In Kyle Eaton's debut, Shut Up Anthony, the filmmaker skewers Portland "fun" with a scene at a work party for a hip creative agency. In an exposed-brick bar decked with Christmas lights, the film's protagonist, Anthony (Robert D'Esposito), tensely navigates his way through throngs of cool professionals. A woman with frizzy hair introduces Anthony to her boyfriend, who has an enormous, Amish-style beard and a cutely manicured haircut. A man with swooping hair, a bolo tie and a (differently) bushy beard talks to an HR guy who promises to look the other way if he has "a few too many drinks." A pudgy dude with a beard and snapback gives Anthony mushrooms, and he nervously joins in a bird-flipping group photo that a workmate wants to send to his girlfriend Samantha (Katie Michels), with whom he's just had a serious argument.

It's a nerve-wracking social trial swaddled in a pastiche of hipness that culminates with Anthony's abrupt firing for "substandard work performance and unsatisfactory work quality" the next day. When Anthony gets a text from Samantha informing him she wants a break, he decides to head to a rarely used family timeshare. There, he reconnects with his old friend Tim (Jon Titterington), an academic who is hiding out from his domineering family, drinking heavily and reconsidering his marriage.

The film, which screens as part of the Northwest Film Center's Northwest Tracking series on Thursday, isn't alone in speaking to the dissatisfaction many creatives feel in artist-friendly Portland. Alongside films like Matt McCormick's Some Days Are Better Than Others (2010) and Macon Blair's Sundance Grand Jury Prize-winning I Don't Feel at Home in This World Anymore, Eaton's Shut Up Anthony is part of a new wave of Portland indies that tackle what it's like to feel like an outsider in the city where outsiders are supposed to fit in.

The protagonists in these films are similar to Anthony, caught in the early-30s penumbra between the end of youth and the beginning of middle age—they aren't quite "old," but they're past the age where youthful indiscretions are cute. These characters aren't secure in their careers—I Don't Feel and Some Days revolve around characters with little money—and they certainly aren't secure in their relationships. As Anthony, D'Esposito is a twitching mess of guilt-ridden nerves who's unable to emotionally commit to his loving girlfriend and belittles her to Tim, who manifests his neuroses about his marriage by micromanaging coaster usage and hot tub rules. Anthony is a grounded answer to a wacky stoner from a Judd Apatow movie, except his childish antics are met with annoyed silence.

These characters should be right at home in Portland, the city where, as the story should go, Peter Pan Syndrome is a lifestyle. But, for these characters, the city just isn't panning out.

Although alienation and ennui are universal, these films speak specifically to the ways in which Portland can be a huge bummer. Though they differ in tone and content, they all portray the city as a place whose hostility is masked by urbanity. These are visions of Portland where the cute apartment and trendy bar become psychic prisons. Anthony reminded me of a friend of mine, while Some Days gets at how smothering the cutesiness of this city feels when you're out of work. And sometimes, you just don't want to be bothered by one of those charity assholes who try to wave you down as you try to walk through downtown.

SEE IT: Shut Up Anthony screens 7 pm, Thursday, June 29 at NW Film Center's Whitsell Auditorium. Director Kyle Eaton will introduce the film. I Don't Feel at Home in This World Anymore streams on Netflix. Some Days Are Better Than Others streams on Amazon Video.