came in button-downs and blazers, Smith wore a black T-shirt, a tattoo peeking out from under his sleeve.

In a rollicking, obscenity-laced presentation featuring Oscar-nominated filmmaker and Vice creative director Spike Jonze, Smith unveiled a host of new lifestyle shows starring a who’s who of tastemakers for millennials. Marc Maron, the sardonic comedian who runs a popular podcast of celebrity one-on-ones, will have an interview show; Ellen Page, the actress from Inception and Juno who came out as gay last year, will host an LGBT travel show, “Gaycation.”

But unlike the bulk of Vice’s news and cultural programming, which runs online, the shows are expected to air on Vice’s new cable channel on A&E Networks, which paid a cool $250 million for a 10 percent stake in Vice last year. At the media industry’s premier digital advertising event, Vice’s big news sounded almost anachronistic: the plucky internet video mavericks were moving to cable.

Vice News covers the fight against Boko Haram in Nigeria.

Shane Smith interviews Justin Trudeau of Canada’s Liberal Party.

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It’s not just their culture shows moving to TV. Vice is also increasingly throwing its weight behind hard news, and in late March, the company announced a deal with HBO that will expand its vaunted documentary series and give Vice a 30-minute newscast every weekday.

Vice rakes in money from the deals, and the prestige of making its mark on a traditional medium. A&E and HBO get to raise their profiles among Vice’s coveted millennial audience. Besides, it’s not the worst time to make a play for nightly news. NBC’s once-trusted heavy hitter, Brian Williams, was recently suspended, Al Jazeera America’s newsroom appears to be in tumult, and CNN seems to rack up on-air faux pas by the week.

Their fall coincides with Vice’s rise. Smith has long said he wants Vice to be “the next MTV, ESPN, and CNN rolled into one,” and in 2015, that has started to become a reality. Vice is no longer the edgy digital outsider, but a slick global empire lubricated with millions in investment and ad dollars that, coupled with a brash attitude, make the company a ray of light among the decaying temples of legacy journalism.

Vice’s attraction for its valuable millennial audience is predicated on the notion that it is real and raw, not plastic and prepackaged like the rest of the mainstream media world. But it may be truer to say that Vice simply packages itself more deftly than almost any other big media company.

I don’t think that being silly, being stupid, is cool anymore. When you look at the planet, at the state it’s in, it demands a certain level of seriousness.

“Vice has been very smart and strategic in how they position themselves and how they are reflected in the media,” said Eunice Shin, director of Manatt Digital Media, a consulting services and venture capital firm for media businesses. “And that’s all purposeful.”

Vice has mastered the mass production of authenticity for profit. But editorial standards change when your aim is not to be an entertainment company, but a trusted source of news.

Vice believes it is up to the challenge. Alex Miller, Vice’s global head of content, says the company has grown up. “With expansion comes a sense of responsibility,” he told me recently in one of Vice’s glass-walled conference rooms. “As time goes on I don’t think that being silly, being stupid, is cool anymore. When you look at the planet, at the state that it’s in, it demands attention. It demands scrutiny. And it demands a certain level of seriousness.”

Does the oft-repeated Vice maxim to do “smart in a stupid way and stupid in a smart way” still apply? “I think we just do everything in a smart way, hopefully,” Miller said.

VICE’S HEADQUARTERS are a 30,000-square-foot amalgamation of converted warehouses in Williamsburg, Brooklyn—hipster capital of the US. Smith, who was not made available for an interview with CJR despite repeated requests, has called his office of 425 workers “a sweatshop for trustafarians” and the culture “like an incestuous family.”

The interior matches Vice’s style: gritty yet polished. There’s the meeting room with a stuffed bear, a memento from a video shoot. When I visited in April, the famed office bar was temporarily gone in anticipation of Vice’s upcoming move to a space double the size.

