During the interview, the renowned English singer-songwriter shared stories behind the record's songs, and offered several anecdotes about his own youth, which inspired much of The Boy Named If (And Another Children's Stories).
Reflecting on "The Death of Magical Thinking", for instance, Costello revealed that the song's central metaphor was related to the time he spent living in the flight path of London's Heathrow Airport when he was a child. "I was trying to think of an image that really encapsulated the conundrum about the fear and thrill of this transition from innocence to awareness, and it was flying", he shared. "When I was a boy, my ambition was to be able to go to Heathrow Airport and buy a ticket to everywhere. But guess what happened? I became afraid to fly. I became deadly afraid to fly when I was 16 and didn't fly until I was 22, 23. It was the perfect metaphor for fearlessness".
But not all of the tracks on the album are autobiographical. The album's third track, "Penelope Halfpenny", for example, paints the picture of a secondary school teacher "who is a person, not somebody covered in chalk dust", Costello explains. "She is a young woman who is clearly not really suited to her apparent vocation. She probably hankers after a [different] life. The short story version hints at the fact that she was a journalist and she wants to be in espionage or something. She wants a more dramatic life than teaching English Literature to a bunch of know-nothing little kids that are just horrible, snotty teenagers".
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