Song of the Day 4/17: Little Millie Small, “My Boy Lollipop”
Guest post by Nathan Arizona
Before there was Bob Marley, there was Little Millie Small.
Little Millie had the very first Jamaican hit in America with a 1964 ska song called “My Boy Lollipop.” It was a snappy tune you could dance to, heavy on the island backbeat but spun from American R&B like other ska songs.
A decade later the prevalent Jamaican style was reggae and Marley was king. Reggae was slower than ska, more for nodding along to than dancing. It was at home on hippie-style FM radio, not the Top 40.
Little Millie Small was one and done. Bob Marley was Bob Marley.
Ska and America were not total strangers. It was created around 1960 by Jamaican musicians who’d listened to a lot of R&B coming from New Orleans radio stations. Rock Hall of Famer Fats Domino was a favorite because they liked how he came down hard on the offbeat. His 1959 song “Be My Guest” is considered one of the most important influences on ska. When music from New Orleans got harder to find Jamaicans began to write their own speeded-up version with an even stronger emphasis on the backbeat, mixing it with some Jamaican folk styles.
Millie Small’s “My Boy Lollipop” was based on another American R&B song that had become popular in Jamaica. “My Boy Lollypop” (different spelling) had been written by a member of the Cadillacs and recorded in New York in 1956, with only moderate success. Like many other R&B songs of the time, it featured the “shuffle rhythm” also adopted by Fats Domino. When Chris Blackwell was looking for a song to jump start his new Island Records’ Jamaican division he chose that one and brought 17-year-old Small to London from Jamaica to sing it. To give it a greater ska flavor than the original he also recruited Jamaican guitarist Ernest Ranglin to produce.
“My Boy Lollipop,” credited to “Millie,” no last name, reached No. 2 in the U.S. and U.K. and sold 7 million copies worldwide. It was the last Jamaican hit in the States until Desmond Dekker’s “Israelites” in 1969. By that time the prevailing style was the smoother, darker rock-steady. Soon to come was the still slower, politically aware reggae of Bob Marley and others. That’s when Jamaican music became a bigger worldwide phenomenon than even Little Millie Small.
Here’s Little Millie Small, all the way from Jamaica.
And here’s the song with Fats Domino’s rolling piano and heavy backbeat that paved the way for ska.


I was fifteen in the Cayman Islands when Milly Smalls song hit. Big, big deal at the time. Thanks.
Another ska root from Fats: https://www.youtube.com/watch?v=QLgY-bg5CHY