“On a Little Street in Singapore” (1939) Harry James with Frank Sinatra

“On a Little Street in Singapore”

Composed by Peter DeRose (music) and Billy Hill, (lyric); arranged by Andy Gibson or Jack Matthias.(*)

Recorded by Harry James and His Orchestra for Columbia on October 13, 1939 in Chicago.

Harry James, trumpet, directing: Jack Palmer, Jack Schaeffer and Claude Bowen, trumpets; Truett Jones, Dalton Rizzotto and Bruce Squires, trombones; Dave Matthews, and Claude Lakey, alto saxophones; Bill Luther and Drew Page, tenor saxophones; “Jumbo” Jack Gardner, piano; Brian “Red” Kent, guitar; Thurman Teague, bass; Michael V. “Mickey” Scrima, drums. Frank Sinatra, vocal.

The Joy of Swing – Worldwide:

With this post, we celebrate the 375,000th visitor to swingandbeyond.com. This number, and several other metrics, have continually reminded me that there are people everywhere who are either curious about the music and history of the swing era, and/or simply like the music itself. What is most astonishing to me is where these people live. As one would expect, the vast majority of them live in the United States, which is the place where the swing era began, evolved and flourished. The next largest group of visitors to this blog are those who live in the largest nations in Europe. But many other people from countries like Ukraine, Andorra, San Marino and Montenegro also visit. The blog has fans in Estonia, Latvia and Lithuania. Of the Asian countries, Japan has the most visitors to swingandbeyond.com. But there are also people in China and Hong Kong, India, Laos and Kuwait who have visited. And there are many visitors to this blog who live in Singapore. Recently, I have noted an uptick in visitors from Australia.

This blog could not exist without the Internet. As someone who lived for many years before there was an Internet, I can say without reservation that it has expanded the possibilities for people all over the world to enrich their lives in many ways. Unfortunately, like many other human inventions, there is also a dark side to the Internet, which reflects the dark side of human nature. Consequently, the Internet has also proved to be a powerful tool to spread lies, misinformation and conspiracy theories. That is not where we go at swingandbeyond.com.

My theory is that music, by its very nature, appeals to the best aspects of our humanity. It is about joy, sadness, love, contemplation and exhilaration, among other human feelings and moods. Music is magical in that it appeals to us on many levels, some of which cannot be explained. So, as one of my musical heroes (of many), Billy Strayhorn, would say when confronting good news, Onward!

The story:

Frank Sinatra joined Harry James’s band near the end of June in 1939. His initial weekly salary was $40.00. That was raised to $50.00 starting on August 1. That base salary would be augmented by money made on record dates or paid radio work. Although the relatively new James band (it had debuted in early 1939) did appear regularly on radio from the summer of that year through the autumn, those appearances were on sustaining, that it non-paying, broadcasts. So no one in the James band, including Harry, made any money performing on them. After Sinatra joined, the James aggregation he did make a number of recording sessions with them: on July 13, August 17, August 31, October 13, November 8, and November 30. As you can see above right, Sinatra was paid extra only once in 1939 for performing on recording sessions, in October of 1939. Presumably, the $52.50 he received was an aggregate amount for the three sessions that had taken place before that payment was made. (1)

The Harry James band in July of 1939 in Rome, New York. Identifiable faces L-R at table: Claude Lakey (second); Russell Brown (third); Jack Palmer (fifth); possibly Harry’s road manager, Jerry Barrett (sixth); James (seventh); Jack Gardner (ninth); Truett Jones, (tenth); Red Kent (eleventh); Dave Matthews (twelfth). Back row standing: Jack Schaeffer (first); Bill Luther (fifth); possibly Ralph Hawkins, (seventh); Sinatra (eighth).

