The first ever love song penned by Hammond was a story of true love, inspired by a girl he saw in Gibraltar when he was 16. He explained on his website: "A big ocean liner docked in Gibraltar (that's where I'm from) filled with school children of all ages from Scotland that were touring the Mediterranean. I had a skiffle group then called The Diamond Boys and we were asked to play on board for the students. That's where I noticed a girl with blue eyes and ginger hair that stood out from the rest, she sat in the front row and smiled at me all through the performance. Later we walked around the ship for a few hours holding hands, I kissed her goodbye and the ship sailed away, I was never to see her again, the sadness I felt that moment brought tears to my eyes so I went home strummed my guitar and wrote my first love song called 'Blue Boy,' for this girl named Ann Andrews."
Ann was eventually tracked down and they met for the first time since their teenage brief encounter on the BBC 1 program The One Show on March 27, 2013.
Hammond's Skiffle group, The Diamond Boys, had no real commercial success, but they performed at the first nightclubs in Madrid to stage modern bands alongside Spanish rock and roll pioneers such as Miguel Ríos. In doing so The Diamond Boys played a part in Spain's introduction to pop and rock music.