Both Originated on the Island of Oahu
When Cindie and I first met, it was because she wrote a letter to me when I was stationed at the Naval Air Station at Barber’s Point. That is another story, but it started a chain of letters back and forth. One fun thing is to try to guess something about the other person. Cindie knew my middle initial was “L”. Her middle name starts with “L” too. My memory says that I jokingly told her my middle name was “Lollipop.” Her friend, Cindy Banner, ran with that and called me Lollipop.
My Boy Lollipop sung by Millicent Dolly May Small

Yesterday, as I was driving to Menards to get some things for Cindie, I tuned the Sirius XM radio to Sixties on Six. That was my music during my teen years. I heard Simon and Garfunkel’s Sound of Silence, Ray Stevens’ Mr. Businessman, and then “My Boy Lollipop” by Millie Small. As soon as I heard Millie’s song I thought of the time when I was called Lollipop. Here is a link to Millie’s version of the song: My Boy Lollipop
Another Nickname
My second nickname was given to me by my fellow sailors in the NAS Barbers Point Refueler Pool. We met every morning in a mobile home that was the office and dispatch for trucks. Our “chief” was Master Chief Petty Officer Messervy (E-9). My recollection was that he was an “Aviation Boatswain’s Mate.” That is someone you don’t want to mess with. The nickname I was given was “Sunkist.” Every day I would bring an orange with me from the mess hall for a snack. My daily orange became my handle. Feel free to call me by either name. It will make me smile.
Millie Small version – “My Boy Lollipop”
Wikipedia also has some additional information about the song’s history. Here is some of it:
In a 2010 interview, Island Records’ founder, Chris Blackwell, told how he came to use “My Boy Lollipop” for Millie’s second British single: “I would go to New York now and again and buy records and sell them to the sound system guys in Jamaica. One of these records was the original version of ‘My Boy Lollipop’. But I’d make a copy of each one on a reel-to-reel tape, it was before cassettes, and when I brought Millie over to England I sat down trying to work out if we can find a song for her and I found this tape which had the original version of ‘My Boy Lollipop’ and I said, ‘that’s the song we should do,’ so it was really really lucky that I found the tape.”
Blackwell had purchased the original record in 1959 and found the copy in his archives in 1963. He went on to produce Millie Small’s remake, changing the spelling of the song’s title to read “Lollipop” instead of “Lollypop”. It was recorded in a rhythmically similar shuffle/ska/bluebeat-style,[10] and in 1964 it became her breakthrough blockbuster hit in the United Kingdom, reaching No. 2, kept from reaching top spot by Juliet by the Four Pennies. The song also went to No. 1 in Republic of Ireland and No. 2 in the United States (on the Smash Record label, behind “I Get Around” by the Beach Boys). Considered the first commercially successful international ska song, Small’s version of “My Boy Lollipop” sold over six million records worldwide and helped to launch Island Records into mainstream popular music. It remains one of the best-selling reggae/ska hits of all time.
Wikipedia LINK Millie Small