It goes without saying that to record a Beatles’ song has inherent risks, but to record two Beatles’ songs on the same album is really putting yourself out there. Ciofalo acknowledges the risks, “I think there is (a risk), but that is what Miles (Davis) did, (take a tune and do it differently). That is what jazz is to me. You take the tune, listen to it a hundred or a thousand times, and then you start hearing little things inside of it that you may want to pull out. That is your job as an artist, to shake things up, and to make people look at things in a different way.”

After singing with pop bands, Ciofalo decided to get some more voice training at the Juilliard School, noted for its excellent teachers and the caliber of musicians and singers that it turns out. “I thought that I could use some more technique. While singing with the pop bands, I had to simulate a lot of the artists who were out there. At club gigs, they expect you to sound like Whitney Houston, Madonna and all of those people. I was losing some of my classical background, so I went to Juilliard to get those chops back,” she says.

“After Juilliard (and being a pop singer), I went into the big band arena. That was a whole different style of singing. I didn’t know what a big band chart was, until they put one in front of me, and I didn’t know how to read it. They told me to just try to sing something that was like a standard, so I sang “Mean To Me.”  That is how I got that gig. I beat out three hundred people, and I was shocked when I got the phone call to do it. Then I had a lot of homework to do,” Ciofalo recalls.

In preparation for her big band debut Ciofalo listened to recordings by Ella Fitzgerald and Frank Sinatra, to whom she refers as, “two of the greatest teachers a jazz singer could have.” She was also influenced by instrumentalists such as Stan Getz, Louis Armstrong and Houston Person. 

There have been some, hmm, how shall we say, interesting moments during Ciofalo’s career. The singer often played with the big band for daytime gigs, and sometimes it was not possible to find a babysitter for her twin boys who at the time were two years old Mom came up with the ingenious solution of having them hide behind the stands that shielded the musicians’ legs from the audience. Ciofalo thinks that given those experiences, it is not difficult to connect the dots as to why her son’s began playing horns at a young age.

Even Ciofalo refers to the story behind her winding up on stage with Les Paul, in 2001, as a “strange story.” “My husband has a Les Paul guitar, and I said to him that he should go down to the Iridium to have Les Paul autograph it. My husband didn’t have any interest in doing that. I was star struck by Les Paul and thought he was a genius. I told my husband that I was going to take the guitar down to have Les Paul autograph it (she laughs). When I got there, I met another jazz vocalist who knew the person that owned the Iridium. She told the owner that I sang and I was (invited) back to the green room to meet Les Paul. This was just insane. I went down there and met him. He was a sweetheart. I had some flyers about an upcoming performance, in the guitar case and he was looking at them. He asked if that was me and if I sang. He asked me to go up on stage with him to sing a couple of tunes, and he told me that he wanted me to come back again. I did, and that is how I ended up singing at the Iridium with him.”

One gets the feeling in listening to Sun Set, and the air of confidence, but not cockiness that is reflected in Linda Ciofalo’s voice as she talks about her career, that there are numerous other big stages awaiting her.

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