In the late 1970s and early ‘80s, Frank Sinatra remained an iconic figure in popular culture, despite having reached the peak of his fame decades earlier in the 1940s and ‘50s. His continued relevance during this time, long after his heyday, reflects the immense talent that kept him in the public eye. It’s a curious historical footnote that Sinatra – not Clint Eastwood – was originally considered to play the role of ‘Dirty’ Harry Callahan in the Dirty Harry films. This intriguing tidbit is just one example of how Sinatra bridged the gap between the golden age of Hollywood and the more modern cinematic landscape of the time.
Sinatra’s enduring presence on screen during this period was not just a result of his past glories, but his involvement in several films alongside younger stars that reflected both old and new Hollywood. After winning an Oscar in 1954 for From Here to Eternity, Sinatra’s career remained active, taking him to projects that varied widely in tone and genre. He starred opposite Raquel Welch in the 1968 X-rated thriller Lady in Cement and played himself in the 1984 comedy Cannonball Run II alongside Burt Reynolds. Sinatra, through his versatile roles, continued to be a bridge between generations, whether audiences embraced it or not.
Among his late career films, one stands out not for its quality, but for its fascinating cast: The First Deadly Sin (1980). The film, a crime thriller set in New York, is largely forgotten today. However, it features a significant moment in Hollywood history for one reason: its star-studded ensemble. Sinatra stars as Edward Delaney, a soon-to-be-retired police inspector hunting down a serial killer while caring for his ailing wife, played by Faye Dunaway. Dunaway, already an established star with an Academy Award for Network (1976), brought gravitas to the role. But it’s the inclusion of a young Bruce Willis that would later make the film memorable in retrospect.
At the time of filming, Willis was virtually unknown. His role as “Man Entering Diner as Delaney Leaves” was brief – so brief, in fact, that it can easily be missed. Yet, the experience was unforgettable for the then-25-year-old actor. Willis recalls being struck by Sinatra’s warm and down-to-earth nature, a contrast to his legendary status. “I got to hang around the set, and they were shooting nights, and Frank Sinatra would come out,” Willis later reminisced. “We were shooting in a bar, so we’d just get him talking, and all of the young actors just tried to ask him questions and get him telling us stories.”
One such story involved Sinatra’s time on the set of From Here to Eternity, where Ernest Borgnine encouraged him to hit him with a barstool as hard as possible to make their on-screen fight look more authentic. For Willis and his fellow young actors, hearing firsthand accounts from Sinatra was a memorable and formative experience that left them with their own stories to tell.
At the time, Willis had just begun his career, with The First Deadly Sin being his first-ever on-screen appearance. It would take another five years before he would land the lead role in the hit detective series Moonlighting, and his action-hero future was far from certain. Not even credited for his small role in The First Deadly Sin, Willis’ encounter with Sinatra still stands out as one of the most meaningful early experiences of his career. For him, and for countless other young actors, working with Frank Sinatra was an unforgettable introduction to Hollywood.
