You really couldn’t mistake him for anything other than a professional critic. Part of it’s the look—headphones, music-themed apparel, thick glasses, heavy beard—as if he just stepped off the set of the movie High Fidelity. But it’s mostly the enthusiasm; the cultural excitations that can prompt blunt, rapid-fire disquisitions on the things he likes (hip-hop, the CD format, the critic Chuck Eddy) and the things he does not (Fleet Foxes, singer-songwriter music, the comedians Tim and Eric). He is the sort of person who not only brags about his world-class collection of Christmas rap music, but will forcefully argue the musical merits of certain items from that collection; the sort of person who, when attending a weekend music festival, will try to see all forty-six shows on the bill. He did this in 2008, in rural England, at the All Tomorrow’s Parties festival co-curated by Mike Patton and The Melvins, an experience he calls the greatest weekend of his life. “It was very difficult. My feet were sandbags at the end,” he admits. But, on the other hand, “The Melvins are my favorite band in the world. I didn’t want to miss this day of music that they co-curated.”

Weingarten is thirty. He grew up on Florida’s Gulf Coast and studied journalism at the University of Florida, in Gainesville. There, he wrote about music for the student newspaper, the Independent Florida Alligator, and fronted a band called the Christopher Weingarten Basement Funk Allstars, where he was known, according to the Web magazine Ink19, for “running around like a maniac, hilariously insulting the audience” and “playing the roto-toms, keyboards, and yes, the Theremin.”

After finishing school in 2002, he quickly made his way to New York, where he set about finding work as a music writer. While “rock critic” has never been a particularly lucrative career choice, it made much more sense back then—there were plenty of outlets for which to write, and reviewers could supplement their income by reselling the advance CDs that came in the mail. (“I do not get as many records as I used to. Labels are sending less CD promos every year,” he complains.)

From 2002 to 2006, he held various positions at CMJ New Music Monthly—intern, associate editor, editorial coordinator, music editor—where he wrote features, reviews, and columns, before leaving to edit a new Web site called Paper Thin Walls. Unlike some other music sites, Paper Thin Walls—which was purchased by Getty Images in 2007—made a point of paying its contributors; because of that, the site attracted several well-known names—Frank Kogan, Michael Azerrad, and Michaelangelo Matos among them. “We had all the best writers,” he says. “We paid writers what they’re worth to write.”

Perhaps predictably, the site shuttered in September 2008, and Weingarten left music writing behind for a while, taking a job writing for a celebrity photo and gossip site called Jamd. The work didn’t suit him, and he was laid off soon thereafter. “I didn’t feel right doing it,” he said. “I don’t feel right doing anything I’m not passionate about.” It was around this time that he started his Twitter account.

When Weingarten began the 1000TimesYes project in January 2009, he was out of professional music writing, on the brink of unemployment, and looking for a way to rejoin the critical conversation. By the time he reviewed his final record of the year, on December 22 (“1000)Susan Boyle/I Dreamed A Dream: Fuck you, 2009.#2.5”), over 5,000 people were following his tweets. He had received multiple speaking invitations, inspired an homage Twitter account, “1000TimesNo,” and was the subject of interviews or feature articles in numerous publications (“If there were a congressional medal for rock criticism, this year’s recipient would be Christopher R. Weingarten,” wrote Toronto’s Eye Weekly). “I did not imagine it being as big as it was,” he says. “I did not expect people to buy fucking boxes of tweets.”

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