
“Lot of bigotry”: the two musicians Frank Sinatra was most proud to work with
Frank Sinatra might have the most impressive collaborative discography of any great musician – Ella Fitzgerald, Louis Armstrong, Dean Martin, Aretha Franklin, Bono, and Barbra Streisand, to name just a few, but it was none of these that he admitted to being most proud to work with.
In 1964, Sinatra released the studio album It Might as Well Be Swing, accompanied by the iconic Count Basie and his orchestra – the project was also produced by the legend Quincy Jones, and would mark the first of their lengthy friendship together in the booming technicolour world of jazz, it’s this mind-melting, hopping and skipping project that Sinatra would look back on with the most fervent ebullience.
“What I remember about it was that it was probably the most exciting engagement I have ever done in my life since I have been performing. The Basie orchestra, as you probably know, was like a juggernaut that came at you. You knew that you had to be a part of that, or you got lost,” Sinatra recalled. Sure enough, the album is an explosion of texture and heartfelt colour.
Watching someone hone their craft to an impossible degree that they can distil it down to its rudimentary parts was a mind-blowing experience for the singer, too: “Basie, of course, really never conducted the orchestra; he sat at the piano, and if you’ve ever seen him work, he would never use more than three or four keys. He’d just make wonderful sounds.” Like a lengthy Pink Floyd song that’d leave a crowd floundering in silence, transfixed long after the final note, Sinatra was completely pulled into the Basie sonic journey.
However, it wasn’t just the triumphant sonic experience that Sinatra had during the collaboration that made him most fulfilled; Sinatra had so much to learn from the huge personalities of both black geniuses, and in 1964, racial segregation was legally dismantled by the Civil Rights Act of 1964, which outlawed segregation in public spaces and schools, a landmark movement in the right direction during the systemic racism of the Jim Crow era.
Nonetheless, President Lyndon B Johnson’s pen on a dotted line didn’t just mean that the unjust treatment of non-white people halted. When working with Basie’s orchestra, held together and taken care of in this instance by Jones, Sinatra noted that each day after the congregation of bodies split, the black performers would leave via an entirely different route.
He quickly realised that, due to their skin colour, the musicians lived on the other part of town: “I don’t know whether it just meant Vegas, or Tahoe, or what, but I think it meant the whole state. There was a lot of bigotry involved then; I began to make noise about it. A few threats like ‘I’ll walk, I’ll go back to LA, get yourself a new boy’.” Sinatra simply couldn’t understand the reason behind the ghastly separation.
During the interview, he added, “Whether they’re pink, black, yellow, or tan, I don’t care. If he performs well, that’s the man I want to work form, it doesn’t make any difference,” with Sinatra put his foot down and hollering, “I was the biggest mouth in the town – in short, I loathe bigotry of any kind,” seemingly more media-trained back then than most celebrities today.
Jones, Basie and Sinatra made glorious music together, and would go on to complete globally celebrated tours, but in the end, Sinatra was most proud because of what they could do together for their community, and what’s more important than that?


