The film was shot entirely on location in Koganecho, an area of Yokohama which has been spared urban development and still holds an atmosphere redolent of the 50's. The theater which Maiku Hama uses for an office and the buildings which are shown in the film are still in actual use. The vintage car "Met's Metropolitan 1954" which Maiku uses as his car in the film is actually owned by Kaizo Hayashi. The result is a pastiche reminiscent of the golden era of 1950's film, an effect which is heightened by the director's decision to film in monochrome. The Most Terrible Time in My Life is the first in a series of three Maiku Hama Private Eyes films. The other two installments have been released in Japan, and have also premiered at the San Francisco International Film Festival.