Comedian Matt Oswalt describes his brand of humor as "very dark and painful and self-deprecating and suicidal and sad and depressing. It’s just a big goop of sadness."
In other words, the kind of material that’s well-suited for uber-indie comedy festivals or late-late-late night routines at grungy, basement clubs in the Valley. Or, as it turns out, YouTube.
For the last two years Oswalt has defied the notion that YouTube is mainly a haven for Beliebers looking for nail art tips or teen boys in search of video game-style fantasy sequences, by accruing a devout, comedy nerd following around his off-beat comedy series Puddin.' Amongst the shows fans—and guest stars—are Robin Williams, Christopher Guest mockumentary regular Michael McKean, David Koechner, "Weird Al" Yankovic; Conan O’Brien sidekick Andy Richter; and Patton Oswalt, who’s Matt’s older brother.
"People describe it as a comic’s comic show," says Oswalt. "Which means very low views, low hits, but a cultish following."
It also means, Oswalt jokes, "poverty." Unlike those Belieber-beloved YouTube sites, Oswalt says Puddin’ brings in "a couple hundred bucks a month" from ad revenue.
Still, his following is hardly meager. Some Puddin' episodes have gotten hundreds of thousands of views, and the series overall has received close to 3 million hits and has about 9,000 subscribers.
The premise of the show is simple: Each 30 second strip takes place in an office kitchen, where Oswalt—dressed in an Office Space uniform of drab dress shirt and cheap tie—is silently trying to eat a cup of pudding. His peace is inevitably disturbed by Eddie Pepitone, the series’ star, a boorish loud-mouth who erupts into off-color rants involving everything from Taylor Swift to Japanese internment camps. Through it all, Oswalt never utters a word, but continues to slowly spoon his packaged dessert. His performance is all pained, put-upon slow burn.
Oswalt says the inspiration for Puddin’ came from his own experience as a temp worker back in high school and college.
"When you do temp work, you’re always working in new companies and you’re always the new guy, and people are kind of curious about you. I got bored just talking about myself all the time, so I’d make up these stupid things—like, I’d be in the office kitchen and instead of telling people where I was from, I’d make up asinine things about myself just to amuse myself.
"Years later, when I was kicking around ideas, I liked the idea of having this office kitchen set-up and I thought Eddie Pepitone would be the perfect vehicle."
The larger-than-life Pepitone, in fact, is so crucial to the series’ tone, that Oswalt said had he turned the role down, there wouldn’t be a Puddin.' "He’s the only person who could have possibly pulled this off."
But as for the actual writing—despite the loose, improv-y feel, each episode is scripted—that’s handled by Oswalt, who dutifully writes two episodes a day, in between writing screenplays.
"I think there are a lot of situations that lend themselves to these," he says. "Sometimes I’ll write something on Twitter and think, ‘That’d be a good Puddin.’ Or I’ll be at Starbucks and overhear some crazy, homeless man behind me in line and I’ll say, ‘That was pretty funny, I’ll steal what he said.’ I don’t have a process. But I try to do two a day. I like writing seven days a week. I’m pretty good at that."
Filming takes place once a month, when Oswalt, Pepitone and various guest stars congregate in the kitchen of Patton Oswalt’s management company ("it’s free") and shoot from 8 p.m. to however long it takes to shoot a month’s worth of shows. (Puddin’ airs Monday through Friday, though there was a summer hiatus when the management company moved.)
One of the most memorable nights was when the group—including Colin Hanks, Koechner, "Weird Al," and Patton Oswalt—filmed the Puddin’ Christmas special, a nearly three-minute long, black-and-white riff on It’s a Wonderful Life, only with a decidedly dark and un-feel-good take.
"We were riffing and goofing around, that was a lot of fun," says Oswalt. "That was our highest-level production level of Puddin’."
Although the series is not making Oswalt rich, he says YouTube is a helpful platform when it comes to trying to pitch networks (he’s discussed turning Puddin’ into a half-hour TV series, but as of yet there’s no deal).
"It definitely makes it easier when you’re in a room with people who have actually seen it," he says. "Let’s face it. L.A. is an illiterate town. People don’t read, they watch things. So when people have actually seen your stuff and they get an idea of who Eddie actually is; of the darkness of the tone you’re going for—I mean, that’s a really hard thing to show on paper."
The Internet also offers comedians the freedom to be far more quirky and sinister than they’d ever get to be on television.
"The thing about working for YouTube is you don’t have to answer to anybody," says Oswalt. "You get to do what you want to do. There’s some stuff that I’ve put up that’s really offensive, but hey, you move on the next day. And some stuff has been absolutely clunky and un-funny and terrible, and the next day you redeem yourself."
As to how he maintains his straight face throughout Pepitone’s rants, he says, "It’s really difficult."
"What I’ll do is I’ll look down at my arm and I’ll count the hairs on the back of my arm. That’s really a trick I’ve learned. There have been times where we’re literally on the eighth or ninth take and I’m still cracking up. It’s so off the wall. So I just focus on counting hairs."