The Harry James band worked steadily through most of 1939. They began broadcasting from the Madhattan Room of Hotel Pennsylvania in late March. Then they made a series of broadcasts from the Roseland Ballroom in Manhattan in early July, followed by some airshots from a venue in Atlantic City, possibly the Marine Ballroom on the Steel Pier, followed by a return to Roseland. They were broadcast from the World’s Fair in Flushing, New York in late August, and then from the Panther Room of Hotel Sherman in Chicago in late October and into November. Between these dates were many one-night dance dates. The band worked, but as so often was the case, the work they were doing was not generating enough cash to offset the ongoing expenses of keeping a big band together. By the end of 1939, Harry had gone through all of the savings he had accrued in the two years he had worked as the featured trumpet soloist in Benny Goodman’s band, as well as the $7,000.00 loan he had received from BG. (Above left:  summer 1939 – L-R: Ralph Hawkins, Harry James, Jack Palmer, Frank Sinatra and Dave Matthews. The James band was a happy one, but slowly through 1939, money became increasingly scarce.)

Meanwhile, the boy vocalist of the James band, Frank Sinatra, was becoming more popular with the audiences who heard the music of that band. Through a series of events that began with Tommy Dorsey’s boy singer of many years, Jack Leonard, leaving the TD band at the end of 1939, Tommy was looking for a new male vocalist. By late January 1940, that new male vocalist was Frank Sinatra. It was with Dorsey in the years 1940 through mid-1942 that Sinatra began his climb to a place of prominence as a singer. (At right: Frank Sinatra sings on a James broadcast from Roseland Ballroom in New York – July 1939. The girl seated on the bandstand is vocalist Margie Carroll.) (2)

The music:

The song “On a Little Street in Singapore” was composed in 1938, apparently as a free-standing composition which was not a part of any Hollywood film or Broadway show. We can speculate that the song’s publisher may have touted it to Harry James and/or Frank Sinatra. The recording presented with this post was the first the song received. Within the next couple of months, other artists recording it included: Bob Zurke, Jimmy Dorsey, Glenn Miller and John Kirby. Paul Whiteman and Gene Krupa broadcast it but did not record it. In later years, good recordings of it were made by Dave Brubeck and The Manhattan Transfer.

Formwise, the James/Sinatra recording of “On a Little Street in Singapore” is rather straightforward: James plays the melody in the first chorus and Sinatra sings in the second chorus. Contentwise, the arrangement is marvelously colorful, and it is performed expertly by the James band. The exotic mood of the arrangement, intended no doubt to evoke feelings about a far-off and strangely attractive place, and a particular woman there who provided the inspiration for it all, is greatly enhanced by the soft bolero rhythm that undergirds the music. This rhythm is established in the introduction by the saxophones, open trombones and drummer Mickey Scrima’s gently tapped tom-tom, and is carried on through much of the performance. (It is suspended in the bridge of the first and second choruses, thus preventing it from being overdone.) (Mickey Scrima is shown posing with Harry James at right.)

At this early date in his career, Harry was still learning how to present a melody attractively in a ballad performance. His playing, technically excellent as always, is less than convincing in terms of conveying emotion. He was just beginning to add a bit of schmaltz to his sound and vibrato on ballads. Soon, he would hit pay dirt with these devices, much to the dismay of the fans who loved his romping approach to jazz.

The modulation between James’s solo and Sinatra’s vocal is a delight. It provides a dramatic springboard which Sinatra uses very deftly to begin his vocal. The bolero rhythm returns as Frank phrases the lyric in a manner that can aptly be described as lovingly. It is clear from this performance that Sinatra was already quite masterful in subtly but powerfully projecting emotion in his singing. This is one of Sinatra’s best early performances on record. (At left: Frank Sinatra on the backstage phone. Was Tommy Dorsey calling?)

The recording presented with this post was digitally remastered by Mike Zirpolo.

Notes and links:

(*) Although the arrangement on this song has been attributed to Andy Gibson, I think it possible that it may have been written by Jack Matthias. I welcome all authoritative information on this.

(1) The photo of the ledger of Frank Sinatra’s earnings with Harry James’s band in 1939 comes from The Sinatra Treasures, (2004) by Charles Pignone, 16.

(2) Identification of the girl singer, Margie Carroll, who is also in the picture with James and Sinatra from Roseland Ballroom comes from George T. Simon’s review of the James band at Roseland in Manhattan in the summer of 1939. That review appeared in the September 1939 issue of Metronome. Bernice Byers, sang with the James band before Ms. Carroll, and Connie Haines, who joined the James band in early May of 1939, performed in that role after that. Ms. Carroll was evidently subbing for Ms. Haines at the time this photo was taken.

