The only song from the sessions that ever made Sinatra’s gig rosters was “Lady Day,” a mellow, album-less single that seemed to have nothing to do with the larger concept. Sinatra would present the song as a tribute to billie holiday, who died of liver damage about 10 years earlier. Even with its elegiac tone, the words are sweeter and sweeter than anything on the record. “His morning came too soon, too soon,” Sinatra sings, “and died before afternoon.” It’s sad, but, in his story, it also sounds a bit like relief.
A common line about Sinatra is that he couldn’t sing what he didn’t feel, which, like much inherited wisdom about Sinatra, seems to be half true. After all, he’s recorded as never enjoying playing chestnuts like “Strangers in the Night” or “My Way”, and throughout the 70s and 80s he recorded a lot of ill-fitting material that might have sounded overdone, even then say “Sweet Caroline” or “Just the Way You Are”.
When Gaudio and Holmes sent Sinatra their home demos of the material (“Who’s got the nerve, at 28, to sing a demo for Frank Sinatra when you’re not a singer?” Gaudio reflected earlier this year), they were under the impression that he would only choose a song or two. Instead, he was taken by the whole project. Perhaps it was the recent death of his father and the sympathetic portrayal of parenthood songs from a man’s point of view. Perhaps it was his portrayal of a woman leaving her marriage to pursue her life in the big city, as he had recently served Mia Farrow’s divorce papers while she was in Los Angeles on the set of Rosemary’s baby. (Sinatra had asked Farrow – his wife of two years, almost 30 years his junior – to drop the project and meet him in New York, where she would star in her own film, The detective. “While she’s working for us, she’s Mia Farrow, not Ms. Sinatra,” a producer allegedly told her. It was the last straw.)
In the decades to come, Sinatra had more success ahead of him. His rendition of “New York, New York”, released in 1980, would eventually replace “My Way” as the closest to his concerts. He would also return to his saloon ballad comfort zone in 1981 She shot me downbringing together arranger Gordon Jenkins for the last time to follow the thread of his more characteristic breakup songs of the 50s and 60s. He even returned to the movies, some seven years after dirty dingus. Who leaves everything Watertown in a vulnerable position, documenting an artist at rock bottom, freed from widespread indifference, paving the way for the first moment in a long career where he felt nothing important awaited him.
There is a certain irony in this set of songs – written specifically to avoid the common tropes of Sinatra’s image, already set in stone in 1970 – aligning so closely with his personal life at the time. But any autobiographical symmetry dissolves when the music plays. Unlike “Lady Day”, which Sinatra could interpret as his own remembrance of a lost colleague, there was no way to fit these songs into his larger oeuvre. A charming gentleman in an expensive tuxedo does not sing “Goodbye (she says quietly)”. “Michael & Peter” wouldn’t make sense to a casino audience. Try telling the narrator of “For a While” that the best is yet to come. These songs stand out, and so Sinatra kept them out. In their words – full of anticlimaxes and dead ends, loneliness and nostalgia, small towns and gray skies, empty trains and unsent letters – there was a story close to his heart, a story as serious than life and death. It wasn’t the story he had set out to tell, or the one the world wanted to hear from him. But that was the story anyway.
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