Songfacts®:

• Here, Elvis Costello conjures up a secondary school teacher that's unsuited to her vocation. For Penelope Halfpenny, teaching English Literature to a class of horrible teenagers lacks the excitement of her previous jobs in espionage and as a journalist.
• From her days reporting the Scotland Yard blotter
  Who got who and who got what
  But none of that mattered, not one jot
  To Penelope, Penelope, Penelope
  Penelope Halfpenny
  
  Costello based Penny Halfpenny on an actual teacher he'd had who shared one of her names. "I think she'd stumbled into the life of education from a career in espionage," he told Uncut magazine. "She said she'd been a Scotland Yard crime reporter at one point. She'd talk quite a lot about her life. 'I was at this party in Knightsbridge...' Knightsbridge! I never met anybody who went to a party in Knightsbridge. She sat on the edge of the desk in a short skirt, flicking her hair. She had a hand on the door to a world we hadn't entered. She offered the sense of freer life that we were not being trained for."
• Critics have compared "Penny Halfpenny" to another song inspired by a formative female in Costello's younger days. "Veronica," from Costello's 1989 album Spike, was influenced by the singer's grandmother.
• Costello recorded the song for The Boy Named If. Co-produced by the singer with Sebastian Krys (Carlos Vives, Luis Fonsi), he described it as an album that will "take us from the last days of a bewildered boyhood to that mortifying moment when you are told to stop acting like a child – which for most men (and perhaps a few gals too) can be any time in the next 50 years!"