In June 2009, Weingarten gave a very short speech at the 140 Characters Conference, a two-day gathering of Twitter users and enthusiasts in midtown Manhattan. Rick Sanchez, the spirited CNN reporter, was there; so was Ann Curry of NBC; so was Wyclef Jean. In keeping with the medium’s inherent brevity, no speaker was allowed to go for longer than ten minutes. Weingarten’s topic was the Internet’s effect on music criticism, and, from the top, it was clear that he had no interest in pandering to his audience: “I am Christopher R. Weingarten. I am a freelance writer for Rollingstone.com, The Village Voice, Revolver magazine, Decibel magazine, [the Web site] Idolator, and more. By this time next year, I’m going to need a new job.”

He went on to speak about how the Internet was destroying decent rock criticism; how the tide of online enthusiasms tended to elevate not the best music, but the music the most people could stand; how, without professional critics to champion legitimately praiseworthy material, that material would never find an audience. “If you let the people decide, then nothing truly adventurous ever gets out, and that’s a problem,” he said, pounding the podium for emphasis.

The speech drew cheers from the crowd, but Weingarten thinks it likely that, rather than cheering his message, they were simply excited to hear “a lot of apoplexy and swearing.” He was serious, though. “If I could wave a magnet over the whole Internet, I would do it in a heartbeat,” he says. “We all wanted to democratize art. And now that we did, nobody’s making money off of art, and art’s not as good.”

The trend toward musical mediocrity, he thinks, is epitomized by the blogosphere’s adulation of guitar-rock bands—“This boring, bland, ‘white people’ guitar music. It fucking sucks. I hate it. This NPR bullshit”—and singer/songwriters like Conor Oberst and Iron & Wine—“James Taylor for people with hoodies.” In bands like these, largely popularized by the Internet hive mind, he finds nothing interesting, nothing daring, nothing necessary.

He often takes refuge in older music. He is currently occupied with acquiring every hip-hop record released between January and December of 1988, which he insists was rap music’s miracle year. He hits one hand into the other, giddy with delight as he lists some bands whose records were released that year. “Public Enemy. N.W.A. Slick Rick. DJ Jazzy Jeff & the Fresh Prince. God, the Marley Marl record. The Kid ’n Play record. It was this period when rappers were still experimenting—Sir Mix-a-Lot! 2 Live Crew! Rap was selling and the studios didn’t know why. It was like the movie studios before Jaws.”

Every couple of months, he spins a set of 1988 hip-hop at a local bar or club. He is proud of his DJ skills, to a point. “I could make it flow, and make it bleed, but I don’t really know who the audience is,” he says. “I think people want to hear music they know, not Krown Rulers. I had this girl come up to me and say, ‘Can you play something I can dance to?’ I thought, ‘If you can’t dance to hip-hop, then the music is not the problem.’ Maybe it’s me.”

He continues to review new records on Twitter, although this year he’s not going to force himself to do a thousand. And while 1000TimesYes has brought him exposure and writing opportunities, his financial outlook remains grim. Formerly the drummer in the experimental Brooklyn band Parts & Labor, he has barely played music since 2007, largely because he cannot afford to rent a practice space. He has no health insurance. He collects receipts for all expenses that are even remotely work-related, in hopes of some future reimbursement check or tax deduction. Still, he has defied his #140conf prediction of impending unemployment. “I think I’ve got another year in me,” he says. “Whether I’ve got another two years? I don’t know.”

“Does anyone have a GPS?” it’s the second day of this year’s South by Southwest conference (SXSW) in Austin, Texas. Weingarten is sitting in the back of a pedicab, on his way to see the rock band Quasi play an afternoon set at a club called Cheer Up Charlie’s, and the pedicab’s driver is hopelessly lost. “I’ve lived here for twenty years,” he explains. “Never heard of that street.”

Weingarten fumbles with his mobile phone. “GPS is fucking terrible in this town,” he says. “In every town, really.” Quasi is scheduled to go on at 4 p.m.; it’s now about 4:40. Weingarten shrugs. “If we don’t see Quasi, we’ll see the next band.”

Justin Peters is editor-at-large of the Columbia Journalism Review.