LOLLIPOP wasn’t always about Scott Hefflon. In fact, it wasn’t even his idea. The Connecticut native, who spent five years at four colleges earning a two-year architectural degree — "The only thing I learned was how to stay up all night" — was working in a liquor store when friend Karen Granaudo suggested they start a music ’zine.

This was 1993, a year after USA Today declared the onslaught of a " ’zine revolution." But Hefflon, who’d rather be a dead man than a follower, insists he wasn’t being trendy. "Truthfully, I didn’t know it was the thing to do to run a ’zine. It was just something to do for my circle of friends." His circle of friends included only one person with an English degree, Laura Kallio, whose college credentials made her the default copy editor, and Dave Dawson, a MassArt grad who became graphic designer. None of them really understood the mechanics of making a ’zine — design, layout, printing, distribution — so they got acquainted with Kerry Joyce (who would later marry Kallio), a writer who had freelanced for the Worcester Telegram & Gazette and published two issues of his own humor ’zine, Core. Joyce offered his print experience and production expertise to help Lollipop become a reality.

The first issue was 32 black-and-white newsprint pages with a color cover and one advertisement, a quarter-page promoting The Witches’ Almanac. That ad brought in $100, but the print bill totaled $1200 for 5000 copies, and Lollipop lost $1100 on its first issue. Although the second issue sold $500 worth of advertisements, Hefflon didn’t keep the money to recoup initial losses; instead, he doubled the press run to 10,000 copies.

Although Lollipop was intended to be "an edgy, flamboyant ’zine covering sung and unsung heroes from all over New England," as Hefflon remembered in the third-anniversary issue, its identity was defined by its raw, irreverent style more than its subject. As more and more issues hit the streets, it became a swaggering paean to hard living, hard drinking, and hard rock, a pamphlet of restless, rambling prose that continually lashed out at the mainstream. "We wanted to print some wild, crazy, profane, edgy shit," recalls Hefflon. "Say the word ‘fuck’ every so often — we say it in our regular lives, why can’t we say it in the magazine?"

Critics said it was juvenile, self-indulgent, and sloppy. Hefflon didn’t care. With the help of his staff, he kept putting it out. In addition to record reviews and live-show reports, Lollipop contained fiction, essays, and rants. It also came out monthly. ("I have no fuckin’ idea how it came out monthly," Hefflon says. "Now I’m almost a month late sometimes.") And it differentiated itself from other music publications like the Noise and Boston Rock by featuring intricate, striking color illustrations on its covers.

"It was always much more eclectic than the other ’zines," recalls former fiction editor Kerry Joyce, who finally ended Core to spend several years working with Hefflon. "Other ’zines didn’t really understand Lollipop. They really had this idea that ’zines functioned to support the local scene. And we never really had that attitude."

Although Hefflon was essentially at the helm, there was a makeshift community of creative types at Lollipop’s center who didn’t, in the words of Joyce, "connect with anyone else" — wanna-be writers and visual artists who weren’t refined enough to get full-time gigs in their respective fields and were simply happy to see their stuff in print. And every month, there were contributors’ parties. Lollipop alumni tend to speak about these events in reverential, awestruck, nostalgic tones. For most, the memories are a haze of nudity, liquor, and other unfit-for-print indulgences.

Even the "office," Hefflon’s apartment, was a regular hangout, the kind of place where, as Lex Marburger wrote in the third-anniversary issue, "people were stretched out on every conceivable piece of furniture." Eventually, Lollipop became established enough to get real office space in a corner of Davis Square, above Mike’s Restaurant. People were there from the morning until early the next morning. "It was a really stimulating, exciting, fun place to be," remembers Joyce.

But Hefflon was the gas in the engine, the flint that lit the fire. "Outside of the core players, we were a ragged collective of individuals with no real vested interest," recalls former contributor David "Austin" Nash, one of the ragged ones. "It was the way Scott struggled to put it together. He and the others ran a mostly disorganized group that pulled together like superheroes at the end of a month to get the job done."

And Hefflon did get the job done. A former telemarketer and bill collector, he was such a successful salesmen that Lollipop stayed in business and went national for issue 20. At one point, Lollipop’s circulation even reached 30,000 a month.

But though Hefflon is directly responsible for Lollipop’s successes, he’s the first to admit that he is also its tragic flaw. "I always say that Lollipop’s biggest problem is that it’s run by me."

SCOTT HEFFLON wants you to know that he’s doesn’t care about anybody but himself. "Everyone is always second to me," he likes to say. He also wants you to know he doesn’t value your opinion. "Other people’s opinions mean far less to me than my own. If I think what I’m doing is right, every single person I know can tell me that it’s going to blow up in my face, and I can say, ‘Fine, don’t back me. I’m not asking you to back me. I wasn’t asking your permission, I was telling you what I was doing.’ " He claims he won’t compromise for a paycheck. "Money comes and money goes, and compromise stays with you. When you’re talked into something that you don’t want to do, that sticks with you. The check clears and then you spend it and then it’s gone. But knowing that you got talked into doing something, you just feel dirty, and I’m a dirty enough bitch as it is." And he’d like to add that he’s a bad manager. "I don’t give advice, I don’t lead, and I don’t tell people what to do.... Interns always get really frustrated with me, because I don’t really direct them."

