The school avoided destruction when on March 4, 1942, the Imperial Japanese Navy attempted to bomb Pearl Harbor a second time.

Roosevelt High School is most famous for its buildings and landmark domed bell tower constructed in Spanish mission architectural style, currently being restored through grants of the Hawaiʻi State Legislature.

Adjacent to the historic bell-towered building is the 2001 Hawaiian basalt sculpture "Hoʻokahi" (To Make as One), by Mark Watson.

In January 2014, a police officer shot a knife-wielding runaway teen who was being detained for trespassing and became disruptive at the school.

It is situated in Makiki's Kalāwahine Valley adjacent to the National Memorial Cemetery of the Pacific overlooking downtown Honolulu and Ala Moana.