First recorded (as “Leilani”) by Sol Ho’opi’i & His Novelty Quartet (1935).
Hit version by Bing Crosby (US #1 1937).
Also recorded by Harry Owens & His Royal Hawaiians (1938), Andy Williams (1959), Sam Cooke (1960).
From the wiki: “Harry Owens wrote the song in 1934 for his just-born daughter, Leilani. The name has a figurative meaning: Small Hawaiian children were carried on their parents’ shoulders like a lei (garland), so the name took on the meaning ‘heavenly child’.
“‘Leilani’ was first recorded in Hawaii by Sol Ho’opi’i & His Novelty Quartet in 1935, as the B-side of the Brunswick Records’ 78-rpm ‘Hawaiian Honeymoon’. The song was famously featured in the 1937 motion picture, Waikiki Wedding, for which its Bing Crosby recording won the Academy Award for Best Original Song with Crosby’s recording going on to become one of the top hits of 1937. The song made another film appearance in the 1938 comedy Cocoanut Grove (set in Los Angeles; not Hawaii), starring Fred MacMurray, performed by the song’s composer Harry Owens & His Royal Hawaiians.
“‘Leilani has since become a standard of popular and Hawaiian music, easy listening, and to some extent jazz; and has occasionally been performed by both country and rock music artists. It was recorded several times in the late ’50s when Hawaii became the 50th US state. Andy Williams released the song twice – first, in May 1959, on the album Two Time Winners (on which also appeared the hit single ‘Hawaiian Wedding Song’); and again in September 1959 for the thematic album To You Sweetheart, Aloha (reissued in 1965 as The Hawaiian Wedding Song) for which he re-recorded ‘Sweet Leilani’.
“Sam Cooke recorded ‘Sweet Leilani’ in 1960 for his album Cooke’s Tour, his first for RCA Records and designed as a ‘adventurous travelogue exploring various territories around the world.'”
Bing Crosby, “Sweet Leilani” (1937):
Harry Owens & His Royal Hawaiians (1938):
Andy Williams, “Sweet Leilani” re-recorded version (1959):
Sam Cooke, “Sweet Leilani” (1960):