Bending the rules promulgated by journalism professors to get a story is nothing new. Think of Tom Wolfe’s Electric Kool-Aid Acid Test or “gonzo” practitioner Hunter S. Thompson—or, for that matter, James O’Keefe’s gotcha line of attack on such varied targets as the Association of Community Organizers and National Public Radio. Yet Neel Shah, who has made himself the subject of a bunch of the stories he’s contributed to magazines and websites, has taken the participatory form to bold new levels.

Even in our all-publicity-is-good Internet era, Shah, 28, seems to have perfected the art of multimedia self promotion, as was evident when on assignment for Radar magazine in 2008. Then his mission was to infiltrate an event called “Natural Selection Speed Dating,” which was open only to men worth millions and women who wanted to go out with them. Shah, an Indian American, pretended to be the “Cumin Baron of Calcutta” and slipped inside with a hidden camera.

Convinced by Shah’s getup, the women inside cuddled up to him warmly. So, too, did the national media. In a move that might shock those same journalism professors who insist that reporters tell the truth, Shah kept up his charade during an interview with CNN reporter Jeanne Moos, perhaps sealing his fate as a journalistic heretic.

After a five-year career of writing for publications such as the New York Post, GQ and Cosmopolitan, Shah has now vaulted into a job in Hollywood as a writer for the sitcom Whitney, which debuted in September. Last spring, having just moved to Los Angeles, he sold a script for another sitcom pilot to ABC Studios. Isn’t this the universe as envisioned by Andy Kaufman, the seemingly always-on performance artist?

“My career path hasn’t been very typical,” Shah admits. It became clear to him that he needed a professional course change because the old way of doing things wasn’t working. “There were no jobs anymore. The whole industry was cratering,” he says of moving from New York City to Hollywood—and from journalism to entertainment.

The oldest of two children, Shah grew up in Port Jefferson, a picturesque waterfront village on Long Island, New York. His dad, Mahendra, is a doctor, and his late mom, Rita, was a medical technician. His sister Sona also became a doctor, meaning that Shah was the creative-minded “black sheep” in a family of scientists, he says. Still, his parents encouraged Shah—who used to devour Mad and New York magazines, as well as Seinfeld—to pursue his writerly ambitions. “They were pretty liberal for Indian parents,” Shah says.

As a student Shah, a government major and English minor, wrote a few pieces for The Dartmouth, including a satire about the lack of couture in Hanover, as well as posts for the “Generic Good Morning Message,” a popular daily e-mail. Unlike many alums who tend to play up the virtue of their out-of-classroom activities to boost employment potential, Shah proudly and somewhat refreshingly embraces his undergraduate slackerdom. “I generally didn’t do anything,” he says, without a trace of guilt. “I hung out and enjoyed my time there.”

Josh Pence ’04, who roomed with Shah off-campus on West Wheelock Street and is now working as a Hollywood actor, is more blunt: “Neel was committed to being the life of the party, at every party, and that’s a full-time commitment,” he jokes. Pence has a fond memory of discovering his housemate, after a few beers, asleep in their apartment in the arms of a giant stuffed dog, smiling.

Shah’s first big break came while trolling the web during sophomore summer in his room in Alpha Delta, when he stumbled upon the gossip website Gawker. A few e-mailed work samples later, Shah became a regular contributor. Highlights from that time included penning to-do lists about how to spend a weekend in New York—despite the absurdity of his living hundreds of miles and a world away from the city—as well as recurring opinion items about Ivy League high jinks.

That gig led to an internship the next summer at the New York Observer newspaper, where Shah added to his clip file by covering events such as the anniversary party for High Times, the glossy magazine that celebrates the wonders of marijuana. Hooked on the buzz of seeing his byline, Shah after graduation decamped for Manhattan’s bohemian East Village and took a full-time job as a writer for the website College Humor. (Recent articles posted on it include “25 Most Embarrassing Things in the World” and user-submitted videos such as “English Mastiff Caught Red-Handed.”)

Around the same time Shah co-wrote a self-help parody called Faking It, which Penguin published in 2007. On its cover is a photo of malt liquor being poured into a wine goblet under the subtitle, How to Seem Like a Better Person Without Actually Improving Yourself.