Rings with the Vice logo are worn around the office. New employees sign a non-traditional workplace agreement, acknowledging that, among other things, “sexually provocative and other explicit images, videos and audio recordings are regularly present in VICE’s offices.” And the company throws events like a charity ping pong match in March between senior editor Benjamin Shapiro and Rolling Stone’s Gus Wenner, and last December’s 20th anniversary party, where rapper Lil’ Wayne performed. The event was preceded by Smith personally handing out envelopes of $1,500 in cash to employees at the staff holiday party.

For young journalists, joining Vice seems to mean living a sensuous life and doing important work. While most new media gigs connote aggregation drudgery and hot takes, Vice staffers—average age 26 to 27—make longform documentaries, roam the globe, and largely eschew the clickbait content farm. As old media struggles to adapt to digital technology, Vice throws itself into experiments with Google Glass, debuts virtual reality news at Sundance, and launches new products such as Broadly, a soon-to-arrive vertical for women and a first for a brand built on laddish insouciance. Smith has made journalists optimistic, a rare feat in today’s gloomy media world. “As a young person, you have the chance to rise a bit higher and do things you can’t do waiting in line at a place with older, more experienced journalists,” a former employee told me.

A scene from Vice’s award-winning documentary “The Islamic State”

Monica Villamizar reports from the protests in Baltimore this April.

With $6.5 million in state tax incentives for creating 525 jobs in Williamsburg, the Vice machine is expanding, too. Vice has described its salaries as “competitive with comparable emerging media companies,” but many employees seem to be here for the work and the culture, not the money.

“There’s a sense that you’re lucky to be there,” said one former employee. “What you don’t get paid for in cash is made up in the cool factor, and maybe getting into their parties.”

“It’s like a cult,” said another ex-employee.

Vice may not quite have the biggest audience in the media world (comScore data shows 32.4 million US unique visitors in May, compared to BuzzFeed’s 74.7 million, though this excludes Vice’s reach on YouTube, TV, and social channels), but it certainly has the most hype, and a lot of money. The privately-held company is worth at least $4 billion, Smith told The New York Times. The paper also reported, based on an internal document, that Vice expects to make $915 million in revenue in 2015.

Old media is taking notice. “We want to learn from them,” said Nancy Dubuc, A&E Networks’ president and CEO, earlier this year at New York’s Paley Center for Media. “They’re talking to a generation that we’re struggling to connect to.”

The image Vice projects is of a mature, openly corporate organization that still has the swagger of its youth. The challenge, as its workforce of 1,500 employees in 36 global offices expands, is how to distance itself from its crude past, yet hold onto enough of that reputation to cement, and grow, its authority with its core audience.

It’s a puzzle that preoccupies company managers. Ellis Jones, Vice magazine’s first female editor-in-chief, said she has been tasked with “trying to figure out ways to appeal to a larger audience who might see us as what we were 10 or 15 years ago.” The magazine remained Vice’s final bastion of tastelessness even as the company has moved into current affairs—“Last Words,” a fashion spread depicting female writers killing themselves in 2013, was later retracted—but two recent issues were dedicated to fiction writing and climate change.

Vice is in an awkward position: It may bear little resemblance to its identity for most of its history, yet also has an interest in showing that it hasn’t really changed that much.

TO UNDERSTAND the cultural shift underway at Vice, imagine that MTV’s Jackass, instead of fading into obscurity, now produces exclusive documentaries about ISIS from Syria and Iraq. Vice.com is still disproportionately preoccupied with sex workers—case in point: “Twenty Hours in a New York Strip Club”—but the crudest material has gradually been defanged.

Vice arrived at its current incarnation by a circuitous route. It emerged in 1994 as the Voice of Montreal, a countercultural magazine funded by Canadian welfare money that was brazen in generating hype. It published stories like “Gays or Girls?” in which two blindfolded men received oral sex from a man and woman and had to guess which was which, or the recurring “Gross Jar” feature, in which ingredients like facial scabs and a dead baby pigeon were mixed together, left for weeks, and documented. When the magazine was accused of lacking diversity, co-founder Gavin McInnes—who split from Smith and Suroosh Alvi in 2008 over “creative differences”—told Canadian media critic Jesse Brown that he wrote under black or female pseudonyms. It was caustic, unapologetically offensive and, to its audience, cool.

