How a pudgy Miami poseur became gossip's new queen

It's 10:30 p.m., and Mario Lavandeira—or rather, his online alter ego Perez Hilton—is 30 minutes late to the AOL Style Lounge on the outskirts of the MTV Video Music Awards site in Manhattan's Rockefeller Center. Here vendors give away cologne, liquor, clothing, shoes, jewelry, accessories, and even real, permanent tattoos to any famous person who will take them—or to Perez (assuming he shows), who is virtually guaranteed to plug the products on his blog. When one non-famous passerby attempts to score a free pair of D&G shades, though, a polite PR princess tells him firmly, "We're only gifting to talent."

"I'm an insider, but I'll always be an outsider"Then Perez arrives. Six-foot-two with grown-out bleached-blond hair styled in a faux-hawk, he's dressed like a caricature of a Hollywood It boy, in a soft pink blazer with the word arrogant embroidered down one sleeve, a graffiti-patterned T-shirt, sagging, intentionally ragged jeans, and matching pink slip-on Vans—"a very Perez outfit," Lavandeira, 28, says later. "Mario would never wear that." He's doughier than many of his pictures suggest and considerably sweeter in person than readers of his celebrity-skewering blog, perezhilton.com, might expect. Floating from booth to booth, he doles out generous attention to anyone who says hi. As he wanders across the room, scores of publicists flock to his side, stuffing his weekender-size tote bag with free products. Over the years, Lavandeira's vocation has earned him everything from Xtreme Lashes mascara to a T-Mobile Sidekick, which he reliably plugs in a category of his blog called Schwag Report. At the D&G table, he scores a free pair of shades worth about $400. "The gold ones," Lavandeira trills later, noting that they're the same kind Snoop Dogg sports. "I wore them for my Getty Images portrait."

Dubbed "Hollywood's Most-Hated Website" by Pat O'Brien's Insider, perezhilton.com is cotton-candy-pink junk food for millions of celeb-hungry Web surfers. Most come for the candid photographs leaked to Lavandeira by the paparazzi or lifted from other websites (he rarely shoots and almost never pays for images), to which he adds captions and digital scrawls in the style of a 14-year-old with a Magic Marker: a drawn-on pee-pee near Clay Aiken's mouth, or white dots meant to represent cocaine under Lindsay Lohan's nose. In addition, the self-proclaimed "Gossip Gangsta" and "Queen of All Media" incorporates tips he gets from celebrity magazine sources and others into bitchy, shoot-from-the-hip rants studded with snarky nicknames. He's dubbed Kevin Federline "K-Fag," Clay Aiken "Gayken," and Nicole Richie "Baby Zahara" (a seemingly racist allusion to Angelina Jolie's adopted Namibian child). His shining moment involved several "exclusive" sightings of former *NSync member Lance Bass at gay hangouts. Bass officially came out on the cover of People weeks later. Lavandeira, who is openly gay, casts a wide net of speculation, though, and similar insinuations about the sexuality of Lance Armstrong, Jake Gyllenhaal, Matthew McConaughey and Kyle XY star Matt Dallas (whom he calls "Kyle KY") have yet to pan out. Dallas did, however, go on Howard Stern's radio show recently to declare his heterosexuality. Remarkably, Lavandeira has never had to go to court over a post. "I'm more trustworthy than Page Six," he brags, but a prominent disclaimer on his site suggests otherwise: "Postings may contain erroneous or inaccurate information. The owner of this site does not insure [sic] the accurateness of any content presented on perezhilton.com."

His accomplishments, such as they are, are all the more notable given his inauspicious history. The son of Cuban parents, Lavandeira was a self-described "fat, gay kid in Thespian Society" at Belen Jesuit Prep in Miami before moving to New York in 1996 to become an actor. Instead, he wound up making ends meet by working as an assistant to a club DJ, tutoring students in Spanish, babysitting, handing out flyers, and "for one hot second," as he puts it, bartending at Broadway theaters. He graduated from Tisch School of the Arts in 2000, but aside from some extra work on soap operas, The Sopranos (playing Male Student in the 2001 episode "Fortunate Son"), and a NY 1 cable network ad, his acting career was a bust. So in 2002, Lavandeira moved to L.A., where he worked at a boutique PR firm and began freelance writing for local gay publications. In 2005 he returned to New York to work as a reporter for Star magazine, but was fired after a few months for spending too much time on a personal project—a blog, which he had started in September 2004. Star considered the blog a conflict of interest since it relentlessly ripped into stars Lavandeira might cover for the magazine—from Christina Aguilera to Christina Ricci. Plus, the site was starting to get lots of attention, due in part to its catchy name, pagesixsixsix.com.