Josh Loeb’s directorial debut, In Spite of Ourselves, follows a Portland pastry baker and a visiting Los Angeles comedian through an unexpected romance. Inspired by John Prine’s song of the same name, the film features local businesses and familiar Southeast Portland locations, including Tabor Bread, Southeast Clinton Street and Laurelhurst Park.

Key Takeaways

• Josh Loeb wrote and directed In Spite of Ourselves, his first feature film
• Conor Leslie plays Portland baker Hannah, opposite Brett Dier as visiting comedian Archie
• The characters first meet over a cinnamon roll at Tabor Bread
• Southeast Clinton Street and Laurelhurst Park appear in the film
• Portland food writer Michael Russell makes a cameo as himself

Josh Loeb Makes His Directorial Debut in Portland

Loeb wrote and directed the romantic comedy after a career in the restaurant industry. The story borrows its title and central theme from John Prine’s song, balancing the excitement of a new relationship with the complications that follow.

Southeast Portland was a deliberate choice for the setting. Loeb’s familiarity with the area grew through family visits, and he wanted its streets, businesses and autumn scenery to be part of the film rather than a generic backdrop.

A Baker and a Comedian Meet at Tabor Bread

Leslie plays Hannah, a pastry baker who meets Archie, played by Dier, when he visits Tabor Bread. A cinnamon roll sparks their introduction, and the two begin a whirlwind romance before work, distance and personal responsibilities complicate their plans.

The opening encounter places Hannah within Portland’s neighborhood bakery culture, using a real local business as the starting point for the relationship.

Hannah’s demanding career and Archie’s obligations to his family add pressure as the couple tries to move beyond their initial attraction. The film draws humor from their differences while giving both characters more serious decisions to make.

Southeast Portland Streets and Parks Appear on Screen

The couple walks along Southeast Clinton Street and spends time in Laurelhurst Park, taking their relationship beyond the bakery. Loeb also uses neighborhood restaurants and other familiar places to establish where the characters live and spend time.

Portland’s mix of urban and natural filming locations gives filmmakers a range of settings, but In Spite of Ourselves focuses closely on Southeast Portland.

Rather than moving between unrelated landmarks, the film follows the characters through a connected set of neighborhood spaces, from indoor food businesses to residential streets and parkland.

Restaurant Experience Informs the Film

Before turning to filmmaking, Loeb founded the Santa Monica restaurant Rustic Canyon and spent decades working in hospitality. He has compared directing a film with running restaurants, noting the coordination needed to bring together creative teams.

That experience also informed Hannah’s character. Loeb has spoken about his familiarity with bakers and the demands of their work. Food writer Michael Russell appears as himself, adding a recognizable figure from Portland’s restaurant community to the cast.

Portland Screenings Continue Through October 15

In Spite of Ourselves opened in Portland on October 9 at Living Room Theaters, 341 SW 10th Avenue. Screenings are listed through Thursday, October 15, with reported ticket prices of $6 to $11 and showtimes varying by day.

The Portland engagement follows an October 2 opening in New York. A Los Angeles run is scheduled to begin October 16 at the Landmark Nuart Theatre.

Frequently Asked Questions

What is In Spite of Ourselves about?

The romantic comedy follows Hannah, a Portland pastry baker, and Archie, a visiting Los Angeles comedian, as they navigate a relationship complicated by distance and personal responsibilities.

Who directed In Spite of Ourselves?

Josh Loeb wrote and directed the film, his feature directorial debut. It draws inspiration from John Prine’s song of the same name.

Who stars in In Spite of Ourselves?

Conor Leslie plays Hannah, and Brett Dier plays Archie. Portland food writer Michael Russell also appears as himself.

Which Portland locations appear in the film?

The film features Tabor Bread, Southeast Clinton Street and Laurelhurst Park, along with other Southeast Portland locations.

Where can audiences watch the film in Portland?

The film is scheduled at Living Room Theaters, 341 SW 10th Avenue, through October 15, 2026. Showtimes and ticket availability vary.