In 2006, Vice launched The Vice Guide to Travel and turned its attention towards online video. The company received an injection of private equity in 2009, then began to professionalize. Former Viacom chief Tom Freston became an advisor, and Vice got famed Hollywood talent agent Ari Emanuel to represent the company. CNN’s Fareed Zakaria and talk show host Bill Maher joined as producers on the HBO documentary series, along with BJ Levin, best known for producing reality TV shows like Project Runway, which put Vice on the cultural map.

I wouldn’t say news is the ugly duckling sibling, but there’s a definite difference between news and the rest of the building.

Today, most of Vice’s content lives online under 10 websites, or “verticals,” encompassing everything from Fightland, about mixed martial arts, to Thump, on electronic dance music. While Vice started life as a hip magazine, it is now at heart a video operation, and its best content, across all its verticals, are mini-documentaries that are also hosted on YouTube. Its flagship, however, is not a website, but Vice’s half hour-long HBO documentary series, originally conceived as “60 Minutes meets Jackass.”

Vice News, another vertical that launched last March, has scooped up Webbys, Peabodys, and a National Magazine Award, while scoring interviews with President Barack Obama, Vice-President Joe Biden, and James Mitchell, the so-called “architect” of the CIA’s interrogation program. With the HBO newscast, hard news will soon consume even more of the company’s resources.

But as Vice has increased its output of serious journalism, there have been growing pains. The wall between editorial and advertising, where Vice gets much of its revenue, can be porous. Last year, Charles Davis, a Vice associate editor who was let go after two months, posted an email from a Vice editor on Twitter saying that every story involving a large brand had to be “run up the flagpole” to general manager Hosi Simon, even if the brand didn’t have an advertising relationship with Vice. He received the email after approving a freelancer’s story that called for a boycott of the NFL. While the editor who authored the email wrote that in his experience, Simon “simply says ‘ok’ to almost anything,” Davis tweeted that “In my experience, every single time—every single time—I had a story ‘run up the flagpole’ it was killed.” Davis said four stories he wrote were killed in his time as an editor and freelancer at Vice, including a piece about labor violations at South by Southwest, which eventually ran on Salon.com.

Shane Smith’s one-on-one with Justin Trudeau. Sometimes, Vice News’ content has more in common with legacy news than its own freewheeling roots.

At the time, Vice acknowledged killing Davis’s stories, but said it had nothing to do with conflicts between the news and business sides of the company. “The emails look damning. But the damning thing is there is no centralized policy [for reporting on brands],” said a former Vice employee. “It’s everyone trying to cover their ass and hoping they don’t run afoul of the wrong people.”

Vice has also taken flak for apparently not telling documentary subjects their participation would be used in content sponsored by a company. In one ironic example, a 2012 video about Chicago activists who stop gang fights was sponsored by a videogame whose slogan was “Revenge solves everything.” After Chicago reporter Jason Prechtel outed the story, Vice pulled the video from its website.

Vice walks a thin line between entertainment and journalism; for most of its history, Vice has practiced the former, and now wants to be known for the latter. Entertainment is fundamental to journalism today, expected to smooth our information consumption. At times, the HBO show has resembled poverty tourism, where hipsters romp drunkenly around the third world—the same kind of thing that once riled the late hard-bitten David Carr, who famously excoriated Smith and his colleagues in the 2011 documentary Page One. (Four years later, Carr came around to the company, writing, in the wake of its acclaimed ISIS documentary, “recent events suggest that Vice is deadly serious about doing real news that people, yes, even young people, will actually watch.”) But a more common way Vice entertains is by making correspondents the stars of their segments, which makes them relatable, but can also be self-aggrandizing.

