Kalama was born on June 29, 1916. He was born on the Big Island of Hawai'i. At Kalakaua Intermediate School in 1931, Benny began playing trombone in the band. Upon graduation from
McKinley High School where he played in the band, Kalama hooked up with Leonard "Red" Hawk and the Waikikians. Kalama's ability to read music, rather than play by ear, got him hired by the more successful bands. It was Hawk who wrote the lyrics and music to the ubiquitous song
May Day is Lei Day in Hawaii. In 1938, Kalama played steel guitar substituting for Sam Kaʻapuni with the Malcolm Beelby Orchestra. Kalama worked with the Don McDiarmid Sr band at the Royal Hawaiian Hotel, the Kewalo Inn and La Hula Rhumba on Lulalilo Street. McDiarmid, along with
Johnny Noble, had penned Hilo Hattie's signature tune
When Hilo Hattie Does the Hilo Hop. During this period of his career, Kalama worked with Alfred Apaka, George Kainapau, Alvin Isaacs Sr and
Tommy Castro. In between his participation with the McDiarmid band, Benny played with the Wally Lavque's band the years 1952–1955 at the
Moana Hotel in Waikiki. In 1955, he began working with Alfred Apaka in Las Vegas, followed by 15 years with Henry Kaiser's
Hawaiian Village. Kalama's arrangements are credited with helping Apaka's success. On radio, Kalama was a director and arranger on KGU's
Voice of Hawaii Hawaiʻi Calls. ==Later years==