The intrepid one-man media machine also dabbled in television and video. There was his appearance on The City, an MTV show, and another on the screens in the backseats of New York City taxi cabs advertising the search engine Bing.

Shah’s willingness to push the envelope in terms of funny stunts grew more inventive, as at Radar in 2007, when he tried to determine if cocaine use had lost its social stigma by snorting powdered sugar in full view of the public at various high-traffic locations. One was the reading room of the New York Public Library, where Shah, wearing dark sunglasses and gold chains, “was accosted by a mother reading Harry Potter with her kid,” he says.

Shah often indulged his sensitive side, too, auditioning—albeit unsuccessfully—to be Glamour’s dating columnist, arguing that he was qualified based on his own vast experience. How many dates exactly? “Oh my god, I don’t know,” he says. “It was an exhausting five years in New York.”

Not surprisingly Shah’s unique approach to journalism occasionally landed him in hot water, such as the time he was called out in reader posts and beyond for a story he penned for The Awl, a pop-culture website, that said women will often try to skip out on the dinner check with a line like  “ ‘Oh, I forgot my wallet,’ ” he laughs. “For some reason, it struck a nerve.”

In 2009 came a job that seemed a perfect storm of his interests: a gig with the New York Post’s “Page Six” gossip column. Unlike some entry-level reporting gigs, this one did not require sitting through zoning board meetings. Instead it meant pin-balling between fashion shows, bars and baseball stadiums to dig for salacious items about actors, newscasters and athletes. Night after night and often till dawn, Shah, by his own admission, was deep in his element. Often he appeared to be as stylish—his outfits included plaid shirts worn trendily tight along with knitted caps—as the A-listers he was covering. A quick google search of his name seems to turn up just as many photos of Shah, some posed with N.Y.C.-party-circuit mainstays, as bylines.

J.J. Hunsecker, the gossip columnist in the 1957 film Sweet Smell of Success, may have loathed the scheming press agents who tried to get him to write about their clients, but Shah in many ways literally put his arm around them.

If Shah was a night owl in New York City, the West Coast seems to have clipped his wings. On a recent Saturday night he shows up for dinner at Jitlada, a Hollywood Thai restaurant located in a strip mall along a forlorn, and thus cool, stretch of West Sunset Boulevard. Inside the dining rooms, whose ceilings are lined with colored lampshades, are groups of post-college-age diners wearing retro eyeglass frames. Shah, wearing a dark-blue shirt with wide collar, white pants and sneakers, asks if it’s okay to order for his guest. The multi-course event that unfolds includes a bowl of green-shelled mussels along with a mango salad with cashews, plus a sea bass in red curry sauce that arrives whole on a plate. “There were a lot of late nights in New York, though I never had a job that started before 10 a.m. Now I’m in bed at 1 a.m., tops,” says Shah, in quiet, easy cadences, as he pushes a fork into the fish. Single and still able to train a sharp eye on the mating rituals of modern 20-somethings, Shah complains that dating in L.A. is way too much work. In New York City “you run into people or you can text them to meet up,” he says. In L.A. “you have to go on formal dates, which can be expensive and exhausting.”

Notably, a man who once wrote about the beneficial effects of alcohol on dates finishes just half of his bottle of Tsingtao beer. Despite many entreaties to continue the evening in a champagne-buckets-in-a-limo kind of way, as used to be Shah’s wont, he politely says good night after the check is paid.

Shah’s second big break came in 2010. While working for the Post and covering events in Manhattan’s meatpacking district, Shah met Brad Grossman, who had once worked as a “cultural attaché” (basically a researcher) for Brian Grazer, the mega-producer who has won Emmys for Arrested Development and 24 and an Oscar for A Beautiful Mind. As it turned out, Grossman’s old job was open. A few years earlier, when the position was previously available, The New Yorker ran a story about it and quoted the e-mail ad making the rounds at the time: “This person would be responsible for keeping Brian abreast of everything that’s going on in the world; politically, culturally, musically. They’re also responsible for finding an interesting person for Brian to meet with every week…an astronaut, a journalist, a philosopher, a Buddhist monk.”