For a 2011 Vice documentary, Shane Smith travels to Libya, meeting the rebels who were then fighting former leader Muammar Gaddafi’s forces, and arrives in the port city of Misrata, more than 12 miles from the frontline. Towards the end of the documentary, creative editing makes it appear that Smith is in a car traveling to what he describes as the frontline although, according to a source with direct knowledge of the production, Smith did not make the trip. According to the source, a sole cameraman went to meet the frontline fighters, even as Smith describes in a voiceover how “we finally got to the front” and “while we were there they got word that a major offensive was about to start.” “It comes down to the edit and the edit at Vice is always about entertainment,” said the source. “There’s no mystery about it: [Shane Smith] is not a journalist, he’s a showman.” Vice did not respond to multiple requests for comment.

In another instance, a former female editorial employee spoke of covering a story involving sex workers in a developing country where she was sent to a strip club. She was also asked to go undercover as a prostitute, which she refused to do. “They wanted to sensationalize and exploit these sex workers in a way that I just couldn’t engage in,” she said. On another shoot, she said, a producer told her to swear more on camera.

Host Kaj Larsen interviews victims of Boko Haram in Nigeria.

This incident points to a complaint raised by some current and former Vice employees: that it remains a boys’ club. Vice’s 2014 media kit showed an audience nearly two-thirds male, and the first season of the HBO documentary did not feature a single female correspondent; three out of 10 correspondents on the latest, third, season are female.

Current and former staffers expressed displeasure that Vice has featured work by photographer Terry Richardson, a longtime collaborator who shot for Vice most recently in 2013, but has been accused of sexual assault by multiple models. The company has since cut ties with Richardson, according to a spokesman. In 2014, graffiti artist David Choe, an occasional Vice host, talked on his podcast about forcing a masseuse to perform oral sex on him, despite her repeatedly saying no. Choe later wrote that the story was fictional and “bad storytelling in the style of douche.” A Vice spokesman said: “We don’t work with him anymore.”

Nancy Ashbrooke, Vice’s global director of human resources, wrote in an email to CJR that sexual harassment has “not been an issue” in the year plus that she has been with the company. “We haven’t had any cases of sexual harassment to deal with,” she wrote. “Honestly, I didn’t quite know what to expect when I showed up at VICE, but the professionalism, respect, and commitment I’ve seen here are outstanding, and on par with or ahead of any other player in the business.”

Through it all, the company carefully guards its public image. For this story I spoke to more than 20 current and former Vice editorial employees and contractors. Many were apprehensive about talking, and some were under nondisclosure agreements signed upon joining the company. Vice’s handbook says that employees are prohibited from speaking to the media unauthorized and “must immediately report all media inquiries from media outlets about the Company’s business to the Communications Director or a Senior Manager before any response is made to the inquiry,” according to Capital New York. Jake Goldman, Vice’s director of communications and a former deputy press secretary for Mayor Michael Bloomberg, arranged, and also staffed, my interviews with two editors and a Vice reporter. For all Vice’s claims of authenticity, it appears the company only wants attention that it has carefully selected.

VICE’S BRAND of video-making is built on a style the company calls “immersionism”—an ostensibly raw aesthetic that resonates with world-weary audiences distrustful of shiny, formulaic programming. So far, it seems that everything to which Vice applies its formula becomes unpretentious. But TV news is the ultimate product of legacy media pretentiousness, a world of dramatized sound bites, smooth transitions and anchors caked in makeup. It couldn’t be further from Vice’s ribald roots.

Right now, Vice News is online only, and editors have stuck to global subjects that resonate with a young audience, such as police brutality, climate change, and student protests. The daily “capsule,” a digest of world news in two-and-a-half minutes, is more likely to mention Chilean salmon harvests than Congressional infighting.

Most news videos are short dispatches, from Ukraine for instance, or 20- to 30- minute documentaries that are often personality-led, with a relatable host in his mid-twenties talking incredulously about what he sees. As the runaway success of true crime podcast Serial showed, a sense of honesty about the reporting process is powerful. In Vice’s interviews, the camera is often on the reporter as well as the subject.

Meanwhile, the impression that everything has been stitched together spontaneously gives the vibe of an inside scoop told to you by a friend, even if the story has already been reported. The video is well edited and shot in high definition like legacy media, but appears informal like social media. In late April, the focus was on the run-up to the UK elections, the aftermath of Nepal’s 7.8 magnitude earthquake, and the streets of Baltimore.

