Two years ago, BuzzFeed ran a piece called “62 People Who Dressed As Matt Bellassai for Halloween.” It was photo after photo of people in plaid shirts and black eyeglasses holding wine glasses, or with a partner dressed as a wine glass. BuzzFeed was Bellassai’s employer at the time, and he had made a name for himself there with his “Whine About It” segments, videos in which he would drink a bottle of wine and complain about everything from co-workers to Christmas.
“It is weird to have done something that reached the point where it’s so familiar to some people that they expect other people to see that image and understand it,” says the 27-year-old comic, speaking by phone from a tour stop in Atlanta.
When he was a student at Northwestern University, he thought he’d wind up writing about news and current events for a magazine like Time or Newsweek. Instead, he’s made a career out of complaining: He has a new book of personal essays called “Everything Is Awful,” a podcast he launched in August called “Unhappy Hour,” and a popular series of videos called “To Be Honest.” His second tour doing stand-up in larger clubs and theaters wraps up Sunday with two shows at the Wilbur Theatre.
A college internship at the Chicago-based magazine In These Times showed Bellassai that he wasn’t as passionate about the news as his colleagues. When he graduated, he applied to BuzzFeed thinking he could still write about the news but in a more lighthearted way. After writing humorous lists and captions for animal videos, he struck gold with the “Whine About It” series. “I was like, well what if I drank a bottle of wine and complained, and you could film it?” he says.
A career was born. The videos were a hit, some getting over a million views on YouTube. People liked to see Bellassai get tipsy — he was actually drinking wine in the videos — and increasingly cranky on camera. In one popular episode, he took aim at autumn and all things pumpkin spice, saying “pumpkin tastes like if you put cinnamon on a sand castle.”
Instead of slogging through open mics and clubs, the traditional path for stand-up comedians, Bellassai made a name for himself on the Internet. Some comics who have taken the traditional route look down on what they call “Internet comedians,” but Bellassai doesn’t see a huge difference between them. “I think people consider it an easier path. But it takes a lot of work to build an audience and to keep them happy and to keep them coming back,” he says.
He has found there are aspects of playing to an audience that a comic can only learn by performing live, but he was able to shape his voice and get feedback by experimenting online. “When you go to an open mic night, a lot of it is about collecting data,” he says. “You’re figuring out: OK, this joke, people respond to it, this one they don’t. That’s the same way that people interact with you if you’re posting a video. Some videos do a lot better than others, some do a lot worse.”
Since he left BuzzFeed in January 2016, he’s faced a new challenge — building an audience on his own without the backing of a giant media company. Diversifying has helped. He has spread his voice to new audiences in publishing and podcasting, and says his “To Be Honest” videos are starting to get the same numbers he had at BuzzFeed.
“It’s a little harder to be experimental when it’s just you, and you sort of need to count on a certain number of successes to keep the machine going,” he says. “I’ve been fortunate that I’ve had, now, a couple of years on my own and it’s gone pretty well and I get to keep doing it.”
It’s also tough being his own boss. “I would never trust me with anybody else. And now I’m my own boss, and it’s hard to keep myself motivated and get up in the morning and not take a nap and watch Netflix all day.”
One problem he doesn’t have is finding new things that irritate him. “Living in New York, I could walk outside, walk one block, and have a list of 100 things that piss me off,” he says. The big difference is that his grievances have gotten more specific. “The early videos were kind of broad categories like kids and weddings, and now it’s like, ‘The worst part about being a bridesmaid at the third wedding you’ve ever been to in your 20s . . .’ That video might be coming soon. We’ll see.”
At the Wilbur Theatre, Dec. 10 at 4 and 8 p.m. Tickets: $42, 617-248-9700, www.thewilbur.comNick A. Zaino III can be reached at firstname.lastname@example.org.