Frank Sinatra Said Ronald Reagan Was a ‘Stupid Bore’ Who Couldn’t Land Roles

Frank Sinatra was entirely, often brutally, honest about his opinion of other celebrities. When Ronald Reagan first made the switch from a career in film to one in politics, Sinatra made his opinion of the other man clear. He expressed distaste for both Reagan and his wife’s acting abilities. Later in life, though, Sinatra’s opinion of Reagan shifted dramatically.

A black and white photo of Frank Sinatra, Nancy Reagan, and Ronald Reagan in 1955. They stand in a row and smile.
Frank Sinatra, Nancy Reagan, and Ronald Reagan | Hulton Archive/Getty Images

Frank Sinatra was once close friends with John F. Kennedy

In his lifetime, Sinatra would be close friends with both John F. Kennedy and Reagan. He befriended the former before he ran for president. Sinatra’s friend and fellow Rat Pack member Peter Lawford married Kennedy’s sister, which is likely how they met. When Kennedy ran for president, Sinatra threw his whole weight into the campaign.


Sinatra publicly endorsed the politician, hosted donor events, and openly referred to him as the next president of the United States. When Kennedy won the election, Sinatra performed at the pre-inauguration gala.

“His love for Kennedy was so strong,” his daughter Nancy Sinatra said, per the Daily Beast. “JFK was his friend. For the patriotic American dreamer, this was the ultimate compliment: The President of the United States was his friend.”

Ultimately, though, their friendship fractured when Robert Kennedy grew uneasy over Sinatra’s alleged mob ties. Kennedy intended to stay at Sinatra’s house while visiting California but stayed with Bing Crosby instead. Sinatra destroyed the presidential suite and helipad that he had specifically constructed for the visit. He would hold a grudge against Robert Kennedy for the rest of his life.

The ‘My Way’ singer expressed his contempt for Ronald Reagan’s acting

In her memoir My Lucky Stars: A Hollywood Memoir, Shirley MacLaine detailed her friendship with Sinatra. In it, she explained that Sinatra held a deep disdain for Reagan as an actor.

“He told me that he thought Ronald Reagan was ’a stupid bore who couldn’t get a job in pictures, which was why he went into politics,’” she wrote, per Vanity Fair. “He threatened to move out of California if Reagan ever got elected to public office.”

Sinatra also believed that Reagan’s wife, Nancy Reagan, was not a strong actor.

“He thought Nancy was ’a dumb broad with fat ankles who couldn’t act,’” MacLaine wrote. “I heard him scream and curse at the television set when they appeared.”

Sinatra’s well of contempt for the Reagans was not endless, however.

Frank Sinatra eventually befriended Ronald Reagan

Eventually, Frank Sinatra softened his opinion on the Reagans. Whether this was because of his shifting politics or, as MacLaine believes, an ongoing grudge against Robert Kennedy is unclear. Regardless, the two men became friends, and Sinatra endorsed Reagan when he ran for president.

According to the Desert Sun, Sinatra became particularly close with Nancy Reagan. He made her cry when he sang “Nancy (With the Smiling Face)” at the first inaugural ball. He also immediately flew to Washington DC to be by her side after the assassination attempt on Reagan in 1981. When Sinatra’s mother died in 1977, Reagan attended the funeral. Nancy Reagan was also in attendance at Sinatra’s invitation-only funeral in 1998.

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