On April 25, protests following the suspicious death of Freddie Gray in police custody turned violent, with some demonstrators smashing car windows and throwing rocks at police. Three days later, Vice’s Monica Villamizar began covering the demonstrations by livestream.

Correspondent Danny Gold answers questions about his reporting in weekly live show On the Line.

There is no anchor to throw to, and no careful composition of shots, only two hours that the viewer spends tagging along with the reporter and cameraman. They talk about where to walk and what shots to get. The camera is shaky, at times out of focus, and the lighting of the street makes a lot of interview subjects’ faces hard to see. But you see the Vice team cold-approach locals, witness a store looting on a street corner, and talk about what shots to get next. It feels rough, but also honest: a peek into how the journalism sausage gets made as much as an insight into what’s happening on the streets.

In this and in four other videos—some more tightly edited to 10 or 15 minutes—we don’t learn much new information about the racial dynamics in Baltimore or the consequences of the protests (although some text reports deal with these issues), but we do get a visceral sense of what the place is like. We see the density of protesters out on the street, and the double middle fingers they throw at police, the shine of sweat on a 32-year-old Baltimore resident who wants the media to leave, and the silent, intimidating line of riot police with batons and clear shields.

The upcoming HBO newscast will be the greatest challenge to Vice’s news reporting ability yet. Nightly news is an entirely different beast from the documentary-making and Web video that Vice’s staff are trained for. It is a rigid format cobbled together under frantic deadlines, and will be the most traditional production Vice has done. The flexibility to circumvent the news cycle and put out content at any length and in any timeframe online will be lost. The technical knowledge to produce daily TV news will have to be learned. And Vice News will have to increase its output from offices around the world. Vice’s best-received story yet was The Islamic State, for which reporter Medyan Dairieh gained an unprecedented three-week embed with ISIS, yet it’s closer in form to one of Vice’s longer documentaries than to a daily news update.

“I think you can still maintain the approach and attitude of Vice News and put that into daily form, and I think that’s exactly what HBO wants, that’s why they’ve come to us,” said Kevin Sutcliffe, EU head of news programming at Vice News. “Clearly the news cycle, the news agenda, will form a very important part of that show. How we manage it, how Vice News approaches it, I think, is the key thing we’re working on at the moment.”

Vice may be known for its edge, but there’s something about news reporting that is inherently cautious and serious. “It is culturally contrary to what Vice has been doing for the last 20 years,” said a Vice editorial staffer. “I wouldn’t say news is the ugly duckling sibling, but there’s a definite difference between news and the rest of the building.”

Danny Gold, an onscreen star at Vice News who reported from Sierra Leone, Guinea, and Liberia in recent months, recounted discussing joining with editor-in-chief Jason Mojica: “I remember asking him, ‘Is this the kind of thing that you want people like my dad to read and to watch?’ And he said yes. That sold me on it.”

Sutcliffe was tight-lipped about how, specifically, Vice plans to translate its web savvy into TV news—“It’s far too premature,” he said—but also hinted that a traditional newscast that supplies 30 minutes of everything you need to know for the day may not be Vice’s aim. “Yes, there is an audience that comes to a particular show at a particular time, but increasingly, people are fully informed during the day because they’re dipping in and out [of the news],” he said. An HBO spokesperson said that president of programming Michael Lombardo was too busy to speak to CJR about the Vice newscast.

News is an important brand-building tool, especially for an outlet trying to shed its bad-boy image. But it is also a commodity. Sutcliffe admits that Vice News entered the market “pre-armed” with a millennial audience from the company’s other channels. “We were pretty sure there was a big audience with a thirst for knowledge about the world,” he said. “They just weren’t being spoken to in a language that meant anything to them.”

Vice News runs pre-roll ads and sponsored shows but Sutcliffe would not say how it makes money, nor if it is profitable. “In the first year, it’s about growing the audience,” he said.