Here are links to more excellent performances by Harry James:






And finally, here is a link to the recording that had a lot to do with introducing Harry James to swing fans:


Here are links to some of Frank Sinatra’s recordings from the swing era, and beyond:





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  1. I’ve learned through decades of listening that I often have a special affection for the early, scuffling years of the various big bands. The rough-and-ready James orch of ’39 is among the first to come to mind. It’s so apparent from their instrumentals — “Sweet Georgia Brown”; “Two O’Clock Jump”; “Flash”; “(Back Home Again in) Indiana”; “I Found a New Baby”; “Avalon”; “Back Beat Boogie” — that the aggregation just wanted to swing, but Harry had enough experience as a sideman to know that romantic vocals were a necessity, if one wanted to be a success. Too, I believe it’s fairly obvious not just from “You Made Me Love You” and beyond but also his solos on Goodman orch and Teddy Wilson small group sides that the trumpet ace had a flair for, and interest in, ballads. For sure, in the nascent days of the James band, the leader had still to hone his interpretive skills in the ballad field, but he at least had loads of technical ability on which to draw as he developed his emotive aptitude.

    The entrancing “On a Little Street in Singapore” was one of the first sides I heard from Frank’s stint with the James crew. I recall being surprised by the exotic arrangement, as it is so untypical of the band’s sound in that early period. The chart sounds to me much more like Jack Matthias’ writing style than Andy Gibson’s. Matthias, whose work I very much admire, exhibited a talent for drama as well as subtlety, both of which we find in this chart. In any case, the arrangement is vastly superior to Art Guenther’s for the Miller band; I love the figures that are assigned to each horn section from start to finish. Mickey Scrima’s tom-tom work, whether evocative of Singapore or not, too, is a delight.

    I have to give credit to Sinatra for his readiness to acknowledge TD’s influence on his singing — given the less than friendly terms on which Frank took his leave from the band. Tommy and Frank as well as Jo Stafford were sneaky breathers, who took quick pauses in unexpected places so that when when the expected spot came up, they were able to soar right through the lyric line on a high note, creating the illusion that they never breathed. Jo had operatic training, so we may believe that anything she picked up from Tommy was stylistic rather than technical. Frank, though, famously admitted to staring at Tommy’s back, wondering why he could never detect the intake of air. I believe it would be safe to say that Frank studied the mechanics of the Dorsey sound, with an awareness of the emotional impact his boss’ playing had. Still, we can hear in Young Blue Eyes’ work with the James band that the singer was already taking great care with lyric content. He was a fervid admirer of Billie Holiday, and I think we may find even in his early sides that faculty for putting his heart into the story and making it his own. Surely, the more a vocalist likes and identifies with the material the easier it is to interpret it in a convincing manner. I’ve never come across anything on Frank’s feelings about “On a Little Street in Singapore,” but he certainly does sound committed to every picturesque line and his tone is beautiful, displaying the delicacy that we see in his later work. Surprising to me is that the lyric is by Billy Hill, whom I tend to associate most with cowboy and generally rustic numbers, apart from “The Glory of Love.”

    … Congratulations on the milestone —

  2. Congratulations on 375,000! I am truly grateful for this blog and all that you put into each post. You’ve made me appreciate artists whom I otherwise would have never given a thought to and also helped me better understand those that I’ve enjoyed for many years. Keep up the excellent work.

  3. I’m sure some will disagree, but to my ear, Harry James had pretty much fully formed his ballad style (including vibrato) by the time he recorded (with Lionel Hampton) “Any Time at All” on July 21, 1938.

  4. My father loved Tommy Dorsey and Frank Sinatra and as a small babyboomer I listened intently to the music of big band and Swing. Now I’m 75 and still listen to it. Maybe it’s was Dad’s genes but I don’t care, the music is wonderful and the greatest generation made it possible for us to enjoy it!

  5. Richard, I think that it is a matter of one coming to the music. No music will come to you; you have to go to it. And if you do, be it Brahms, Bartok or Bunny Berigan, the rewards will be great.

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