Sinatra and Crosby, Singers of Van Heusen Songs, on Picking and Singing Great Songs

Composer Jimmy Van Heusen, right, with frequent collaborator Frank Sinatra, in the 1950s.
Composer Jimmy Van Heusen, right, with frequent collaborator Frank Sinatra, in the 1950s.

NPT and public television fans found much to love in the special membership drive broadcast of Jimmy Van Heusen: Swingin’ with Frank & Bing. The show celebrates the four-time Oscar®-winning composer who created dozens of classics for the American Songbook. His career spanned five decades and his close association with two of the greatest entertainment icons of the last hundred years — Frank Sinatra and Bing Crosby — resulted in numerous hit songs for both. Sinatra recorded over 80 songs by Van Heusen — more than any other composer — including “Come Fly With Me,” “Here’s That Rainy Day,” “The Second Time Around” and “The Tender Trap.”  The 1950s were particularly fruitful for the two, as Van Heusen teamed with lyricist Sammy Cahn to produce such all-time hits as “Love & Marriage,” “All The Way” and “High Hopes.”

Van Heusen’s collaborations with Crosby included the creation of songs for six of the seven Crosby-Bob Hope “Road Pictures,” as well as for the all-time Hollywood classics Going My Way and The Bells of St. Mary’s.

Van Heusen was undoubtedly an outstanding composer. But great composers of great songs also need great singers, and Sinatra and Crosby were the best. But what made them the best? Tucked inside songwriter and radio columnist Nick Kenny’s 1946 advice book, How to Write, Sing and Sell Popular Songs (Hermitage Press), they offer some insight into their craft. A good portion of what they discuss is about selecting the right songs.

Taking a page from Brain Pickings, which does such an excellent job of excavating advice and wisdom from sometimes forgotten books, we thought singers of today might enjoy what Crosby and Sinatra had to say, some 68 years ago. Much of it is timeless, and emphasizes the integral relationship between singer and song.

From PART II of the book, “How to Sing.”


MY ADVICE to the newcomer who wants to sing for radio, records and television is : create a singing style that is different from any other that the pop singers may be using at the time. Too many vocalists are satisfied to be a carbon copy of the current singing favorite. Auditioning directors spot this before the wouldbe artist has gone through eight bars of a song.

Another natural mistake made by most new singers is their rush to sing new songs. Ask any control man. If the pop song of the moment is “I’m Looking Forward To Looking Backward On Tonight,” every second singer on the audition lists sings it—thereby hurting their chances for a real good analysis of their singability. Always pick a song with which you are familiar and one that shows off your voice—not some publishers latest creation. And sing clean songs.

Don’t overlook the importance of phrasing. Learn to throw away a musical line that you would ordinarily punch and vice-versa. Don’t let your singing audience be a few notes ahead of you regarding shading and timing. They like to be surprised. A song is like a bucking bronco. You’ve got to break it in—sing it a hundred times in different ways. Then, after you have memorized the story line of it—tell it in song as if you were enjoying it for the first time. Well there you arc kids . . . spread it among you! . . .


There is no question in my mind that the choice of songs certainly has a great deal to do with the success of a singer. As a matter of fact, very often just one song can give a singer a tremendous boost toward a successful career. “Night and Day,” I think served this purpose for me, and for that reason, it will always be one of my favorites. Back in the early days, it never failed to come through and inevitably got me the job whenever I auditioned with it.

The best advice I can give anyone intent upon a singing career is that they choose their songs carefully. Be sure it is the type of song that particularly suits your style and voice.

I have, personally, always considered the lyric of any song, especially the popular ballad, of number one importance, and I always read the lyric to a new song before I even attempt to hear the music. If it is a ballad, then the words must be believable. They must tell a story. The music is the backdrop or dressing that makes the story pleasant and listenable.

Of course, I don’t mean that every lyric must at all times make sense. It’s certainly not necessary in the case of comedy or novelty songs. Tunes like “Pistol Packin’ Mama” or “Mairzy Doats” have been smash hits, but that’s because they had humor and were farcical enough to catch the ear of the nation.

If you have chosen a song because you really like it and believe it, then you’ve won half the battle towards making others believe it when you sing it.”

How to Write, Sing and Sell Popular Songs is out of print and not available at the Nashville Public Library last we checked, but it’s quite wonderful if you can track it down at a used store.  In addition to advice from Sinatra and Crosby, there are contributions from Irving Berlin, Richard Rodgers, Cole Porter, Cab Calloway, Perry Como and the Andrews Sisters, among others, and sections such as “Ten Commandments for Auditions” and “Let’s Tackle Some Problems.”

And then there’s this from Songwriters Hall of Famer Irving Ceasar, composer of Swanee,” “Sometimes I’m Happy,” “Crazy Rhythm,” and “Tea for Two:

“Most important: Keep writing-writing-writing. One swallow doesn’t make a summer, one song doesn’t make a songwriter. Great writers like Irving Berlin write a hundred or more songs a year, out of which perhaps two or three may become successful. Don’t get the idea that you are better than best and expect sure-fire success from each little bit of writing effort you expend.  KEEP ON WRITING.”

Jimmy Van Heusen: Swingin’ with Frank and Bing is no longer airing this membership drive, and unfortunately, not available as a thank you gift, but we have several DVDs and CDs of his collaborations to choose from when you donate to NPT. A preview is below:

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