If it pains you to see flesh-and-blood contact disappearing in a digital world, you might relate to Smigly, an average guy in search of love. Dumped by corporate America, he sits on the landing of his apartment, blowing his saxophone while a neighbor jeers: “You know the tune, ‘Go Get Lost’?” He chokes on a nut, and his girlfriend won't look up from her laptop. He becomes a ventriloquist, and gets laughs only when the dummy pees on him. The irony of his quest for human feeling is that he too is unreal; he's just a figure on a computer screen.

Smigly is a rising YouTube cartoon series with an emotional theme: How do you survive today’s onslaught of rejection while keeping your soul intact? The show’s creator, Allen Mezquida, knows that struggle. When his career as a jazz saxophonist floundered in the late '90s, Mezquida took up animating and entered the movie business, which repelled him. Now he funnels his conflicts into Smigly. To Don Barrozo, a trumpeter who has edited The Simpsons since its inception, Mezquida’s funny-sad nebbish is the Charlie Chaplin of the cartoon world; his walk alone, says Barrozo, “tells you all you need to know about Smigly's state of mind, be it dejection or elation.”

In its twenty months online, the show has amassed about 100,000 hits—“which for a one-man band is pretty good,” declares Mezquida. When he isn’t busy animating Smigly, Mezquida spends much of his life trying to conquer one of today’s great business conundrums: how free Internet content can generate an adequate income. Smigly still isn’t making him one, but “ways of making money are coming,” he says.

Mezquida’s own story has a theme that’s weighing heavily on artists these days: the need to reinvent oneself in a digital age, or risk disappearing. When I first encountered him in 1996, he was in New York, playing cool jazz with all the heart of his animated alter-ego. He performed with giants—Gerry Mulligan, Art Blakey, Mark Murphy—but his one solo CD, A Good Thing, barely caused a ripple. Soon he joined a legion of talented New York jazzmen who were losing the fight against obscurity. “I was feeling underappreciated, a lot of self-pity,” he says. “I felt like, I’m not reaching people with my music because they’re just not interested. I was questioning the pertinence of jazz now. I thought, I have to do something creative, but is it gonna be jazz?”

He turned to his side talent—illustration—and detoured into magazine work. Then he taught himself flash animation. Working in advertising during the dot-com windfall, he earned enough of a killing to take a year off. During that time, he says, he “made a short cartoon about a really bitter saxophonist.” The video helped land him a job in Los Angeles as a production animator for big-time movies, including Aladdin and Toy Story. The work paid handsomely—“but I was just holding an oar in the bowels of a Viking ship. And executing the ideas of morons that I didn’t respect. The kind of cartoons I liked had a great vibe—some kind of intelligent message, without being on a soapbox.”

Last year, in his free time, he began producing Smigly. The segments—seventeen so far—are each less than three minutes long, ideal for an ADD-ridden culture. But as the sole animator, Mezquida labors over each episode for hundreds of hours. Much of that time is spent perfecting Smigly’s facial expressions and body language until the little figure achieves a lifelike pathos.

VIDEO: Click here to watch an average day with Smigly.

Where to put his series was a dilemma. Having done “soul-crushing” network pitches for previous cartoons, he wasn’t eager to throw Smigly, or himself, to the wolves. At the same time, he rebelled against turning to YouTube: “I was still very old school—‘I’m not gonna give this away!’ Then he realized that YouTube might give him a platform “to put jazz back into my life and get it out there in a way that could reach people.” The amusingly dippy soundtrack music is by jazz bassist Joey Altruda (the voice of Smigly), but that’s Allen on sax—notably in I Heart Jazz, in which Smigly plays his heart out, literally:

Signs of hope keep appearing. The BBC broadcast the episode Shitcanned. (They aired it as Sacked to protect the faint of heart.) Recently Mezquida was approved to become one of about 10,000 YouTube “partners,” whose content holds enough commercial promise to make it attractive to advertisers. Google AdSense matches up ads to the chosen sites, and partners earn about $2 per thousand site hits. Unless the views run in the millions, however, you can forget any fantasies about living off the profits. Stronger earning potential exists in licensing out one’s videos or marketing tie-in merchandise. Mezquida is now offering Smigly T-shirts and mugs that read F**K MARKETING.

In the meantime, a guy’s gotta eat. These days he’s part of a band that accompanies Molly Ringwald in her own metamorphosis from underemployed actress to jazz singer. He also plays in a group called Cow Bop, billed as “The Best in Cowboy Jazz” by its founder, guitarist Bruce Forman.

Wouldn’t Mezquida be thrilled if a network swept him off to TV land by offering a juicy production deal? “I wouldn’t say I’m drooling for it,” he responds. “I’m more excited about this new digital world online, and in growing a fan base that will allow me to keep Smigly the way it is. If you have a lot of views you can get sponsorship, too. You know—‘Lexus Presents Smigly.’”

Conventional television, he claims, isn’t long for this world anyway: “Soon the mainstream will be viewing the Internet on their TV screens. It’s already happening—there’ll be one entertainment center where people watch TV and Internet and movies. Most people are paying these huge cable bills for 10 channels that they want among 200 that are garbage.”

Meanwhile he intends to keep reminding us, through his cartoon muse, that we’re not as powerless as we may currently think. “Even a little dog can piss on a big building,” he says. “The gatekeepers aren’t the only ones holding the keys to the kingdom anymore. And they’re afraid.”

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James Gavin is the author of Deep in a Dream: The Long Night of Chet Baker and Intimate Nights: The Golden Age of New York Cabaret. His work has appeared in The New York Times, Vanity Fair, and Time Out New York, among other publications. He lives in New York City.