"Scott’s a dick," says Laura Joyce. "I wouldn’t describe him as lovable, mellow, or easy to get along with. But the qualities that make him so difficult are what’s kept Lollipop alive."

Hefflon also nearly killed Lollipop more times than he can remember. Probably the closest the magazine ever came to dying was after its fifth anniversary, when Hefflon had accrued so much debt that he had to lay off the whole Lollipop staff, shut down the Davis Square headquarters, and move the magazine back to his house. "I do things out of ego and not business sense," he states. "I refused to admit that I was hemorrhaging money." It took him a year and a half to remit his debts, but he did it eventually.

As far back as issue two, Hefflon’s single-mindedness corroded relationships, and, in turn, nearly destroyed the magazine. In the beginning, he and Dave Dawson had been collaborating so intensely on producing Lollipop’s first two issues that Hefflon was practically living at Dawson’s house. "Scott is a very intense person," says Dawson. And after dealing with Hefflon so closely for so long, he couldn’t handle it anymore. Dawson came close to a nervous breakdown. "I was like, ‘Fuck this.’ I went and got a real job."

Although he returned around issue 30, Dawson wasn’t the only one Hefflon drove away. "Illustrators quit pretty often," he says. "And illustrators also get paid five times what writers get paid, and writers get paid $5 a CD review. To me, it’s like, ‘You’re an illustrator. Dude, you draw. Your notebooks should be filled with stuff. It’s not a fuckin’ higher art. It’s not gold. Whip off an illustration and I’ll give you fuckin’ $25 for it. What’s the big fuckin’ deal? You want 500? Why?’ "

"A lot of people were openly disdainful of him, and he didn’t really mind," says Kerry Joyce. "His ego is so big it doesn’t really bother him." Even Joyce has nearly abandoned Hefflon a couple of times. "There have been a few times that I’d say that I’m never going to see Scott again. But I know he’d enjoy that too much. I’m going to be his friend out of spite."

So why-oh-why do people continue working for him? "That’s a good question," Hefflon says, uncharacteristically at a loss for words. "I don’t know." He chews on the thought for a few seconds. "To get some free stuff and not have their stuff hacked to pieces?"

But the bigger question is, how has Lollipop survived? "I have a short answer," says Dawson. "Scott refuses to quit."

Hefflon himself responds differently every time he addresses the question. Once, he explains that he used to focus all his energy on getting girls, but instead decided to put that same energy toward advertisers, and that’s what’s kept Lollipop afloat. In the editor’s rant published in Lollipop’s upcoming 10th-anniversary issue, he points to the fact that he does little else besides run Lollipop. "When people see that a scraggly, sharp-tongued little shit like me actually consistently pulls together a nearly 100-page glossy mag, they overlook the fact that I’m wearing the same clothes as the day before, and that my fridge is empty and my sink is full." Another time, he credits his indifference to money. "I don’t really care too much about money. That helps. I figure I’m only going to spend it on booze and lap dances anyway."

FOR THE FIFTH or maybe the 70th time in the course of five or six conversations, Hefflon is bragging about how many people left the magazine, stormed out of the office in a huff, hate him, think he’s an intimidating prick and a dick and a few other bad words. So finally, the question is posed: is having so many people walk away a point of pride? "Well, I’m not going to be nice," he says, exhaling smoke into the receiver. "Actually, I think I’ve gotten nicer. Only recently did I learn the phrase ‘I’m sorry,’ " he brags. "And I started writing the word ‘thanks’ at the bottom of e-mails — that’s new to me."

Then, as always, he digresses into a harangue. "See, [writers] are always asking me if I read their piece and what I thought of it. It’s like, ‘What? You want a pat on the back, go get a friend. I’m your editor. I print your stuff. I keep printing you and I keep writing the checks to pay you. Y’know, if you need more validation in life than that, find it elsewhere,’ " he sneers. "That’s your compliment — the fact that I haven’t fired you."

There’s silence on the phone for about five seconds and he hears his interviewer laughing. "Sorry," he mutters. Six more seconds elapse. And then, a different side of Hefflon peeks through. "All right, so there’s a lot of self-defense bullshit going on [with me]," he concedes. "A lot of the stuff I say is meant to keep people at bay." He sighs. "I’m more or less like this anyway, but this whole persona thing was built for a reason and is maintained for a reason. And it’s fun. It’s fun to have people come up and say, ‘Man, you’re not the monster everyone makes you out to be.’ [But] really, what’s the sense of being in my position if I’m just this mealy-mouthed little guy who says all nice things about all people? That’s no fun."

But in less than 30 seconds, Scott Hefflon is back to his old self. "Did you talk to Laura?" he asks. "She’s a professional bitch."