"Bachelor Boy" (written by Bruce Welch and Cliff Richard) was a double 'A' side with "The Next Time" the first of three number one hit singles from the Cliff Richard musical, Summer Holiday. It was followed at number one by The Shadows "Dance On!". The single spent three weeks at No. 1 in the UK Singles Chart in January 1963.

The song was also included on the January 1963 album Summer Holiday. The film was the most successful box-office attraction of the year.

The song is about some advice a father passes to his son, to "remain a bachelor boy until (his) dying day". Richard later commented when he wrote this song he "never expected it to be prophetic". While Richard has never married, the song itself does not rule out marriage, with the final verse stating "I'll get married, have a wife and a child... but until then I'll be a bachelor boy...".

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