Cinema 21 is one of the most beloved locally owned theaters in the Portland area. Built in 1925, it was initially given the name "The State Theater", where it showed second-run silent films under owner E.H. Marston. The theater was labeled as one of the "finest west side suburban theaters" by the Sunday Oregonian upon it's opening, and also featured a pipe organ for special musical performances. Some programming included classic love story “Secrets” and historical drama “The Covered Wagon”. Additionally, there were also live performances, one of which included a mind-reading “Doctor”, a common act for the time. By 1940, the theater changed ownership to Arthur A. Jones and Lewis Boyd, and was re-named "The Vista". To keep up with the rapidly evolving industry, the building was remodeled to accommodate new projection equipment and seating arrangements. In 1941, Leo Pallay took over operation, renaming the theater, "21st Avenue Cinema" until selling it in 1962. Pallay began working in cinemas in 1914 as a mechanical organ player for silent films, and eventually went on to monopolize the Portland theater industry, owning eighteen cinemas in the area.
Finally, in 1962, the theater was renamed for the last time, settling on "Cinema 21", and opening with the film "The Mark". Some programming of the era included a fair share of “adult” films, though not entirely explicit. Films shown at Cinema 21 were typically revered as cinematic achievements, exotic and artistic. From there, the theater began to build up its reputation as one of Portland's most important cinemas. In 2013, the interior was renovated to include two new screens and a concessions stand, followed by new aesthetic changes like new paint, seats, and projection equipment. As one of the city's longest lasting theaters, Cinema 21 has become a hub for films from all corners of the industry. Specializing in foreign, independent, and historical films, this theater has been an exemplary example of exhibiting films that may not be shown anywhere else. Due to this reputation, Cinema 21 has played host to multiple local films festivals, and celebrated its 100th anniversary in 2025 with a festival, and guest speaker Academy Award winning director Sean Baker.