“I’ll Never Smile Again” by Tommy Dorsey

At #1: July 27, 1940 – October 12, 1940 (12 weeks)
Still alive? No. Dorsey died on November 26, 1956
Extra info: Frank Sinatra is the vocalist



Imagine that you are fifteen years old and living in the United States in 2012. Assume that you’re downloading the latest hit by Lady Gaga into your iPod and after the download, you hit “play”. But instead of Lady Gaga you get “I’ll Never Smile Again” by Tommy Dorsey. What would be your initial reaction?

You’d know something was wrong right away. You’d listen to the chorus for a few seconds, thinking that Lady Gaga was putting you on, but after thirty seconds you’d probably conclude that you downloaded the wrong song. There’s no escaping the fact that this song is a musical relic, an object of some extinct era. There’s very little connection between this song and anything your peers are listening to now – at least none that you can figure out.

It’s a very slow song. There’s none of the bombast associated with a modern song. It’s a very sentimental song, which focuses on capturing the smoothness of the singer’s voice. There’s no “rock sensibility” – these days, a certain gracelessness in presentation is expected because it denotes honesty and authenticity. Instead, this song showcases technical proficiency. Clearly, it’s supervised; there is no “jamming”. There’s no improvisation, everyone is on the same page from the first note. You could compare it to classical music, which probably would have been a scandalous comparison to any longhair living in 1940.

So where’s Tommy Dorsey? Is he the singer? No, that’s Frank Sinatra. Okay, maybe he wrote the song. No, he didn’t write the song either, that was Ruth Lowe. So what did Tommy Dorsey do for this song that allows him to stamp his name all over it?

He conducted the orchestra, and probably arranged the song. The song was assembled by Dorsey. Ruth Lowe wrote this song after the death of her husband after he died during surgery. She offered the song to a Canadian performer, but it went nowhere. So she gave it to someone in Tommy Dorsey’s band, hoping that Dorsey would pick it up. Dorsey liked what he heard, and he went with it.

Sinatra had only been in Dorsey’s band as his singer for about seven months or so. He had only fronted a big band since a year before. He had been hired by Harry James just a year earlier, his first big break in show business. Tommy Dorsey – who I understand had no problem with raiding other bands for their best performers – wanted Sinatra. Graciously, Harry James released Sinatra from his contract, for which Sinatra would be forever grateful. (The Chairman would not be so grateful about the terms of Dorsey’s contract, which gave Dorsey a third of Sinatra’s lifetime income.) I’m sure some Frankie fan out there will set me straight, but I believe that “I’ll Never Smile Again” was Frank Sinatra’s first big hit. (Frankiemania would soon follow.)

Even if Dorsey is waving his baton and playing puppetmaster, he has a very light touch. Nothing someone unschooled would ever associate with “Big Band” music. (No loud trumpets, trombones, etc.) Without knowing otherwise, I suspect that Dorsey’s skill was very much like that of a modern day studio producer crossed with a musical conductor. He knew how to put this song together – he crafted it which is why he gets to put his name on it. Frankly, modern music would be a lot more honest if songs were attributed to the engineers in the booth and not attributed to the singers who these days merely provide vocal samples which are autotuned almost to the point of being unrecognizable.

Maybe Tommy Dorsey, if he were alive and at his peak in 2012, would have done the same thing modern studio engineers do if he had access to the technology. What do I think about this song? I think it’s pretty dull myself. Not of my time, although I can understand its appeal. But I do believe that Dorsey would have never sweetened Sinatra’s voice. I don’t know much about music, but Sinatra’s voice is as perfect for this song as you can get.

Okay, enough about the song itself. Why is this song the first Number One song?

According to Wikipedia, Billboard had been tracking popular songs before 1940. They tracked:

• Sheet music best sellers
• Records most popular on music machines (jukeboxes)
• Songs with the most radio plugs – this was limited to New York City

However, this inaugural Top Ten list – called the “National List of Best Selling Retail Records” – was a first attempt at a nationwide poll of record sellers in large cities, from New York to Los Angeles.

It’s odd that the first Number One song of the Number Ones features a great singer – who would dominate the charts for decades, but would not get the first Number One song attributed to him – that would belong to Tommy Dorsey. This is 1940, and the Big Bands roam the world of popular music like dinosaurs. Frankie will have to wait until the landscape changes.

Extra: The Three Stooges made a short subject film in 1941 called "I'll Never Heil Again". Clearly, Tommy Dorsey was on someone's mind at Columbia.