Henry K. Kailimai Sr. (1882 – February 7, 1948) was a prominent Hawaiian musician, composer, and bandleader known for his significant contributions to popularizing Hawaiian music in the mainland United States. Born on the island of Oahu, Hawaii, Kailimai was a talented multi-instrumentalist, proficient in playing the ukulele, guitar, and mandolin. He was a protégé of the renowned ukulele virtuoso Ernest Kaʻai and served as an organist at his Mormon church.

Kailimai gained widespread recognition when his band, the Hawaiian Quintet, performed at the Panama–Pacific International Exposition in San Francisco in 1915. The group's daily performances, surrounded by tropical plants, captivated fairgoers with their rendition of "On the Beach at Waikiki," which became one of the first Hawaiian songs to achieve commercial success on the mainland.

The exposition also caught the attention of industrialist Henry Ford, who was so impressed by Kailimai's music that he invited the band to Detroit to become the official musicians for the Ford Motor Company. Known as the Ford Hawaiians, the group became a popular attraction in the Midwest, performing at Ford events and on the company's radio station.

Kailimai moved to Detroit to fulfill his role with Ford, where he lived until his death in 1948. His legacy includes not only his famous composition "On the Beach at Waikiki" but also other songs like "Sweet Brown Maid of Kaimuki" and "Paradise Isle," which contributed to the spread of Hawaiian music in the early 20th century.