It is named after a former math and computing teacher Archie Williams, who was also a gold medalist in the 1936 Summer Olympics, a flight instructor with the Tuskegee Airmen, and one of the first African-American meteorologists.

[4] In 1958, Redwood High School opened to accommodate students from Corte Madera, Larkspur, Kentfield, Ross, and Greenbrae.

[8] During the protests against police brutality and racism that followed the murder of George Floyd, school officials initiated a process to consider changing the name of Sir Francis Drake High School, citing "the racist and violent acts of Francis Drake, a slave trader, slave owner, and colonizer, and the legacy of white supremacy he represents," and noting that "honoring such a person is counter to the values held by our community and counter to the lessons and values we wish our students and colleagues to learn.

The 1986-87 edition was a winner of Columbia University’s Silver Crown Award for high school newspapers in 1988.

[21] The Jolly Roger has been a regular recipient of the Medalist rating, given to the top 5% among high school newspapers in its class in United States.

[22] The school's NICA NorCal League mountain bike team is notable for being one of the first in the nation and has won numerous regional and statewide competitions.