The Truth About Frank Sinatra And Billie Holiday's Relationship

Billie Holiday and Frank Sinatra were both born in 1915 — she in Philadelphia and he in Hoboken, New Jersey, eight months later. As T Magazine notes, the two occupied different places in the professional music industry. Holiday is remembered for her collaborations with jazz saxophonist Lester Young, while Sinatra found fame and fortune working with the legendary arranger Nelson Riddle. He survived several career ups and downs — was often despised by the public, even — to ultimately reach superstardom and die a millionaire at 82. Holiday's bank account contained 70 cents when she died at the age of 44 in 1959. However, the reality is that we wouldn't have one without the other.

Sinatra was absolutely floored when he first saw Holiday sing in a Manhattan nightclub in the late 1930s. He even got some singing advice from her, which Lady Day downplayed. "I told him certain notes at the end he could bend," she said. "Bending those notes — that's all I helped Frankie with." However, even if her touch on his art was as light as she'd claimed it to be, Sinatra was forever grateful. "It is Billie Holiday ... who was, and still remains, the greatest single musical influence on me," said Ole Blue Eyes in 1958, the same year that Holiday released her album Lady In Satin, the first track on which was Sinatra's "I'm a Fool to Want You," which he himself co-wrote.

When we listen to Sinatra's boundless, bombastic optimism on songs like "Come Fly with Me" and "I've Got the World on a String," or the sultry seduction in tunes like "Witchcraft" and "I've Got You Under My Skin," or the absolute dejection sung from the gutter in "One For My Baby" and "In the Wee Small Hours of the Morning," we're hearing what the Chairman learned from Billie. As noted by L.A. Magazine, Sinatra claimed that all subsequent singers had been "touched ... by her genius." He said that "what she did was take a song and make it hers ... she lived inside a song."

And indeed this is what both of these singers appear to do in the tunes they stapled into the American songbook. Although Holiday boasted no more than an octave in her voice that admittedly lacked the acrobatics of singers like Ella Fitzgerald (whose range spanned three octaves), Holiday entered and existed within a song the way a character in a novel makes bad decisions, drinks too much, takes on the wrong lovers, and gets her heart broken every step of the way. And in no other singer of American jazz and swing standards is this more apparent than in Frank Sinatra. Just as he did multiple times in real life, he could live ecstatic highs and bring us to the edge of self-oblivion in the span of a three-minute pop song, and he learned how to do this from Billie.

In his 2003 memoir Mr. S: My Life with Frank Sinatra, the Chairman's former chauffeur George Jacobs recounts the moment he took Sinatra to see Billie Holiday in the hospital in 1959 as she was dying of cirrhosis of the liver. The singer was under close watch by the police after they'd found heroin in her pocketbook during a raid on her apartment. Jacobs said Sinatra showed off his relationship to Holiday, heaping praises on her for influence. She characteristically played down her role, again saying all she did was show him "how to bend a note ... that's all." Then she pulled him to her so the cops wouldn't overhear and asked him to get her some heroin.

Holiday had struggled with drugs and alcohol throughout her life, and at the end of it, she was withdrawing and in pain. The pain was so apparent to Sinatra that, despite his aversion to drugs, he couldn't bear to see his idol that way, and he did everything he could to get her one last fix. He tried to bribe police, sought out the city's biggest drug dealer, even appealed to the mayor himself, but to no avail. She died of liver failure before he could help her, and he felt like he'd let her down. After she died, Sinatra holed himself up in his penthouse apartment drinking and sobbing as he listened to her records for two straight days.