"PORTLAND ISN'T THE SAME as it used to be," bemoans poet Walt Curtis in Penny Allen's 1978 directorial debut Property. It's one of many gripes in the film that could be lifted straight from Portland today: artists don't make enough money, the neighborhood's changing, the landlord raised the rent.

Property gave Gus Van Sant his first film credit, as a "sound recordist," and it prominently features renowned Portland poet Curtis, who plays a (fictionalized?) version of himself. (Eight years later, Van Sant would use Curtis' novel Mala Noche as the basis for his first feature film.) Based on Portland-bred Allen's experiences in the Lair Hill neighborhood in the 1970s, Property recasts artists and prostitutes and drug addicts as a sort of wacky neighborhood association. As the characters carouse at bars, smoke pot in sagging Victorians, and conspire to save their homes from a developer, the film offers a priceless snapshot of what Portland looked liked before you moved here. (Hate to break it to you, but it was weirder then.)

Allen's 1981 follow-up, Paydirt, is a similarly fascinating snapshot of Oregon's past: With a cast that features many of the same actors as Property, Allen tells the story of a woman trying to run a vineyard on land originally settled by her great-grandfather. When grapes can't pay the bills, she turns to growing marijuana—attracting the attention of a band of thugs bent on stealing their weed. (Sample dialogue: "What else do you do besides rob people?" "Play music.")

Allen's first two films are most noteworthy for the era they capture, and they're screening back-to-back at the Hollywood on Saturday, April 26, with Curtis, Van Sant, and Allen herself on hand for a Q&A. Her more recent work, screening Sunday, April 27, is documentary in nature: The Soldier's Tale is about the Iraq War, inspired by a veteran she met on an airplane; Late for My Mother's Funeral is about a French Algerian Moroccan man who is... late for his mother's funeral. These don't have the local appeal of Paydirt and Property, but they're nonetheless relevant to the evolution of a fascinating and lesser-known Portland filmmaker.