OSA opened in 2002 with a curriculum that integrated college preparatory academics with conservatory-style arts training.

[1] It is a member of the Arts Schools Network and the National Association for College Admission Counseling.

In September 2002, OSA opened its doors with a ninth-grade class and added another high school grade each subsequent year.

[citation needed] High-school graduation and college enrollment rates continue to rank very high among San Francisco Bay Area public schools (e.g., nearly 100 percent of seniors graduated and 95 percent enrolled in college in 2013).

[5][6] In April 2014, OSA became the Master Tenant of the historic Sweet's Ballroom[7] at 1933 Broadway, which serves as a performance facility and classroom space.

In August 2016, OSA opened a new facility next door to Sweets in the J. J. Newberry's building at 1920 Telegraph Avenue to house the Instrumental Music department and the Production Design scene shop as well as a STEAM Lab.

[10] In the 2002–2003 school year, OSA received a score of 8 (out of 10) on the STAR (California Standardized Testing and Reporting Program) test (the highest in the school district) and in the 2003–2004 year, it received a 9, again the highest score in the district.

During its first several years, OSA suffered a high rate of faculty and student turnover among other management problems.

A large, lighted electronic billboard with rotating ads was installed at the toll plaza on the Oakland side of the Bay Bridge, with the proceeds benefiting OSA.

[12] The billboard was criticized because it was so bright that motorists complained it impaired their vision at night, and some residents around the bay objected to its high visibility even from San Francisco and Marin.