If anyone can get millennials to watch TV news, it’s Vice. But not because the company’s approach to news is especially different. Some of its offerings have a lot more in common with legacy media than the company image would suggest, including the kind of antiseptic one-on-one interviews—with World Bank president Jim Yong Kim or leader of Canada’s Liberal Party Justin Trudeau—that could have run on any news channel. Still, Vice knows how to speak in a language that appeals to its audience. “It’s just being able to tell stories in a voice that millennials can hear,” said Shin of Manatt Digital Media.

PERHAPS THE MOST SIGNIFICANT shift in Vice’s attitude has been from trying to appear trendy—“the hipster’s bible,” as it was known in its magazine days—to trying to seem genuine. Audiences may not trust the mass media, but in an age of crushing information overload, they still need their news curated by a trusted entity. Video that appears to be real hits the viewer viscerally, cuts through the noise of the internet, and shares well on social media.

Advertisers, too, crave the appearance of authenticity, and advertising has historically been at the core of Vice. It may take the form of video ads—the fastest growing form of display ads, accounting for 27 percent of all display ad spending, according to Pew—or sponsorship of entire shows or verticals. Casper Mattresses, for instance, sponsors a podcast on Motherboard, Vice’s technology site, while chipmaker Intel sponsors The Creator’s Project, a vertical on the future of art.

Vice News has for the most part steered clear of sponsored shows, but for The Business of Life, a personal finance show from Bank of America, and On the Line, in which Skype pays Vice to use its technology. On the Line, a weekly, live show on YouTube where people use Skype to chat with Vice reporters about their latest stories, makes Vice appear candid, and bolsters reporters’ star appeal. Yet the only mention that it’s sponsored is a single line, “With support from Skype,” on the Vice News website’s On the Line recaps. The show trailers, YouTube descriptions and, crucially, the live show itself, make no mention of Skype’s sponsorship, even as its logo has been tattooed in the top left corner of the screen every time someone makes a video call. Vice did not respond to repeated requests for comment.

In today’s sponsored content environment, embarrassing tangles between advertising and editorial are not uncommon. BuzzFeed got in trouble in April after killing two stories critical of a Dove soap advertising campaign while Unilever, which owns Dove, has paid for sponsored content on the site. The difference between them and Vice is in the company’s reaction. In the wake of BuzzFeed’s Dove scandal, editor Ben Smith sent a staff memo, which he also tweeted. “I blew it,” he wrote, and reinstated the posts. He and BuzzFeed owner Jonah Peretti also sat down for an 8,000 word interview with Gawker’s J.K. Trotter.

In contrast, when I reached out to Charles Davis, the short-lived former Vice associate editor who handled the controversial NFL boycott piece, he said he still does not know why his stories were killed. Similarly, Jason Prechtel of Chicago web magazine Gaper’s Block said Vice never fully answered his questions about the gang violence interrupters documentary that was sponsored by “Dishonored,” a violent game whose main character is seeking vengeance. At the time, Vice did not respond publicly to claims from the group, Cure Violence, that it hadn’t been told the documentary would be used to promote a videogame. “Vice’s use of a ‘communications associate’ and press spokesperson instead of letting me speak to the filmmakers involved in [the sponsored Vice website] Eye For an Eye is exactly the sort of move you’d expect from a public relations firm, rather than a news outlet that believes in transparency and accountability,” Prechtel wrote in an email to CJR.

For Vice, anything that detracts from its authenticity may not just be an unfortunate bit of press but a strike at the very foundation of its credibility as a company. Right now, the company is thriving: a multibillion-dollar enterprise that continues to be described as “swashbuckling” and “edgy.” That is the irony, and the tension, of Vice. To sustain its appearance of being the genuine article—among employees, viewers, investors, and the media—it needs to be both rebellious and dependable, to have the credibility of The New York Times with the posture of a drinking buddy. Vice must balance these often contradictory qualities as the company strides toward its future as a bona fide media giant.

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Chris Ip is a CJR Delacorte Fellow. Follow him on Twitter at @chrisiptw.

A version of this article appeared in the July/August issue of CJR under the same headline.