Paul Anka was only 16 years old when he skipped school in Ottawa, flew alone to New York City with a suitcase of demo tapes, and convinced a record executive to gamble on a song about a girl who barely knew he existed. The girl’s name was Diana Ayoub. She was an older teenage babysitter in his neighborhood in Ottawa, Canada, and Anka had been quietly obsessed with her for months. She was 18, elegant, and far out of reach for a shy high-school student who spent most evenings playing piano and writing songs in his parents’ living room. But that crush turned into a melody. In 1957, Paul Anka borrowed $100 from his uncle, paid for a small recording session in New York, and cut a rough demo of the song he had written for her. Most record labels barely listened. Teenagers writing their own songs were not taken seriously in the 1950s. The music industry was controlled by professional songwriters in places like New York’s Brill Building. A 16-year-old Canadian showing up with a homemade love song looked more like a curiosity than a business opportunity. Then Anka walked into ABC-Paramount Records. Producer Don Costa agreed to hear the demo. The recording was simple: piano, light orchestra, and a teenage voice begging a girl not to leave him. Costa heard something others had missed. The label released “Diana” in July 1957. What happened next shocked the entire music industry. The song exploded on radio. Teenagers across North America began requesting it constantly. Within months, “Diana” sold over 9 million copies worldwide, becoming one of the biggest pop hits of the decade. Paul Anka was suddenly a global star before finishing high school. But the story did not stop there. More than a decade later, in 1968, Anka found himself sitting across from Frank Sinatra at a dinner in New York. Sinatra had recently announced he might retire from music. He felt disconnected from the younger generation dominating the charts. Sinatra needed one final song. Anka listened