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When Sinatra met Humphrey Bogart, the star of Casablanca and The Maltese Falcon said that he’d heard Sinatra knew how to make women faint. “Make me faint,” Bogart said. Sinatra’s faint-inducing ability was also on the agenda when he met Franklin D. Roosevelt. “Fainting, which once was so prevalent, has become a lost art among the ladies,” the president told Sinatra in the White House on September 28. “I’m glad you have revived it.” Then the commander in chief asked Sinatra how he did it. “I wish to hell I knew,” Sinatra said.
The singer had wrangled the White House invitation when the Democratic Committee chairman asked his pal, the restaurateur Toots Shor, to a reception. FDR was glad to host Sinatra; it would counteract Bing Crosby’s endorsement of his opponent, Republican Thomas E. Dewey, governor of New York, Roosevelt’s old job before he went to the White House. “Look who’s here,” Roosevelt exclaimed and asked the singer to confide the title of the song that would be No. 1 on the hit parade next week. “I won’t tell,” FDR grinned. “Amapola,” Sinatra said. (The title may have sounded Italian to the president—and Italy was an uncomfortable subject in wartime—so he switched the subject.) The meeting went well, though the president was said afterward to scratch his head in wonderment at the idea that the skinny crooner had revived what he called “the charming art of fainting.” “He would never have made them swoon in our day,” he told an aide after the party broke up.
Sinatra joined Bogart and Bette Davis, Rita Hayworth, Orson Welles, Danny Kaye, and Edward G. Robinson on the FDR bandwagon in 1944. With his talent for friendship, Frank and Welles in particular got to be great buddies, and when Orson and his wife Rita Hayworth had a baby that December, they chose Sinatra to be the girl’s godfather. There was a rally for an unprecedented fourth term for FDR in Fenway Park on the weekend before Nov. 7, Election Day. The Boston Globe reported that Welles and Sinatra—“the dramatic voice” and “the Voice”—brought the house down. On Election Night, the two men had rooms at New York’s Waldorf Astoria but before retiring they downed a few celebratory drinks and figured out a way to harass the conservative Hearst columnist Westbrook Pegler, who regularly attacked President Roosevelt. Pegler had dubbed Sinatra the “New Dealing Crooner,” “bugle-deaf Frankie boy,” and probably a red. Welles had his own reasons for detesting the Hearst chain, the head of which did not look kindly on Welles’s Citizen Kane.
Sinatra donated money to FDR’s campaign, made radio broadcasts, spoke at Carnegie Hall. “I’d just like to tell you what a great guy Roosevelt is,” he said. “I was a little stunned when I stood alongside him. I thought, here’s the greatest guy alive today and here’s a little guy from Hoboken shaking his hand. He knows about everything—even my racket.” Conservative columnists predictably had a field day with Sinatra’s self-importance. At a concert Sinatra sang a parody lyric of “Everything Happens to Me.” The Republicans were “mad as they can be,” because he went to Washington to have a cup of tea with “a man called Franklin D.”
For more from this excerpt from Sinatra's Century: One Hundred Notes on the Man and His World, click here.
https://www.thedailybeast.com/when-sinatra-campaigned-for-fdr
