A room at Lincoln Hotel. The radio is on. Harry James is sleeping, while his wife Louise Tobin is getting dressed. The voice on radio gets Louise’s attention, she wakes her husband and says “Harry, you might want to hear this kid on the radio. The boy singer on his show sounds pretty good.”

It was June, 1939 when this happened. Harry Haag James had left the orchestra of Benny Goodman, which was quite well known and successful those days, to form his own band.

Harry James

The next night he heard Frank on the radio, he went to Rustic Cabin. He asked the manager where he could find the singer and the manager told: “We don’t have a singer. But we have an emcee who sings a little bit.” Sinatra was the head waiter, chief bottler and sweep-up man in Rustic Cabin.

A singing waiter named Fred Travalena remembers Sinatra. “Frank hated the place, but he knew how to put a plate in front of somebody and he’d do anything to be able to sing” he said later during an interview.

And a young singer in Cabin, Lucielle Kirk, said: “One of the best I’ve ever heard. Every time he opened his mouth, the audience went quiet. He could take the control of an audience just by looking at them. There was a magic about him.”

When Sinatra heard that Harry James was there that night, he started to sing “Night and Day.” “As Frank sang Night and Day, I felt the hairs on the back of my neck rising. I knew he was destined to be a great singer” said James about Frank years later.

That night, James asked Frank to join the auditions for his band. James had reputation, and Frank was very willing to join. Rustic Cabin was no good for him. James also asked Frank to change his name from Frank Sinatra to “Frankie Satin”, because he found the name too much Italian. Frank said “Change it? You kiddin?” Frank had already changed his name once years ago and after his mother Dolly’s reaction, this was not going to happen again.

Sinatra remembers that day. “When he left Benny Goodman and started his own band and came over to see me, I almost broke his arm so he wouldn’t get away ‘cause I was dying to get out of that place.”

Sinatra went to Lincoln Hotel for auditions later. Skeets Herfert explains as following: “Frank walked in with no arrangements. The other guys, who were auditioning for Harry, had charts and everything. But Frank just walked in, walked over the piano player, told him what he wanted to sing, what key he wanted in, and stood up and sang. He knocked everybody out. When the musicians heard Sinatra, that was it. There was no doubt about it.”

“Frank Sinatra” joined the band of Harry James as the vocalist in June 1939 and signed a 2 year contract. Frank Sinatra and Harry James Orchestra played at many places, the first being at Hippodrome in Baltimore on June 30 1939, and they even recorded 10 songs together. The songs were as following.

From The Bottom of My Heart
Melancholy Mood
My Buddy
It’s Funny to Everyone But Me
All or Nothing At All
Here Comes the Night
On a Little Street in Singapore
Who Told You I Cared
Ciribiribin (They’re So in Love)
Every Day of My Life

(All the songs were arranged by Andy Gibson)

Frank Sinatra Harry James 1939

Among the songs they recorded, there was a very special song. It was “All or Nothing At All.” Lyrics by Jack Lawrence, music by Arthur Altman. Though the song sold only around 8500 in 1939, 4 years later when it was released by Columbia Records again it was going to sell more than 1 million in a short time.

But things were not going as good as they expected in 1939. The records sold around 8000, being far away from being a hit, and they even played for very few people sometimes. Meaning? They were broke and unsuccessful.

Frank Sinatra Harry James Orchestra 1939

Once they were playing in Chicago’s Hotel Sherman and the great band leader Tommy Dorsey was also there. One day Frank found a note saying that Tommy Dorsey wanted to see him. Dorsey needed a vocal since the vocal of his band had left. He offered Frank $100 a week (some sources say $110.) Let’s hear the rest of the Frank Sinatra – Harry James story from Frank Sinatra’s words.

“Harry James was one of the finest men I’ve ever known in my life. To tell you the kind of man he was, I had signed a 2 year contract with him, and when I was offered a job within the Tommy Dorsey orchestra 6 months later, Harry took the contract and tore it up. All he said to me was be sure to get more money that I was able to pay you.”

Harry James later told: “Nancy was pregnant, and we weren’t even making enough money to pay Frank the $75 he was supposed to get. So he went with Tommy Dorsey and I said, well if we don’t do any better in the next six months or so, try to get me on too.”

Frank Sinatra remembers those days as “a wonderful six month experience” and Harry James as “a real nice guy with real know-how as a musician.”

When Harry Haag James died in 1983, Sinatra said to Nancy Jr: “He made it all possible for us…”

Frank continued till January 1940 with Harry James. After the last show, Harry James and the musicians left the town. “The bus pulled out with the rest of the guys” Sinatra remembered. “I’d say goodbye to them all, and it was snowing. There was nobody around, and I stood alone with my suitcase and watched the tail-lights disappear. Then the tears started… There was such spirit and enthusiasm in that band.”

Frank Sinatra Harry James Band 1939

It is very clear that Sinatra really loved Harry James, but he had to leave to achieve more. Though James seems older than Sinatra in pictures, he was 3 months younger than Sinatra and no doubt that he was a nice and modest guy. Considering that Dorsey caused a lot of trouble because of the contract later, Harry James was generous enough to tear his contract with Sinatra apart. He wasn’t selfish, and he wanted the best for Frank. And for Frank Sinatra, it was either all, or nothing at all…