“My Boy Lollipop” by Millie Small
As is alluded to in the trivia section, “My Boy Lollipop” is a song which has a strong teenage feel to it. In other words, the lyrics read like a girl’s admiration for her boyfriend. And as is the sentimental thesis of the track, they primarily focus on her admiration, i.e. love, for him.
The title of the song, as you have probably already deduced, is based on a metaphor in which she is comparing him to a lollipop. And in that regard he is indeed “sweet as candy” and her “sugar dandy”. And besides that she also states her undying commitment to their relationship, expressing that she also idealizes if he behaves likewise.
So all things considered, the easiest way to describe the situation at hand is that the singer, a young lady, is in love. And the guy who she is in love with, i.e. the addressee of the song, is her “boy lollipop”, i.e. the object of her affection.

Facts about “My Boy Lollipop”
“My Boy Lollipop” was written back in the 1950s by Robert Spencer alongside Johnny Roberts.
It was first initially recorded by a singer from Brooklyn named Barbie Gaye. And like Millie Small she was a teenager at the time.
Millie herself was 17 years old when she recorded her rendition of the song.
The genre of music Millie’s version of “My Boy Lollipop” is generally classified under is called ska/reggae. Ska is a genre which is commonly known as the predecessor of Jamaican reggae. And whereas reggae has gone on to become a global phenomenon, ska never took off like that. As such this is not only the first songs of that genre to achieve international success but also only one of a handful to ever do so anyway. And even in terms of being classified as a reggae track, it has also proven to be one of its top sellers in music history.
This track reached number two in both America and Britain. It performed likewise in Australia, Canada and New Zealand and subsequently was considered the signature song of Mille Small’s career.
It terms of sales it has sold in excess of 7,000,000 copies around the globe. In fact the song was so successful it is credited with giving Island Records, the company that published it which is now a household name in the music industry, its first notable hit. Indeed it was Chris Blackwell, the founder of Island, who personally brought Millie Small over from Jamaica to the UK to record the song.






I was just a little boy when I came to fall in love with this piece of a song and it was around late fifties or early sixties. As a mere rural boy who grew up where there was no schooling in that part of South Africa, I just couldn’t believe there was such a person with childish voice intonation that I found hard to believe there were such a real human being with such an unparalleled refined voice. It was my late uncle that had a gramophone who played this song. I believe this song must have been one of the few white language song if not the only one in his traditional African Song collection. As an author of novels, it fills like I could go on and on in adoring this piece of song and Millie, more especially Millie was just a mere teenager but however, took the world by storm,. Even today, it feels like I could play this son non-stop amidst today’s songs played by highly advanced artists as well as highly advanced technological musical instruments. Millies’ song remains undiluted up to this day. God Bless Millie!
Hi Sonty, thanks for your beautiful contribution.
It seems to me that she is singing about enjoying doing oral sex on her boyfriend. I think that is the hidden meaning, and Millie may not have thought about this herself, but I believe the implication is there.