Grazer flew Shah to L.A., then grilled him in a large TV-lined office for hours, with a lot of time spent on the topic of the future of media. Though the job did not materialize, the interview did lead to an important connection at Imagine Entertainment, a movie studio looking for ideas for a show about young people’s dating habits, currently a popular Hollywood topic. Shah sent a producer at Imagine 15 dating stories about himself and friends, including some hook-up tales from Dartmouth. The list includes Sex and the City-esque anecdotes about a man insisting that a couple sleep a certain way to align themselves in the direction of his native country, a guy who cooks a dinner for a date that is so bad it leads to her food poisoning, and a girl who lets her smelly Yorkshire terrier come a little too close for her date’s comfort.

A few weeks later the call came in: an invitation to write for Friends with Benefits, a new sitcom executive produced by Grazer. Within days Shah packed his Lower East Side loft and shipped his car west to become a Hollywood writer. Ultimately, the comedy did not survive Comcast’s takeover of NBCUniversal, becoming just one of many shows never to make a network’s lineup. “We thought it was a fun show, so for it to get no shot at all was tough,” Shah says. Yet he stuck around town, hammering away on his own script for that pilot he sold to ABC in 2011. It’s a “post-racial dating show about Indian Americans,” he says.

As if selling the first show he ever wrote wasn’t enough of a coup, Shah also landed the writing gig with Whitney, which airs Thursday nights on NBC. One of 10 writers, he is employed to do what most people probably imagine television writers doing: sit at a table in a small room, batting around ideas. “There are pencils stuck in the ceiling. It looks like a producer’s version of what writers’ rooms should be,” he says. “Sometimes you are shocked that you are getting paid.”

The show’s first episode, of 13 originally commissioned, was written solely by its star, stand-up comic Whitney Cummings, though the salty dialogue seems pure Shah. To wit: “Cosmo”—as in Cosmopolitan, the women’s magazine Shah once wrote for—is “for skanks,” Cummings declares in one scene. In another she points to herself and playfully asks her boyfriend Alex, “Why aren’t we tapping this?” Shah can claim partial credit for a line uttered by Whitney in the second episode: “You should update your Facebook status to make him jealous.”

Early reviews of the show were mixed. Alessandra Stanley of The New York Times called Cummings “comically abominable, so abomical” after an early viewing, but she went on to write that the show has moments and that the star is often a “pleasure to watch.” Although viewership dropped by about 1.5 million people between the first and second episodes, in early October NBC ordered nine more episodes, bringing the grand total to 22—a full season.

The time Shah has logged on the dating world’s front lines, plus the fact that he’s one of the few writers on the show who is single, helps nail the tone, according to Cummings, who adds that he’s also a cut-up during brainstorming.

“He tells us his crazy stories, which are a mix of hilarious and alarming,” says Cummings. “He teaches us all the new slang and social networking sites, and I am pretty sure he tweets about 300 times a day from the room.” (Actually, although he is a presence on Twitter—@fneel—it’s not to that extent. At least not yet.)

Indeed, with references to Blackberries, texting and Angry Birds sprinkled throughout Whitney episodes, the show does seem to wear its tech-savviness on its sleeve. “It’s really important that people on the show talk how people at 30 actually talk,” says Cummings, 29. “Neel is our reality police who is like, ‘He would know that because he googled her’ or whatever, which is a great instinct on his part.”

Away from the writers’ room, Shah appears to have taken to his new digs nicely. Pence recalls showing up recently for a party at Shah’s house in L.A.’s Hancock Park neighborhood to find actress Zooey Deschanel in the living room. “How do you know this many people after just being here a month and a half?” Santa Monica, California, native Pence recalls asking Shah at the time, incredulous. “People just get such a kick out of him.”

Shah, meanwhile, is confident that even if Whitney is canceled, his own particular take on the fourth estate—both insouciant and confidently self promotional—was the right call. “I’ve finally figured out what I want to do,” he says, “and I’m pretty stoked.”

C.J. Hughes is a contributing editor. He lives in New York City.