Michael Caine has recalled the moment he was left completely starstruck by his close friend Frank Sinatra, despite the two-time Oscar winner having grown accustomed to Hollywood's elite after moving from Britain to the United States in the 1960s. Caine, a working-class Londoner, became unexpectedly close to Sinatra after dating his daughter Nancy, with the singer treating him to experiences such as private jet travel and trips to Las Vegas that were previously unknown to him.

Speaking to GQ, Caine described Sinatra as generous and fond of teasing him about his Cockney accent and prolific film output. He revealed that during one flight, left alone with Sinatra as the rest of their party travelled separately, he suddenly froze and grew tongue-tied upon realising he was sitting beside a man he had idolised since childhood, telling Sinatra he felt "overwhelmed" before needing a moment to compose himself.