By Lonna Whiting
TAP Communications

Road Trip in Film and Literature: A List

“The Grapes of Wrath,” by John Steinbeck

“The Hitchhiker’s Guide to the Galaxy,” by Douglas Adams

“Zen and the Art of Motorcycle Maintenance,” by Robert Pirsig

“Blue Highways,” by William Least Heat-Moon

“On the Road,” by Jack Keroac

“Thelma and Louise”

“Little Miss Sunshine”

“The Trip”

While hitchhiking and heading down the highway are common American film and literature motifs, local filmmaker and TAP grantee Oscar De Leon and his partner at Chamber Six Media, Kevin Ackley, weren’t afraid to hit the road and get their own unique take on the subject matter — a musically and visually psychedelic trip to the Southwest inspired by the music of local hip-hop artist Huck.

Filmed across the American Southwest, “Trip 27” unfolds over five chapters – each a music video from local musician Huck.’s first full-length LP of the same name – on a psychedelic hitchhiking road trip. 

Stylistically and narratively sprawling, the 25-minute film weaves through various genres and styles to tell one story – written and directed by De Leon (under artist name “guero”).

Huck., or Jared Huckell is a notoriously under-the-radar musical talent who released his first two self-produced albums in 2018 at the age of 25 and has since produced several others, releasing the LP “Trip 27” on Thursday, just ahead of the film release party. 

De Leon is a grantee of TAP’s Individual Arts Partnership Grant program, which helped support the project that took about a year and a half.

The idea

For De Leon and the film’s editor Kevin Ackley, the idea for “Trip 27” began with Huck.’s work and evolved to include elements of road trip narrative, modern musical theatre, Joseph Campbell’s conceit of the hero’s journey, and the literal fact that turning 27 as a milestone of young-ish adulthood. 


“Huck. would tell you that one of his interpretations of that title is that it’s his 27th trip around the world,” De Leon said. “And so it was that the title itself was sort of the launch point for so many ideas. We knew, based on the first song on his album, which is titled ‘Arizona,’ it just had to end up there. That’s when we knew it had to be a road film.”


Ackley, who delved into the painstaking work of editing a year’s worth of production, as well as a week’s worth of road-trip content down to about 25 minutes on screen, interprets the work as being a metaphor for the creative process itself.


“Sometimes we ask ourselves why do we keep creating in the face of defeats?” he said. “But not giving into that is the only thing that sometimes continues our propulsion forward.”


De Leon echoes that sentiment. “There’s one song called ‘Meadow,’ where Huck. gets into a lot of his familial dynamics and his mental states,” he said. “A lot of ‘Trip 27’ the album is based around his yearning for, you know, creative desire and stuff, like where you get stunted as a creative.”


The execution

About halfway through the pandemic, De Leon and team decided to take the show on the road and explore the American Southwest as a backdrop for the film itself that was also noted heavily in Huck.’s LP.


“I’ve been so enamored with classic American road films and that was just sort of the base of everything, De Leon said. “I spent a lot of time listening to the album and formulating the pictures that were in my head. From there we just kind of ran with it.”


Ackley said the crew of six had to coordinate schedules during the pandemic to make everything work out and ensure the actual road trip itself could go on safely without a hitch.


“The film started in March 2020 and filming two times every month, so it was like two days or a weekend, and then the road trip in May, and then whenever we could fit in,” he said. “By the time we finished the road trip, we had 95% of the film done.” 


The final product

Chamber Six Media hosted a release party at the Fargo Theatre on Saturday, August 28, an event De Leon hoped set the scene for the community to witness the collaboration in real life.


“Trip 27 the film is a multilevel experience,” De Leon said. “It has to be a shared experience in a theatre, so we are all falling for the illusion of a different world collectively.”

About the Author

Lonna Whiting is a growth strategy and communications consultant and owner of She holds an MFA in Creative Writing from Minnesota State University Moorhead and frequently collaborates with all types of clients, ranging from startups to arts organizations like The Arts Partnership. 

Whiting is currently working on a nonfiction book about Alzheimer’s Disease and its future impacts through the lens of her own experience with a mother diagnosed at age 61.


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TAP grantee Oscar De Leon, Huck. partner on road trip film, “Trip 27”

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