The idea of a museum to highlight the history of Hollywood High School , as well as the famous alumni who attended HHS, was spearheaded by Jeanne Hon, principal of HHS from 1991 through 1997. Jeanne would go through the basements and storage area of HHS, looking for space to be converted into offices and instructional facilities. During her searches, Jeanne found a great deal of HHS memorabilia stored in boxes that had been largely forgotten. In 1991, Jeanne appointed Jerry Massey, then the Assistant Principal for Counseling Services, to supervise a project to create space to publicly display memorabilia that would depict the history of accomplished individuals who attended Hollywood High School.

In the fall of 1991, Jerry Massey and Hub Braden, a production designer for Universal Studios, embarked on a two-year project of creating the Hollywood High School Museum. The Library building, which was built in 1910 and served as the first auditorium for the school, was designated as the location for the HHS Museum project. Walls were patched and painted. Walnut paneling and trim, which has been painted over, was stripped and returned to the original style and look. Thematically correct crimson-colored carpet was installed and HHS-authentic branding and archival photography was applied to throughout the interior. In addition to the foyer, rooms 501 and 502 were added as galleries to the museum by the spring of 1993, along with the Library balcony (which also carries the HHS tribute exhibition for HHS alumni who are fallen heroes in U.S. armed conflicts overseas). L.A. Mayor Tom Bradley assisted in the dedication and opening of the HHS Museum in March 1993, an event attended by several hundred people. Jerry Massey continued to expand the collection of the HHS Museum to include memorabilia that extended beyond entertainment industry related alumni. Notable alumni from the political, scientific, arts and philanthropic sectors also came to be celebrated in the Museum.

In 1997, Hollywood High School alumnist and Assistant Principal Dick Rippey assumed the management of the Museum, adding new displays to the collection. His substantial contributions culminated in 2002, when Dick retired from the L.A. Unified School District. Celebrity alumnist and HHS Alumni Association Vice President Carole Wells has continued to manage the Museum to present day. Carole is working on a variety of initiatives, including online access to the museum collection and scheduling special tours of the museum to visitors from around the world.