With his pink wardrobe, adoption of retro video-game character Sonic the Hedgehog as a spirit animal, and languid verses, Charles Hamilton was a newcomer built to thrive in a rap environment that has learned to tolerate a splash of DayGlo whimsy. The 21-year-old was cute and contempo and sensitive, but retained enough Harlem arrogance to escape being ostracized as a total pussy. After signing with Interscope Records in the summer of 2008, Hamilton spent the next year exuberantly building a reputation as an underdog smartass: He released several mixtapes, blogged with regularity, Twittered 50-some times a day, and reveled in the real-time furor he was able to create as a hip-hop fameball.

Despite Hamilton's enthusiasm, missteps accumulated. He was busted for pilfering a beat from an underground producer. He came out the loser after exchanging disparaging video clips with kiddie-rapper Soulja Boy. He was punched in the face by a female spoken-word poet after insinuating that she had aborted their unborn child during a videotaped "battle." And in a climactic faux pas in June, he weirdly credited deceased beatmaker J-Dilla with "executive producing" his forthcoming LP A Perfect Life—a sin that earned self-righteous rebuttals from protectionist Detroiters and a refutation from Dilla's mother. Within a week's time, Hamilton vanished from the Internet: no blogs, no Tweets, no videos. (His last Twitter update, dated June 10: "Good morning sunshine!!!") According to industry rumormongers, Interscope honcho Jimmy Iovine himself issued the gag order: Shut your pie-hole, or lose your deal. (Hamilton declined an interview request for this story.) A life and death done digitally, this was the rap version of a Tamagotchi pocket pet.

Whether this online exile was self-imposed or commanded from on high, his rise and fail are indicative of the alternative outcomes that can occur when an artist dives headlong into the virtual fishbowl. As record sales wither and labels strain to monetize artists as shampoo-shilling "personal brands," online outlets such as blogs, Twitter, and video channels like Vlad TV and World Star Hip-Hop have taken on increased importance. Seldom inclined to shy away from attention, rappers have discovered that these are ideal mediums for beefing with rivals, griping about the music business, threatening retirement, and otherwise piling firewood onto the roaring bonfire of their egos. Once muzzled by publicists, promoters, and management intermediaries, they're now free to grouse, giggle, and emote in real-time. "Artists are feeling more empowered with the technology," says Elliott Wilson, former editor-in-chief of XXL magazine who currently runs the Rap Radar site. "You can tell people not to do XYZ, but it's so easy to get your message out there. It just takes you a second to type a couple thoughts." As a fuchsia-clad Harlemite can attest, the ever-thinning membrane between celebrities and the public can be a gift and a curse.

Hip-hop artists immersed themselves in social networking just like everyone else: A few pioneers recognized the potential, and the clueless masses blundered in later. ?uestlove, El-P, and Prodigy of Mobb Deep were prescient enough to become active on their own websites or message boards early on, but a digital wall manned by label sentinels usually separated artists from the general public. MySpace, a site expressly created to splinter such barriers, was the next major step: Those clunky pages (excellent as they were for aggregating groupies) have given way to an environment in which an independent artist with a strong online presence can compete for face-time with acts on major labels.

Consider New Jersey rapper Joe Budden, a former Def Jam signee who now wedges himself into the news cycle with remarkable consistency without that association. He indulges in feuds with other artists, uploads video of his buxom girlfriend to the Joe Budden TV site, and is part of Slaughterhouse, a group that includes several other artists (Crooked I, Joell Ortiz, Royce Da 5'9") more popular in the blogosphere than on the radio. He even briefly crossed into the world of basketball after streaming footage of an expletive-laced phone conversation with Milwaukee Bucks draft pick Brandon Jennings. To Budden, the key to captivating an online audience is simply authenticity: "Over the years, the fans have gotten a lot wiser," he says. "They can tell when it's not the actual artist or it's just someone doing it for the sake of doing it. When it's genuine, it's way better."

Assuming their digital incarnations aren't bored interns or multitasking weed-carriers crumbling Kush on a MacBook, artists take divergent approaches to promoting their music and interacting with fans. Diddy, who survived a #unfollowdiddy campaign on Twitter in May, has corralled over 1.6 million people intrigued by his exclamation-point-spiked exhortations for positivity and praise for Ciroc Vodka. He's not sending out tweets while dodging Basij bullets on the frontline of the Iranian protest, but for Diddy, it fits.

Even artists less prone to taking bubble baths with their Grammys can complement an on-record image by being interesting online. "Personality goes a long way," says Phonte, a rapper in the group Little Brother who posts on Twitter and the Okayplayer message board. "There is nothing more boring than a PC milquetoast-ass nigga. A little well-placed snark and humor can help people see you in a new light—it shows you are capable of critical thought and enjoy spending time among the commoners in the peanut gallery."

A personal touch is attractive, but not when it veers into inappropriate humor or cringe-worthy oversharing. Earlier this year, white frat-rapper Asher Roth was demonized for making an ill-advised tweet about "hanging out with nappy headed hoes," while Kid Cudi penned a blog post claiming that the toll of celebrity was forcing him into premature retirement (unsurprisingly, he walked it back). The ease of blogging or Twittering begets a flippancy that may look even cheaper under scrutiny. "Rappers will make a bad joke or just have a bad day and express their frustration, and it becomes a heavily circulated story," says Wilson. "If you write some Twitters where you're just like, 'I'm feeling real depressed today,' then everybody has you on suicide watch. Sometimes, artists don't realize that everything they say on their Twitter page is on the record."

As blustery and sensitive a breed as they might be, rappers are not the only celebrities who have found social networking a mixed bag. In July, Nine Inch Nails frontman Trent Reznor deleted his Twitter account after he and his girlfriend were repeatedly harassed by, as he put it, "unattractive plump females who publicly fantasize about having sex with guys in bands." Outside of music, Dallas Mavericks owner Mark Cuban was fined $25,000 for criticizing NBA officials on Twitter, while Pete Hoekstra, a U.S. Representative from Michigan, inadvertently revealed his location while traveling through Iraq and Afghanistan. Rule of thumb: Think first, post second. "Arrogance, negativity, and emotional rants where artists are complaining about private and confidential matters can cause issues," says Tracy Nguyen, a publicist who has worked with Nick Cannon, Kelis, and Ice Cube. "It can result in the type of press attention that perhaps they aren't seeking." Of course, if you live by the adage that all publicity is good publicity, you have nothing to fear—except maybe Jimmy Iovine.

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