It’s been a minute since we’ve seen the Portland that’s depicted in Waking Up From a Nap on a Long Day of Doing Nothing. Compared to the president’s incendiary descriptions or Laika’s idyllic stop-motion fantasy, the dreamy 30-minute short film paints a portrait of the Rose City that this critic has actually seen in real life.
In Waking Up, Ezra (Ben Siver) makes his way through several magical hours of afternoon, killing time before one of his paintings debuts in a group art show. The story feels nostalgic for an artist’s early career, but the portrait is far from rosy. There’s a nervousness twisted in. Ezra can’t truly enjoy these moments due to apprehension about how his piece will be received—a universal feeling that flows across makers of many forms, experienced or otherwise.
The short joins a growing catalog by writer and director Thom Hilton, who notably shot the 2024 Matinee Baby at Clinton Street Theater. Hilton has a longstanding relationship with Clinton Street as a host of its Rocky Horror Picture Show screenings. You’ll see the theater used as a location again in Waking Up, but Hilton isn’t focusing on the moviehouse this time around. He describes his newest flick as “modeled after Portland’s 40-year tradition, First Thursday.”
“It’s not a documentary exploring the ins and outs of how the event is run,” Hilton said. “But it’s… like Halloween or Friday the 13th or any other movie that’s about a specific day. The characters and events live within that day.”
First Thursday isn’t specific to Portland; we took the idea from Seattle, as have many other cities. It’s a smart concept: downtown galleries launch new shows on the same day, drawing art lovers to multiple nearby openings.
However, the fog-filled cave that Ezra ends up in hardly reflects a typical downtown gallery’s bright halls. Instead, it’s as if he ended up at Northeast Alberta’s Last Thursday, where a group show in a dark bar is common. It’s even more likely that the looming faces criticizing him are largely in Ezra’s mind, as his anxiety paints the room chiaroscuro.
Hilton deserves credit for this character, who is played stoically by Siver. There’s something very honest about the way Ezra follows his friend Anya (Katie J. Kell) through one carefree activity after another without shaking his pensive stride. And that psychological funk will feel relatable to anyone who’s spent a whole day worrying, despite the best efforts of loved ones.
The hours still contain levity—skateboarding on side streets and a park’s cement pipe (full disclosure: Mercury managing editor Katherine Chew Hamilton appears around 10-and-a-half-minute mark, reading a book on the bowl’s edge), thrifting vintage finds while surreptitiously eavesdropping on another customer’s rant.
It’s a particular delight to barely recognize comedian, playwright, and Mercury horoscope columnist Anthony Hudson in the role of the aforementioned ranter, local crank Sir William. Hudson embodies a flavor of our city so rarely captured: a long-winded Portlander with a particular interest. At first glance, Sir William comes off as crazed, but he might also just really care about putting new snaps on his jacket.
A scene of dominant service staff ordering customers around was very funny (and so true!), but edited well for brevity—keeping the bit out of Portlandia territory. Hilton himself appears in the scene as Bud, one half of a wry day-to-night barista-to-barkeep duo, a nod to the multi-job hustleship of Portland creatives. Bud’s coworker Sigrid (Brooke Bannister) explains as much with a heavy deadpan, when asked if the pair also worked that morning: “That was in day; at night we work here.”
As funny as the short can be, it also lands its emotional notes. Ezra remains preoccupied, but manages to relax into phone calls from a confused Grandpa Jim (Jim Browning)—calls that were actually voiced by Hilton’s own grandfather who died in January 2026.
“Jim’s role was recorded in his nursing home in Beaverton,” Hilton explained. “He was able to watch an assembly of the final phone call scene before he passed.”
Much like its wandering duo, Waking Up covers a lot of ground in its short span. We cantankerously object to the idea that it’s about First Thursday, but admire such an elevator pitch.
That’s a lot more likely to make people see your film than what we would call it, which is a beautiful portrait of an often misunderstood time in your life and a story that wrestles with ambition, grief, and the ongoing pursuit of trying to relax into life as it comes.
Waking Up From a Nap On a Long Day of Doing Nothing screens at Movie Madness, 4320 SE Belmont, Fri July 3, 6 pm, 7 pm, and 8 pm, $10, tickets here
