My Boy Lollipop

First recorded (as “My Boy Lollypop”) by Barbie Gaye (1956).
Hit version by Millie Small (US #2/UK #2/IRE #1 1964).

From the wiki: “‘My Boy Lollipop’ (originally written as ‘My Girl Lollypop’) was written in the mid-1950s by Robert Spencer of the doo-wop group The Cadillacs, and is usually credited to Spencer, Morris Levy, and Johnny Roberts. It was first recorded in New York in 1956 by Barbie Gaye. A cover version, recorded eight years later by Jamaican teenager Millie Small, with very similar rhythm, became one of the top-selling ska songs of all time.

“When it came time to record, in 1956, Gaye cut school and took the subway to a recording studio in Midtown Manhattan. The song was released as a single by Darl Records in late 1956. It was heavily played by New York radio DJ Alan Freed, and listener requests made the song #25 on Alan Freed’s Top 25 on WINS, New York in November 1956. (Ellie Greenwich, then a teenager living on Long Island, and before becoming a hit songwriter, was so taken by the record that she named herself Ellie Gaye when she embarked on her recording career.) However, Gaye’s recording of ‘My Boy Lollypop’ failed to make an impression in other markets and it did not chart nationally. Consequently, the song remained obscure outside New York City.

“Eight years later the song was discovered by Island Records founder, Chris Blackwell, who was trying to find songs for his young artist, Millie Small, to record. Changing the spelling to read ‘lollipop’ instead of ‘lollypop’, Millie’s version was recorded in a similar Shuffle/Ska/Bluebeat-style, and in 1964 it became her breakthrough blockbuster hit in the United Kingdom, reaching #2.

“Considered the first commercially successful international ska song, Small’s version of ‘My Boy Lollipop’ sold over six million records worldwide and launched Blackwell’s Island Records into the mainstream of popular music. It remains one of the best-selling Reggae/Ska recordings of all time.”

Millie Small, “My Boy Lollipop” (1964):