Known for his iconic ballads and captivating stage presence, Frank Sinatra was also fiercely dedicated to keeping up appearances. This protectiveness extended beyond the music world, influencing his relationships both personally and professionally – occasionally in unforeseen ways.
One such event involved stand-up comedian Don Rickles, whom Sinatra considered both “his dearest friend” and a personal provocateur who walked a razor-thin line onstage. Throughout their relationship, Rickles’ brutally honest “set pieces” often targeted guests, including Sinatra himself, leaving the audience roaring with laughter on account of being both wildly offensive and brilliantly delivered.
Their interactions seemed to oscillate between genuine camaraderie – Rickles even joked on numerous occasions having a special place booked for himself whenever Sinatra graced Carnegie Hall – and heated exchanges that underlined Sinatra’s deep-seated need to remain in control. It was no easy thing, controlling an audience as fickle as they are in front, especially while navigating the unpredictable waves of comedy.
However, according to eyewitness accounts recounted many years afterwards, a performance at Washington’s Waldorf Astoria ballroom pushed Rickles beyond any boundary set by Sinatra himself. During a routine aimed at Sinatrauite regulars on floor level and friends seated behind a podium where Sinatra sat during the show – Rickles went particularly hard on one individual audience member – an actress named Shirley MacLaine.
The performance saw Rickles’ trademark biting humour, but with sharper barbs aimed directly at Maclaine. This wasn’t just playful ribbing; things escalated from observational humor to something far more demeaning and uncomfortable.
Witnesses claimed a visibly enraged Frank immediately summoned his security team at the sight of it.
They escorted the offending comedian right offstage, effectively halting Rickles’ act in mid-flow and silencing him for that night. Sinatra, with characteristic composure – but clearly frustrated– made only two short public statements: to explain the interruption and apologize both to Mrs. MacLaine for her distressand also (most importantly) reaffirm the high caliber he intended all attending performances would be held to. After much heated arguing behind closed doors between them in late ‘fifties-era showbusiness, they settled down – reconciled – eventually finding their footing around each other again after a considerable cool-down period
It’s an anecdote both comical and cautionary. This short saga highlights the complexity of Sinatra’s relationships, his capacity to orchestrate both brilliance and tension onstage, the importance of ‘protection even beyond mere personal reputation in the celebrity environment he lived in
The act’s termination ultimately speaks volumes about Frank Sinatra’s formidable sway – even over someone known, ironically, for tearing apart facades . It paints a vivid picture of showbiz politics where genuine relationships can be fragile, especially under pressure on live platforms.
